20 Family-Friendly Fall Foliage Hikes

20 Family-Friendly Fall Foliage Hikes

When it comes to fall foliage, nothing beats the spectrum of colors on display in the Berkshire hills. Leaf peepers rejoice as the forested landscape erupts into shades of copper, cornelian, cranberry, gold, and every hue in between. From late September to October, this prismatic flash in the pan transforms any regular, old weekend hike into a dream-like ramble. Gazing at these fiery hills from an elevated vantage point makes us feel fixed in suspension, floating between halcyon days and the edges of change.

These hikes are grouped in order of difficulty, beginning with the most accessible for any age. None of the hikes are over 3 miles, yet some may be more suitable for older children because of steeper ascents and proximity to a ledge. Trust your gut, you know best what your family can handle. Be mindful that fall brings hunting season to some places and packing a blaze orange vest is a cheap and effective precaution.

Enjoy the fall, ya’ll!


Three Sisters Sanctuary (Goshen) – Technically located in Hampshire County, this creative gem is well worth a side trip over the Berkshire borders. Touted as a “place where nature and art merge,” one man’s sensational vision is 8-acres of sculpture gardens and art installations. More of a walk than a hike, you could spend hours here trying to take it all in. In the fall, the area gets fully decorated and the surrounding woodlands are also bursting with color. The fire-breathing dragon is incredible to behold against a clear blue sky. If you’re looking for an interactive, beautiful, and accessible fall walk for any age – look no further.

Niles Trail at Mountain Meadow Preserve (Williamstown/Vermont) – At the end of August, we adventured to this Trustees property and couldn’t get enough of the views! We are so excited to go back and take in the view of Greylock and the Hoosac Valley during foliage season. Check out our review here, there were mantids!

Sacred Way Trail at Canoe Meadows Wildlife Sanctuary (Pittsfield) – One of six Mass Audubon properties in Berkshire County, Canoe Meadows is wonderful in every season. Take the Sacred Way Trail and enjoy a gentle, flat 1-mile trail winds through the sanctuary’s scenic woods, fields, wetlands, and along the Housatonic River. Open fields offer opportunities to take in fall colors. A great spot to bird watch for migrant species during the changing seasons. Fall is a great season to Go Pishing!

Benedict Pond Loop Trail (Great Barrington) – Located in lush Beartown State Forest, this flat 1.7 mile loop is great for all ages and offers beautiful views of serene Benedict pond. Surrounded by dense woodlands, this backdrop in fall transition, is something to see.

Glen Meadow Loop at Greylock Glen (Adams) – Established in 2017, the newer 1.5 mile Glen Meadow Loop trail takes you around picturesque Greylock Glen. The trail is gravel, making walking a breeze. Have fun hunting for the remnants of an abandoned ski resort. The wide open views of Greylock and surrounding hills are not to be missed. One of our favorites in all seasons, we come back here in the spring, summer, and the winter

Wild Acres (Pittsfield) – Climb to the top of the observation tower and take in the surrounding mountain foliage. Located off of South Mountain Road in Pittsfield, Wild Acres is a 1.2 mile lightly trafficked loop neighboring the Pittsfield Airport. 

 

Stone Hill Trails at the Clark (Williamstown) – Part of the Clark Art Museum Complex and owned by Williams College, this is one of the most popular destinations in Williamstown for hiking and enjoying the panoramic views over Williamstown. Check out the trail map for a variety of trails, many short and easy, but all beautiful. It’s hard to pick just one!

Trails at Sheep Hill (Williamstown) – Both the grounds and farmhouse are open year round to the public and a classroom is stocked with binoculars, field guides and other materials to borrow during your visit. There are two trails to choose from – the Rosenburg Ramble which takes you around the perimeter of the property, and the shorter Meadow Walk. Both of these trails offer dramatic views of the valley and surrounding mountains. Rosenburg Ramble is approximately 1- 1.5 miles. The Meadow Walk is a short, easy way to enjoy the views of Sheep Hill, and loops around the pond at the foot of the hillside.

Tyringham Cobble Loop (Tyringham) – Tucked away in tiny Tyringham, this Trustees property includes a 2.1 mile loop trail running through a combination of meadow and forest. Keep an eye out for the aptly named Rabbit Rock! A well-marked trail leads to a spectacular view of the valley at the summit. See if you can spot the quaint Tyringham churchyard from the top!

Warner Hill (Hinsdale/Pittsfield) – Part of the AT, this easy up-and-back hike is 1.4 miles, ideal for families. Head through a dense evergreen forest, crunch through fallen maple and beech leaves along old stone walls, and finally to Warner Hill, where the summit offers a view of Mount Greylock on a clear day.The trailhead is right off a small the parking shoulder on Blotz Road, in Pittsfield.

Rounds Rock Trail (Cheshire) – Part of Mount Greylock State Reservation, Rounds Rock is a great spot to tackle a less strenuous hike at Greylock. This 0.9 mile trail is a moderately trafficked loop and is good for all skill levels. The remains of a 1948 plane crash and its memorial is a point of interest. The hike reaches its peak with two scenic vistas offering gorgeous autumn views.

