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.
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

Cattle Calls & Waterfalls – Glendale Falls

Cattle Calls & Waterfalls – Glendale Falls

Where We Went : Glendale Falls, Middlefield MA

When We Went : Mid-March

Difficulty (Boots 1 – 10) : 3 Boots

Trail Length : 1/4 Mile to the base of the Falls

How Long it Took Us : 1.5 Hours

Overview : For a town with a population of less than 600, Middlefield sure has a lot of history.

The first soldier to ever receive a Purple Heart Medal of honor, Elijah Churchill, a Revolutionary War vet, lived and is buried here.

Martha Stewart laid stakes on Clark Wright Road, humbly purchasing an ,1800’s schoolhouse on 50 acres. Living in this modest homestead without a bathroom or running water from 1966 to mid-1980’s, Martha credits this adventure as the catalyst behind her foray into serious DIY like plumbing, electrical work and contracting as well as some of the happiest times of her life.

The main room was very pretty. It was wainscoted, with a soft, beautiful pine floor. The house had no bathroom, no electricity. We bought it for $15,000, and it was a dream for us. That’s where I really learned how to do everything: electricity, plumbing, gardening, painting, spackling. I tried to build cabinet work in the kitchen and found out I am not a very good carpenter. I’m much better at plumbing.

Click here to read a journal entry where she reflects on fond Christmas memories.

Also located on Clark Wright Road, is Glendale Falls. Previously the site of 18th-century’s Glendale Farm, Revolutionary War veteran Captain Nathaniel Wright, settled on its 400-acres and began farming in 1799. It would remain in the Wright family for over a century.


Clark Brainard Wright, it’s last “wrightful” owner, would operate the farm from 1842 and into the 1920’s. It was under his guidance that the farm became well-known for it’s herd of shorthorn steers.

Most locals have heard of or attended the Middlefield Fair that began in 1855 and still runs over 3 days in August over 165 years later. It was here that this Durham cattle breed won top marks.

Clark Brainard Wright’s “Glendale Duke” was a magnificent specimen that would win top prizes at the Annual Cattle Show of the Highland Agricultural Society (later shortened to the Middlefield Fair). Middlefield was recognized by the Massachusetts Agricultural College (now Umass Amherst) as a leading breeding area:

The show of oxen and steers was the best I have ever seen at a county show, not for the number and perfection of training, but for the size and early maturity; almost every yoke especially of steers, was remarkable.


The cow fair was so legendary that a song was written about it. A lively two-step and male quartet was written by Philip Mack Smith in 1912. It was played at the fair and captures the original essence of the Middlefield Fair as the local folks in attendance must have felt.


The farm and falls were purchased by farmer and conservationist Richard Waite. Nicknamed “Waite’s Falls” during his time there, ,he ,allowed public swimming at the falls, until lewd lawbreakers ruined a good thing. Waite sold the falls and surrounding 60 acres shortly thereafter to the

What We Dug : ,Waterfalls are generally a hit with kids (and grown-ups) and Glendale does not disappoint. This is one of the highest, longest, and most powerful waterfalls in the state of Massachusetts, plunging more than 150 feet. Part of the Westfield River, it’s a rare naturally occurring Class III whitewater run. (For a bit of reference, there are a total of 5 classes in rafting).

At the top of the falls there are some wide, level spaces where you can get a good look at the water hurtling downhill. You can stand at the edge and imagine yourself on a raft with ,four foot ,w,aves shooting up ,,on all sides while the boat careens down the narrow passages.

A short trail leads to the bottom of the falls. The various stairs cut into the side of the trail provide additional tactile interest (i.e. lots of climbing) but please be cautious! There are steep areas that can make for tricky stepping.

It’s always nice to have a “final destination” when you’re out with kids. Having an endgame gives them a mental checkpoint and can be a source of encouragement when spirits start to flag. The bottom of the waterfall is a quick trip from the top but the payoff is spectacular. We spent some time taking it all in before trekking back up the way we came. We finished our afternoon with a few lively games of “Pooh Sticks.”

What We Could Do Without :

This certainly can be a busy destination. Given that there is only one trail up and down the falls it makes “social distancing” or simply enjoying the area on your own next to impossible. If you’re looking for time alone in the woods, this is not the place. Also, if you are bringing along a spirited toddler, be aware that the trail makes it’s way down the side of the cascade. Not so close that there’s fear of toppling in, but for us it certainly was somewhere we had to keep eyes on our kids at all times, not a place to let them run free to roam.

