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.