North Trail at Field Farm (Williamstown) – Nestled in the valley between the Greylock and Taconic ranges, you’ll find another Trustees property. Field Farm boasts a pond, caves, sculpture garden, and two modernist style homes all located onsite. North Trail is a popular hike, a mile long trail that encircles the central pasture and shows off jaw-dropping mountain views in all directions. Another trail, the Caves Loop, will enchant any imagination, no matter the age. We enjoy visiting the beavers during the winter months, too.

York Lake Loop Trail in Sandisfield State Forest (Sandisfield) – This loop trail encircles the lake through dense woods and busy wetlands. The trail is 2.2 miles long and can be wet in places depending on the weather. The open beach area is wonderful place for foliage viewing while enjoying a picnic lunch.

 

Laura’s Tower Trail (Stockbridge) – A 1.5 mile out-and-back hike that begins with a quiet walk through an old pine and hemlock grove. Boulders crop up on the wide trail towards yellowing birch trees. At the top of your climb you will reach a metal observation tower. Take the stairs to take in breathtaking panoramic views of Mt. Greylock, The Catskills, and Vermont’s Green Mountains. 

 

Sunset Rock Trail at Hoosac Range (North Adams) – Part of the Hoosac Range, this short 1.6 mile round-trip hike has a small steep portion, but a big pay off, with views to the west and north, overlooking North Adams. The BNRC parking lot is on the right, immediately after the Wigwam Cabins.

Summit Trail to Pony Mountain at Chapel Brook (Ashfield) – Summit Trail is a steeper 0.5 mile hike that leads around the western side of Pony Mountain to its top, where incredible panoramic views of the foothills of the changing Berkshires can be taken in.

 

Mahanna Cobble (Lenox/Pittsfield) – The northern summit of Yokun Ridge, this BNRC property extends into Bousquet Ski area. Parking is available at Bousquet (except for winter!). Take the far left slope onto the Drifter Ski Trail (make sure to turn around and check out the view!) and climb upwards to the highest chair lift (so many VIEWS!). Continue past the radio tower to a 1/4 mile trek through the woods. The summit opens up to a stone bench and MORE glorious views.

Basin Pond (Lee) – From the trailhead, the 2.5 mile route takes hikers on an easy ramble alongside boulders and stone stairs. The trail splits but converges again at a short spur that leads to the ruins of a twice-flooded dam. Either trail you choose doesn’t require much exertion. A lookout platform offers a terrific spot to view the ruins, the beaver pond, and all the vibrant colors of autumn.

Drury Trail at Drury Preserve (Sheffield) – Approximately a 3-mile walk, up and back, through lowland forests, and a variety of wet and dry communities. There are boardwalks over the wettest areas, and at the end of the trail, take in a striking view across Schenob Brook of Taconic Range’s Mount Race.

Dry Hill (New Marlborough) – Owned by the Trustees, this is a 2-mile out-and-back trail of mostly flat and easy walking.The oak forest that covers the upper ridge is awash with color during the autumn months. The last few minutes to the summit are a bit steep and rocky, but well-worth it for the unmatched fall views.


What adventures are we missing out on?

Do you have favorite foliage hikes or fall spots in the Berkshires?

Share in the comments below!

Tag @berkshirefamilyhikes in your fall foliage pics on Instagram and Facebook! Use the hashtags #berkshirefamilyhikes and #fallinlovewiththeberkshires

Safe Covid-19 Hiking Practices 

  • Visit parks and recreation areas that are close to your home.
  • Don’t visit crowded parks or campgrounds.
  • Carefully consider use of playgrounds, and help children follow guidelines.
  • Stay at least 6 feet away from people you don’t live with.
  • Wear a mask.
  • Wash your hands often and don’t share items with people you don’t live with.
A Dream Forgotten – Getty Memorial Conservation Area

A Dream Forgotten – Getty Memorial Conservation Area

Where We Went: Getty Memorial Conservation Area & adjacent trails, in between Nessacus Middle School & Wahconah High School in Dalton, MA

When We Went: Late May & August (school WAS out!)

Difficulty (Boots 1 – 10): 0.5 Boot / 1 Boot

Trail Length: Undetermined / shortest trail to conservation area is about 200 yards

How Long it Took Us: 2 hours

Overview: Alright. Ready? I’m gonna attempt to break this area down and also serve it the long-forgotten justice it deserves, SO – bear with me. If you’re looking for just the basics of this hike, skip down to What We Dug. Otherwise strap in, ’cause off we go…

In 1972, Raynard Getty, a high school science teacher, began developing 50 acres behind the Dalton school into a conservation area. In conjunction with classroom studies, Wahconah students, alongside Getty, worked on extensive plans to create a wildlife refuge, 4 1/2 miles of nature trails, two tree farms, a large fieldstone fireplace, and a small pond. A teacher truly ahead of his time,

Getty described his vision as, “a quiet area where students can go to think and meditate.