Keep Your Eyes Peeled For : ,Remnants of an 18th-century grist mill on the north side of the waterfall, Hemlock, Birch, Beech, Maple, Hornbeam, Witch Hazel, Shadbush, Mountain Laurel, Painted Trillium, Hobblebush, Warblers

Must Know Before You Go’s : ,No facilities. Seasonal hunting is allowed. A Trustees permit is required. Mountain biking is not allowed. Dogs must be kept on leash at all times.

When enjoying these properties during the Health Crisis, The Trustees asks that visitors follow social distancing guidelines for the health and safety of all, and to help keep properties open in these challenging times:

  • Limit visits to open Trustees properties in your respective town or neighborhood;
  • Stay at least six feet from other visitors, including stepping aside on the trail to let others pass;
  • Please keep dogs leashed and away from other visitors at all times;
  • If a parking area is full, please come back at a less busy time.

Directions : From Pittsfield: Follow Rt. 8 South approx. 5 mi. Turn left onto Rt. 143 East. Follow for 8.1 mi. Turn right onto River Rd. (becomes East River Rd.) and follow for 5.6 mi. Turn right onto Clark Wright Rd. immediately after bridge and proceed 0.4 mi. to entrance and parking (7 cars) on right. Clark Wright Road Middlefield, MA  01243

GPS 42.349, -72.969

Website : www.thetrustees.org/glendalefalls

Resources :

THE MIDDLEFIELD FAIR: A Case Study of the Agricultural Fair in New England (Nineteenth Century)


Scroll through for more pictures of our Glendale Falls adventure!

20 Open-Air Spaces for Berkshire Families

20 Open-Air Spaces for Berkshire Families

With every aspect of our lives suddenly disrupted, nature and outdoor activities provide essential stability, stress-relief and distraction to the current crisis. Lucky for us, the Berkshires is bursting with open-air spaces.

With Spring on the horizon and increasing uncertainties ahead, there is no better time to get outside and let nature work it’s magic.


Here are 20 family-friendly hikes we’ve reviewed to jumpstart your adventures.


  1. Balance Rock State Park
  2. Canoe Meadows Wildlife Sanctuary
  3. Wahconah Falls State Park
  4. Old Mill Trail
  5. Steven’s Glen
  6. Getty Memorial Conservation Area
  7. Mountain Meadow
  8. Pleasant Valley Wildlife Sanctuary
  9. Natural Bridge State Park
  10. Greylock Glen Meadow
  11. Historic Becket Quarry
  12. Ashuwillticook Rail Trail
  13. Dorothy Frances Rice Wildlife Sanctuary
  14. Crane’s Pond
  15. Field Farm
  16. Longcope Park
  17. Road’s End Wildlife Sanctuary
  18. Thomas & Palmer Brook
  19. Bullard Woods
  20. Constitution Hill

Handmade Nature Boards & Inserts available in our Etsy Shop!

COVID-19 Hiking Best Practices

  • Check access before you go, many areas are closed during this time.
  • If you or anyone in your group is feeling sick, STAY HOME.
  • If parking areas are crowded, choose a different space to explore.
  • Give a wide berth to other hikers and allow for at least 6-feet for passing.
  • Practice Carry-In/Carry-Out & Leave No Trace rules. Trash receptacles should not be used.
  • Bathroom and office facilities will be closed to the public.

Treasure Hunting – Mountain Meadow Preserve

Treasure Hunting – Mountain Meadow Preserve

Where We Went: Mountain Meadow Preserve / Williamstown, MA & Pownal, Vermont

When We Went: Last day of August

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

Trail Length: 4.1 miles of trails – Trail surrounding Mountain Meadow is less than 1-mile loop

How Long it Took Us: 2 Hours

Overview: 180-acres of fields and reforested woods make up Mountain Meadow Preserve with portions located in both Williamstown, MA, and Pownal, Vermont. It is owned and maintained by the Trustees of Reservations.

Grace Stoddard Niles spent her childhood exploring that land and in 1902, published The Origin of Plant Names, adopting Greylock as her middle name (from Mount Greylock and Chief Gray Lock). In 1904 she published Bog-trotting for Orchids with her own illustrations. She continued to publish articles on local history and nature. In 1918, at the age of 54, Grace settled on her family’s land but by 1921, her behavior became erratic, and she began harassing her neighbors, culminating in the seemingly deliberate burning down of her own house.