Students constructed a 22-foot bridge over a drainage ditch that same year. In 1975, the U.S. Navy “Seabees” helped the students dig a 1/2 acre farm pond. Maple, chestnut and other trees were planted with intention of fostering a tree nursery. It’s aim was two-fold, to provide replacement trees to the town and give young people the knowledge of tree care from the ground up. Seven large fieldstone planters were built by students and filled with numerous flower varietals they had been consciously raising indoors. Brush was cut and cleared (teenagers with chainsaws!), benches built, and large stones were relocated to create stone walls. All of this structured towards specific goals, but with kids being the integral part of the program.

Then in 1981, at the age of 52, Getty passed suddenly of a heart attack. He may have only succeeded in developing 20 of the 50 acres planned, but his gifts to the community far exceeded that. What he left behind were inspired students who had learned everlasting skills of perseverance, consideration, and stewardship to take with them into adulthood. An enormous feat for a man with just a humble plan. Later that year, various science classes conceptualized and created a nature trail in Getty’s honor. Together they located, identified, and described 21 different points of interest within the conservation area and trail. Trail markers were built and erected and informational pamphlets were made and distributed at the area’s memorial.

It’s been said that, to hear is to forget, to see is to remember and to do is to understand.

Mr. Getty organized and bonded with these students to give them a chance to work outdoors and learn first-hand about caring for the environment. He helped them build something of value, transforming and nurturing the woods surrounding their school.

With the Earth’s current environmental future in a precarious balance, let this serve as a reminder to how impactful a mentor can be.

Over the years, much of this area has not seen the level of care intended for it, nor have steps been taken to complete Raynard Getty’s vision. The pond is overgrown, trails are no longer marked, and any points of interest have been reclaimed by the woods. Most recently, local Eagle Scouts cleaned up the main conservation area. Led by high school senior Jack Minella, they also built new benches and additional raised beds. With the new school year just beginning, perhaps new efforts will be put forth to rejuvenate such a unique and worthy space. Maybe all it’s waiting for is that one special voice to spark change.

With all of this (so much this), being said, do not expect one of those map at the trailhead, blazes on every 8th tree, kinda hike. For this one, you’ll have to use a tiny amount of self-navigation but your efforts will be well rewarded. The main trails here are wide, well-trodden, and generally all circle back around to one school or the other. But be aware that they are not marked! Even if you can’t find your way out of a paper bag, the conservation area alone is worth the trip. Pull up a bench, take in your surroundings, and meditate for a minute on what one man’s fleeting influence can do for the world.

What We Dug: We drove to Nessacus Middle School and chose to drive around to the back of the school, past the basketball and tennis courts, where a few parking spaces face a large wooded area. (School was out for the summer). Once out of the car, you’ll see a large open space containing a drainage dug-out to the right of a utility garage. We spent some sunshine-y minutes rolling down this grassy hill and picking dandelions. After getting good and dizzy (1 roll was all it took, holy motion sickness batman!), we started off down a familiar ramble. Most Daltonians know of the path I’m referencing, a shortcut taken by many on Friday night during football season. For others, if you stand in the field with your back to the school, the trail I speak of will be facing you and difficult to miss.

Following a (very) short trek, the trees will begin to open up and you will find yourself in the wide open green of the Getty Memorial Conservation Area. If you continue straight over a small wooden bridge you will see Wahconah High School and it’s football field directly in front of you.

Now you’re probably thinking, “that’s it?” “Less than a 2 minute walk?” WAIT. There’s more. We spent some time exploring the conservation area. At that time it hadn’t undergone any maintenance and the pond bridge and other parts were overgrown. After a snack (BECAUSE ALWAYS), we took a left onto a wide trail. There are no markers or blazes on these paths and many offshoots. However, it would be VERY (not impossible, but…) difficult to get lost. With the two school bookending this forested space and the Housatonic river cutting through to the east, regaining your bearings is fairly simple. Most of the trails spit you out at the backside of one school or the other.

In recent years, the trails have seen the addition of outdoor exercise equipment distributed within the woods. Pull up bars, parallel bars, and balance beams became instant jungle gyms for the kids. Searching for the next one kept attentions from flagging. Winding around the side of the schools is the East Branch of the Housatonic river. Through a dense and impressive pine grove you can (carefully) climb down a small embankment to the gravelly-edge of the river. Here we skipped stones and examined abandoned stonefly nymph exoskeletons that they leave stuck to sunny rocks. Heading back to the trails and we found ourselves back at Nessacus, at the edge of an expansive soccer field. To round out a low-impact adventure, the kids chose to run around the basketball courts. Far be it from me to refuse an opportunity to release some MORE energy (like, how. is. it. possible.)

What We Could Do Without: The lack of defined and marked trails make this less accessible for anyone who may be unfamiliar with the area. It would be so wonderful to see Raynard Getty’s full vision brought to life.

Keep Your Eyes Peeled For: Hemlock, white pine, milkweed, monarchs, crayfish, stonefly nymphs

Must Know Before You Go’s: There are no trailheads. No markers or blazes. Be aware that barring summer months, both schools are in session. Wahconah High School is currently undergoing construction. Parking there is not recommended. Due to Covid-19, re-opening of these schools is still unclear, but use sound judgement. Summer and weekends are the best time to explore these trails. No facilities.

Directions: 35 Fox Rd, Dalton, MA 01226 (Nessacus Middle School)

150 Old Windsor Rd, Dalton, MA 01226 (Wahconah High School) Be advised that Wahconah High School is currently undergoing massive construction and parking there is not recommended.

*Entrances to all trails are towards the back ends of both schools.

Scroll through for more photos of our Gettys Conservation Area Adventure!

Community FB page

Top Hikes for Accessibility in the Berkshires

Top Hikes for Accessibility in the Berkshires

Being outdoors and in nature is beneficial in so many ways. From healing health benefits, building community connections, education, or just having some fun, the outdoors is a gift. And that gift should be available to everyone. But for many people with disabilities, mobility limitations, and even parents with strollers, outdoor recreation can feel preclusive because the expectations are unknown. The thought of getting outdoors raises worries – What is the trail like? Is it paved or gravel? Is there service in case of an emergency? The Berkshires is home to so many incredible outdoors spaces. But how many of them are accessible to all?

This list is in no way comprehensive. It lacks in covering many pertinent details that we have limited to no insight on. It is intended as a starting point for disabled people, friends and family of disabled people, parents of young children, and elderly people. It is up to us to create inclusivity for all – in nature and beyond. We’d love to hear what we can do better and welcome shared experiences and challenges when getting outdoors. Email us at berkshirefamilyhikes@gmail.com or join us in the Berkshire Family Hikes Community Group.

A wonderful resource is Everyone Outdoors, a community resource blog and recreation connection for people with disabilities and their families, friends, and supporters who enjoy the outdoors, are looking for new recreation possibilities, or want to share their experience and expertise with others.


  • Ashuwillticook Rail TrailThe only thing intimidating here is the name! Ash-u-will-ti-cook Rail Trail is an old railroad track converted into a 10-foot wide paved trail. The trail runs 12.7 miles through the towns of Cheshire, Lanesborough and Adams. Various access points and parking lots make for multiple entrances into the outdoors. Cheshire Reservoir, and the Hoosic River offer outstanding views of the scenery and wildlife. We’ve hiked it in the rain and lucked out seeing a snapping turtle!
  • Pittsfield State Forest – Located off of Berry Pond Circuit Road, the paved Tranquility Trail is a 0.6 mile loop. It features a peaceful forest setting and is good for all skill levels. The trail is primarily used for hiking, walking, and nature trips.
  • Old Mill Trail One of our favorites, this unpaved gravel trail is great for beginning hikers, families with young children, strollers, and some mobility limitaions. The first 0.7 miles is an accessible trail that follows the Housatonic river north. The trail continues for another 0.8 miles but is not considered accessible. There is a bridge crossing in the beginning of the trail.
  • Greylock Glen – The Glen Meadow Loop at Greylock Glen is a flat, gravel covered 10-foot wide loop which winds its way around the main part of the Glen for 1.6 miles. According to information from EveryoneOutdoors, “this trail is best accessed by driving past the parking lot on Gould Road (from this access point there is a climb to reach the loop trail) and continue driving uphill around a curve, past the small parking lot for Peck’s Falls on the left, to a second parking area for the loop trail on the right. It’s roadside parking on a hill, so it is not considered accessible, but for some it might be worth it because if you can handle the parking angle, it is possible to pass through the roadside boulders (45″ width” passage) to enter the loop trail area.” The views of Mount Greylock and the surrounding hills are unbeatable as well as the huge willow tree.
  • Mary Flynn TrailThis trail in Stockbridge begins with a 100-foot long boardwalk before continuing on a flat, gravel trail through woodlands of birch, pine, and cottonwood. There are two wooden bridge crossings. At the far end, the trail curves, narrows, and loops back alongside the Housatonic river, crossing two small bridges before rejoining the main gravel trail.
  • Parson’s Marsh – The first 600-feet of Parson’s Marsh in Lenox is crushed stone. Gentle slopes lead you to an accessible picnic table and bench off a short spur near the pond. According to EveryoneOutdoors, “the last section of the trail is 900-feet of curbed boardwalk, with a 41” passable width and grades not exceeding 7%.” The trail ends at an observation platform with views from the edges of the marsh.
  • Taconic Farm Estate/Tor CourtOnce a mansion home to Warren Salisbury and the site of a manhunt that ended with John D. Rockefeller’s subpoena, this verdant hilltop is now owned by Hillcrest Hospital. Drive around to the back of the hospital where a large parking area gives easy access to a paved path among the trees. The gazebo is not accessible (stairs only) but is a beautiful feature. The paved trail is not very long and you will have to back track in order to return to the parking lot, but the views of Onota Lake and the surrounding woodlands make this a low impact way to get outdoors. 165 Tor Court, Pittsfield, MA 01201 
  • DAR State Forest – This easily navigable trail in Goshen is dirt-packed and shaded, with tranquil views of the water. The trail is 1.1 miles, ending on a paved road. If you are looking to fish, there are three accessible fishing spots along the trail with sturdy metal docks out to Upper Highland Lake. If you will be parking at the DAR State Forest with a wheelchair, don’t use the public beach parking lot (the first lot upon entry). Continue following the driveway until you reach another paved lot on the left, giving you direct access to the trail without a trip around the beach. 
  • Savoy Mountain State Forest – The accessible trail starts from the main parking lot. Pass the closed restrooms you’ll find a paved path through the main area of the park. A left will take you to a picnic area and an accessible path to the beach. A right will take you to the trailhead sign for the accessible woodland North Pond Loop trail. Old stone fireplaces are visible along the trail. At the junction, bear left and loop around back to the paved road, returning to the parking lot via the paved road.
  • Pleasant Valley Wildlife SanctuaryThe All Persons Trail at Pleasant Valley is 1,700 feet in length roundtrip from the main office to Pike’s Pond. It is fully accessible and follows a wide path with a smooth, packed surface before leading to a boardwalk with views over Pike’s Pond. The trail is mostly level with a few moderate slopes. Narrated stops along the way are marked by signs both in print and in Braille. Prior to Covid-19 and the closure of facilities, you could pick up trail information including a guide in printed or Braille format, and a printed or tactile trail map, as well as other adaptive items, including hands-free binoculars (on a tripod), audio players, a large print version of the “Peterson Field Guide to Eastern Birds,” and a walking cane with a small seat. Currently the offices and other facilities are closed. 
  • Mount Greylock State Forest – Sperry Road to Stony Ledge Trail is a 1.9 mile out and back gravel road. Sperry Road is a well-maintained dirt road that takes you to the scenic lookout point offering beautiful views of Mt. Greylock and other mountains. Facilities and campgrounds at Mount Greylock State Forest are closed due to Covid-19. 
  • John Lambert Nature TrailTucked behind the Ralph Hoffmann Environmental Science and Sustainable Energy Center at Berkshire Community College, the John Lambert Nature Trail wanders through open fields. The meadow portion is well-mown but does have some slight grades and curves that make certain types of accessibility more difficult without assistance. The entrance behind the Hoffmann Center is NOT wheelchair accessible. There is a partially paved entry point just across from Melville Hall. This entry has a slope that may effect accessibility. This route will take you to trailhead behind the Hoffmann Center, so it may be necessary to turn around and retrace your route to get back to the parking lot. 1350 West Street, Pittsfield, MA 01201