As a result, she would live out the rest of her days at the Brattleboro Retreat (a Vermont mental health facility), and her contributions have been widely forgotten. The well-mowed Niles Trail, Grace’s namesake, leads to the 690-foot elevated grassland where one can gaze across diverse wildflower fields. Spend some time soaking in the spectacular views of Mt. Prospect, Mt. Greylock, and the Taconic Range, that surround this massive meadow. Few landscapes can match the fiery patchwork that transforms the horizon during peak fall.

What We Dug: The short walk from the trailhead to the meadow was filled with excitement. Everywhere we turned, we discovered something new. Monarch caterpillars enjoying the milkweed, gnarled vines to swing on, and a hopping toad hurriedly crossing our path. Autumn days were far from our minds as we marched into the wild expanse of goldenrod and asters, banked among crimson sumac. It was fun telling the kids about an old goldenrod superstition. It’s been said that a person who carries goldenrod with them is destined to find treasure, being a symbol of riches and good fortune. This resulted in a scurry of hands and yellow clutchings, and we spent generous portions of this adventure “treasure hunting” and then doggedly trying to define “superstition” to a 6-year-old – *face palm* (did I say fun?).

Continuing our slow amble around the field; monster grasshoppers, butterflies, and dragonflies galore surprised us at every turn. Veda, our 2 year old, found herself in flower heaven. Stopping to smell the roses (or in this case, the purple asters), takes no prodding when you’re only knee-high. Mason (6), was more difficult to impress. Throughout the hike, he had mentioned (read: repeated every 3rd step), how MUCH he’d LOVE to see a praying mantis. Neither Dan or myself had ever seen a mantis and not knowing much about them (habitat, lifespan, etc.), we did what any sane parent trying to avoid a massive let-down would do – SNACK TIME! This redirection didn’t last (it never does), and before long we were back to muttering our mantis mantra. And ya know what guys? It worked. I shit you not. Somehow that kid conjured a mantis out of the sky. Flying (they fly!) down in front of us was what looked like a white dragonfly. The creature landed on a large stalk and upon further investigation – there. it. was. MANTIS. We could not believe our eyes! It was quite a while before we abandoned our new friend and got back to the trail. Talk about speaking something into existence!

On this brilliantly blue day, the views of the Hoosac Valley and Mt. Greylock were breathtaking. At the top of the meadow the billowy sea of clouds hung almost motionless over the grand hills. With summer swiftly fleeing, you couldn’t help taking the extra time to drink it all in. We followed the loop back to the parking lot and vowed to return in the fall.

Lapses in parental judgment be damned, Mountain Meadow came through with the real treasures that day. Gold is for fools, nature is the infinite prize.

“In every walk with nature, one receives far more than he seeks.” – John Muir

What We Could Do Without: Muddy in spots. If it’s been raining in recent days before your visit, be sure to wear appropriate footwear. Be sure and tuck in your pants and do the pest prevention dance – fields and long grass can be tick-city.

Keep Your Eyes Peeled For: Goldenrod, asters, grasshopper, crickets, mantids, monarch caterpillars & butterflies

Must Know Before You Go’s : Great Birding Locale, No Facilities, Leashed Dogs OK, Cross Country Skiing, Snowshoeing, and Picnicking Permitted, No Bicycles.

Directions : Williamstown parking area: From the intersection of Rts. 2 and 7 in Williamstown, take Route 7 north for 1.7 miles. Bear right onto Mason Street (steep dirt road uphill), follow to entrance and parking. GPS – 42.7385337,-73.2075694

Alternate Entrance/Pownal, Vt. parking area: From the intersection of routes 2 and 7 in Williamstown, follow Route 7 north 1.7 miles, turn right onto Sand Spring Road, then bear right onto Bridges Road Follow for 0.3 miles, turn left onto White Oaks Road, and follow for 1.1 miles when the road becomes dirt. Continue for 0.4 miles, bear left at the fork onto Benedict Road, and continue 0.1 miles to entrance and parking (eight cars) on left.

Website: thetrustees.org

More info on the land’s former history here

Scroll through for more photos of our Mountain Meadow Adventure!