Non-Accessible Entrance

Non-Accessible Entrance

More Accessible Entrance

More Accessible Entrance

 

 


As more places continue to open, we all must do our part to follow new rules about how to responsibly return to the trails. Though your chance of getting COVID-19 in the outdoors is low, you still need to bring a mask, take social distancing precautions, and wash or sanitize your hands more frequently. If you are feeling sick, please stay home.

Pooh Sticks Paradise – Margaret Lindley Park

Pooh Sticks Paradise – Margaret Lindley Park

Where We Went: Margaret Lindley Park – Williamstown, MA 

When We Went: Early May 2020

Difficulty (Boots 1 – 10): 1 Boot

Trail Length: 0.85 miles, Yellow Blazes

How Long it Took Us: 1.5 Hours

Old Aerial View

Overview: Margaret Lindley Park is tucked away in the Southwest corner of Route 7 and Route 2 in Williamstown. Named for longtime area educator Margaret Jones Lindley, the park’s 13.5 acres were purchased and dedicated shortly after her death in 1966. The park features expansive woodlands, picnicking, and a man-made swimming pool that is filled during the warmer months and has historically served as a popular cooling-off spot for residents over the years. Due to Covid-19, the town made the difficult decision to hold off on filling it this year.

Don’t let this dissuade you from exploring the park’s trails and woodlands. Williamstown Rural Lands Foundation has been a steward of these trails since 2011. Follow along the banks of Hemlock Brook, a water source that originates in the Taconic Mountain Range before emptying into the Hoosic River or walk the cool shade of the towering Hemlock Grove. 

 What We Dug: Right from the parking lot, we were struck by the presence of an enormous silver maple tree, it’s red buds visible against the brilliant blue sky. M & V made a bee-line for the retaining columns at the edge of the empty swimming area and in a jiff were sitting proudly at the top. After a cautious descent, they made tracks in what M called, the “giant sandbox.” We found the Hemlock Brook/Torrey Woods Trailhead on the far side of the swimming pond near the edge of the woodlands. From there we followed the blue blazes a little ways until we got to a 4-way intersection.

On our left was a red-blazed trail that we soon discovered led through the Hemlock grove and back to the parking area. Over the bridge to the right is the other half of the Torrey Woods Trail. Because Torrey Woods Trail encompasses the Hemlock Brook Trail and the kids were dead set on playing Pooh Sticks on the bridge, we continued our hike to the right. Following yellow-blazes now, we continued along brookside, making ample use of several opportunities to explore close to the water and throw stones. It was too early for tadpoles, but the kids had fun searching the weeds anyways. Crossing a second footbridge the trail becomes Hemlock Brook Trail again and we raced our sticks a 2nd time. Soon enough, we crossed a third foot bridge and a fourth, finally concluding our Pooh Stick tournament of champions.

Hopping back across the brook via some large stepping stones was a little slippery, V got wet but I’m pretty sure it was intentional lol. A the far bank, keep left to head back to the Park. You’ll see a sign alerting you that you are leaving Williamstown Rural Lands Foundation property and it’s straight on back to the Park. We finished out our adventure by walking the Hemlock Grove trail back to the parking lot and marveling at the sheer size of some of the trees. Some of them are over 100 years old! If you’re looking for a place to let the kids loose and explore, you can’t beat Margaret Lindley Park. 

What We Could Do Without: When we visited in May, we didn’t think too much of the swimming area in regards to the global pandemic. It was too early to swim and Covid still seemed like a temporary inconvenience that would be sorted in no time at all. Cut to August and everything’s still closed, we’re gearing up for remote learning, and our Berkshire bubble is a maze of masked mortals waiting for the other shoe to drop. The only thing I could do without these days is the constant reminder of all the things we took for granted before the pandemic. 

Keep Your Eyes Peeled For: Eastern Hemlock, Silver Maple, Striped Maple, Paper Birch, Carolina Spring-Beauty (spring), Fiddlehead (spring), Mapleleaf Viburnum, Mosses & Lichens, Chipmunk, Tadpoles, Red Efts

Must Know Before You Go’s: Facilities are currently closed to the public. Dogs are OK but must be leashed. Swimming is not available at this time. Always practice carry-in/carry-out and leave no trace principles when visiting nature and the outdoors. Social-distancing guidelines help keep everyone safe & healthy to enjoy the trails. 

DirectionsMargaret Lindley Park, 1201 Cold Spring Rd, Williamstown, MA 01267

From the intersection of Rts. 2 and 7 in Williamstown (the roundabout), take Routes 7 and 2 southwest for 2.3 miles. Turn right into Margaret Lindley Park just after Route 2 leaves Route 7 (2.31 mi.).

Website: Williamstown Rural Lands Foundation

Resources: Margaret Lindley Park Facebook Page

The Caveman Cometh – Tory Cave Falls

The Caveman Cometh – Tory Cave Falls

Where We Went: Tory Cave Falls – October Mountain State Forest, Lenoxdale, MA

When We Went: Mid-June 2020

Difficulty (Boots 1 – 10): 2 Boots, (3 Boots to get to the cave)

Trail Length: Just over 0.5 miles roundtrip

How Long it Took Us: 1.5 hours

Overview: According to writer and connoisseur of the Berkshire unusual, Joe Durwin, the use of caves as refuge was in fact, not unusual. “Caves were the original literal criminal underworld. Berkshire County has more active or “live” caves than any area in the Northeast. Tories, counterfeiters, bootleggers, “wild men” and others have all recycled them for their needs.”

And in 1776, no one needed a rocky refuge more than Stockbridge resident, and local tavern owner Gideon Smith. Smith was a Tory, a loyalist to the British crown, and his tavern (located where Wheatleigh stands today), was a popular rendezvous spot for Tory messengers passing through from Albany to Springfield in the 18th century. Then in May of 1776, Smith harbored a British POW, Captain McKay, in his home and the neighboring rebels were out for blood.

So what’s a British loyalist to do? Break for the hills and hunker down in a cave until you’re in the clear. Rumor has it that the Mohican’s brought him food and that his wife would travel nightly four miles by arduous route to parade the children by the cave on a daily basis, just to show him they were well and safe. But clear never comes for Gideon. Foolishly sticking his head out of the cave one day, he was discovered! Caught and captured, he was put to the noose three times. According to “A History of Berkshire County,” “Having fastened a halter around his neck, he was attended with due solemnity to a signpost, pulled up and suffered to remain until nearly defunct.” Told he must renounce his Tory ways, Gideon held on until the third time, saying he would “swing his hat in favor of the Colonial cause.”

The deHeredia’s, former owners of Gilded era mansion Wheatleigh, found the original Smith tavern sign on the property and gifted it to the Stockbridge Historical Library in 1902. In 1782, Gideon left another mark, purchasing a grassy knoll on Mahkeenac Road for the use as a family burial ground. Quietly overlooking the Stockbridge Bowl, it’s curious that he is not among the 22 burials and his final resting place is unknown. Gideon was 98 when he died in 1838.

Another tale, more interesting to me than Gideon’s, is about the Caveman & his sweetheart. In 1932, the cave was used as a trysting spot for two star-crossed lovers, Lenoxdale’s own Bonnie & Clyde. Sixteen-year-old Myra Holmes and eighteen-year-old Albert Felix ran away from their homes one a Friday evening in May and were missing for a week. Extensive searches were held but only glimpses of the fugitives were to be had. One Eagle headline read, “Youthful Caveman Raids Iceboxes to Bring Back Food For Young Sweetheart.” A diary was found inside Tory cave detailing the story of the couple’s escapades, including Felix’s clandestine trips to “Shacktown to get some bread, coffee, sugar, and milk.”

They were eventually found in Albany on June 3rd and returned home to their parents.

But young hearts can’t be broken. And on July 2nd, 1932, the pair ran away again!

This time they took refuge in the partially finished James Brattle Burbank house on Williams Street in Pittsfield. As icebox items started to go missing in the neighborhood, the jig was up. On July 5th, police officers raided the residence where they found Myra and Albert armed with both rifle and revolver. After a short stand-off, both were arrested and charged with various crimes, including Myra’s additional charge of “being an exceptionally stubborn child.”

For another caving adventure, check out “Gold-Diggers & Cave Crawlers

What We Dug: If there are hiking and history involved, you know I’m thrilled. Tory Cave did not disappoint. The trail to the waterfall and cave was mild and mostly easy walking. Some portions of the trail were washed out from recent rains and there were a few fallen branches to navigate around. As the path starts to go uphill, you will pass a trail for Dewy Hill on your left-hand side. Just after this path on your right, is a footpath that goes down to the stream. Be cautious! Although short, the path down can be fairly steep and unreliable for sure-footing. The cave is not visible from the trail and we found we had passed right by it. Farther up the stream were easier access points where the kids enjoyed wading and rock climbing before we turned around and hit the cave.

Calling it a cave nowadays seems overly generous. In 2013, the rain from Hurricane Irene flooded Roaring Brook and eroded any remaining cave that was left after the landslide. The area is a little tricky to get to but the beauty makes it worth the fumbling footwork. I can almost see Myra and Albert splashing each other at the edge of the pool, wary of snapping twigs coming to interrupt their idyllic getaway. I wonder what happened to those two…if they ever ended up together or were doomed from the start.

What We Could Do Without: It was hot and humid. Add water to the mix and you’ve got mosquitoes. Buzzing, bloodthirsty blaggards, impervious to the densest plumes of repellent. I actually think some of them like it. Skeeters put a damper on shit for sure but we just keep marinating in citronella and hoping for the best.

Keep Your Eyes Peeled For: Walking ferns, hemlock, pine, red efts, wood frogs, mountain wood-sorel, water striders, rainbow and brook trout

Must Know Before You Go’s: Parking and trailhead are just before a small bridge. There is no parking area so use caution when parking on the shoulder. Trailhead heads east upstream along Roaring Brook. No facilities. Leashed dogs okay.

Directions: From Route-7 in Lenox, turn onto, heading east on New Lenox Road for 1.8 miles. At the intersection of East New Lenox Road and New Lenox Road, turn right onto Roaring Brook Road. Head south for 0.4 miles, just before a small bridge. Trailhead is to your left. GPS: N422316.08 -W731416.17

Website: October Mountain State Forest

Resources: lenoxhistory.org, “History of Berkshire County” by Godfrey Greylock, Berkshire Eagle Oct. 31, 1976, Berkshire Eagle May-July, 1932, These Mysterious Hills – Joe Durwin

Gold Diggers & Cave Crawlers – Widow White Reserve

Gold Diggers & Cave Crawlers – Widow White Reserve

                                             
Where We Went : Widow White Reservation – Lanesboro, MA

When We Went : Early April & again in Late May

Difficulty (Boots 1 – 10) : Steep in places, but mostly easy walking on wide wood roads 2.5 Boots

Trail Length : NO MARKED TRAILS, wood roads are generally clear enough to follow

How Long it Took Us : 2.5 Hours

  Overview : A revenge rock and a cave – two things you wouldn’t be expecting    to see on a walk in the woods, but that’s exactly what you’ll find at Widow White Reserve in Lanesboro, MA.

What’s a revenge rock, you ask? Well, it’s apparently how you express yourself when you’re an scorned windbag with some mean chiselin’ skills. Meet Captain John Brown. Born in Cheshire, Brown was a hot-headed stonemason. He was leader of the Cheshire militia in the 19th century. That is until he disbanded said militia because at a meeting he wasn’t called on first to speak…just to give you an idea of what we’re dealing with here, Petty with a capital P.

Enter Susan Baker. This gal was the richest woman in Lanesboro for many years. She owned Baker’s Tavern on Greylock Road, a popular stage coach inn frequented by travelers over Brodie Mt. highway. Susan also owned a multitude of marble and wood rich acres on Potter Mountain (location of Widow White). At 81 when 69 year old John Brown came ‘a courtin’, old Sue probably couldn’t bring the hammer down fast enough! I mean, the man had 10 children for pete’s sake – if he’d been more transparent he’d be cellophane. Now I ain’t sayin’ he’s a golddigger. But yes. Yes I am.

Johnny had his pride bulldozed and instead of shooting his shot and taking it on the chin, Mr. Brown decided to go for the King’s crown of pettiness – packing his trusty chisel and a whole bag full of bruised ego, he walked from Cheshire to Lanesboro, to the edge of Susan’s property and on an errant boulder chipped away this message:

“Capt. John M. Brown, Born at Stafford’s Hill, Cheshire, Mass., Oct. the 1st, 1808; inscribed upon this rock, April the 2d, 1878. May God bless Susan and all her barren land and when she gets to heaven, I hope she will find a man.”

Whewww, SNAP! Can you taste the bitterness…

john brown boulder

Brown’s Boulder in the 1970’s (Berkshire Eagle)

john brown boudler

Brown’s Boulder Present Day (BFH)

Four years later, Susan died, aged 85 and completely unbothered (my assumption).

But do you know who wasn’t?

YUP.  Old John “dog with a bone” Brown, that’s who. He wrote a follow-up to his original inscription. Although he never took the opportunity to gouge it into stone for all eternity, his family saved the verse and I offer it to you now:

“Now Susan has gone to her long home. It makes me sad, it makes me mourn. What a mighty shock, when I view this rock, to know that I am still alone.”

Good call, Sue – safe to say you dodged a bullet on that one.

(North Adams Transcript)

On the uphill path to Brown’s Boulder, you’ll pass by Baker’s Quarry Cave near a stand of white birches. Named for village belle Susan Baker, this modest hole in the ground doesn’t look like much. But for a spelunker like Clay Perry, caves like this were an underground wonderland. Clay Perry was an author and journalist, a transplant from Wisconsin who moved to the Berkshires in 1912.

An avid cave crawler, Clay explored over 200 Northeastern caves, wrote three books on the subject, (“Underground New England” “New England’s Buried Treasure” and “Underground Empire”) and even coined the term “spelunker!” (Note : If anyone has a copy of one of these books, please contact me! For armchair spelunking only.) Baker’s Quarry was Perry’s favorite cave and he led many conventions here for other cave-crawling enthusiasts. The cave stretches 150-feet and has been visited since 1847 if the inscriptions carved into the walls are any indication. The cave entrance was likely discovered when marble quarrying was done on this property, remnants of which you can also find. The brook nearby is aptly named Disappearing Brook, which disappears and reappears six times over a mile stretch.

I would NOT recommend going inside the cave. Cave-crawlers and spelunkers are serious hobbyists and professionals who know the risks and the equipment needed. If you’re curious about what’s inside,  check out this video Brad Herder took of the inside in 2013.

What We Dug : Would you believe that we didn’t see Brown’s Boulder or Baker Quarry Cave until our return trip? It’s true. We were on the hunt for both but somehow kept circling around the very things we were searching for. During that first trip the trees were bare and the glacier erratics stole the show. Everywhere we turned there was a bigger boulder than the last, another rock to climb, another outcrop to conquer. When we returned, we were on a mission. It was one we accomplished and truly enjoyed – who doesn’t love a good mystery hunt – but cave or no cave, Widow White is such a cool place to explore.

What We Could Do Without : The first time we visited Widow White, the trees were still budded and the forest floor was mostly clear, save for a few early spring ephemerals. What a difference a month makes! Widow White doesn’t have maintained trails but the wood roads make for easy walking.

Widow White in April

Widow White in May

Still, when we returned in May, it was full bore glorious spring and we found that the wood roads can get a bit lost underneath the new growth. Beyond being absolutely stunningly green everywhere you turn, it can be easy to get turned around, so please you caution, good judgment and a map.

Keep Your Eyes Peeled For: Captain John Brown Stone, Baker’s Quarry Cave, the remnants of a mill dam on Secum Brook, small quarries and an extensive stone wall, spring ephemerals like trillium and hepatica, jack-in-the-pulpit, birch groves, snails

Must Know Before You Go’s: Hunting is allowed in-season. Wear reflective clothing and take precautions. No Facilities. No Marked Trails. Silver Street is a dirt road and the parking lot is unpaved.

Directions: Widow White Reserve is accessed from an unimproved trailhead off of Silver Street.
From the center of Lanesborough: north on Route 7 to a left on Bailey Road. Follow Bailey Road north for 1.0 miles to a left on Silver Street. Follow Silver Street for 0.4 miles to the trailhead, which is at the top of a short steep hill, on a very sharp left-hand curve. Trailhead is on the right at the curve. GPS: 42.5472, -73.2520 (trailhead parking)

Website : https://www.bnrc.org/wp-content/uploads/2016/10/WidowWhite_TrailMap.pdf

Resources : https://mysterious-hills.blogspot.com/2010/03/recalling-perry-explorer-of-berkshire.html

https://www.youtube.com/watch?v=42Ate6oC-Rc

Scroll Through for More Pictures of our Widow White Adventure!