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.

Below you’ll find 20 of our favorite family-friendly foliage locations. These hikes are grouped in order of difficulty, beginning with the most accessible for any age. None of these 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!

With gratitude and humility, we acknowledge that we are gathering, recreating, and learning on the ancestral homelands of the Stockbridge Munsee-Mohican Nation, the indigenous peoples of this land. We invite you to take time to reflect, honor and learn more about our native communities, as well as considering our roles and responsibility in reconciliation, decolonization, and ally-ship.

Click Here to learn more about the Stockbridge-Munsee Mohican Nation.

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. (Limited wheelchair access).  https://threesisterssanctuary.com

Glen Meadow Loop at Greylock Glen (Adams) –  Established in 2017, the packed gravel 1.5 mile Glen Meadow Loop trail takes you around picturesque Greylock Glen. Have fun hunting for the remnants of an abandoned ski resort hidden in the woods and say hi to the birch and willow trees. The wide open views of Greylock and surrounding hills are not to be missed. http://greylockglenresort.com/the-site/greylock-glen-trails

Niles Trail at Mountain Meadow Preserve (Williamstown/Vermont) – At the very end of August, we adventured to this Trustees property and couldn’t get enough of the views! The yellow and purple fields of goldenrod and aster were like a dream to wander through. We are so excited to go back and take in the view of Greylock and the Hoosac Valley during foliage season. With such an easy walk to such a wondrous payoff, you really can’t beat it! http://www.thetrustees.org/places-to-visit/berkshires/mountain-meadow.html


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 that 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. https://www.massaudubon.org/get-outdoors/wildlife-sanctuaries/canoe-meadows

Tourists Public Trails (North Adams) – The trails behind Tourists Hotel in North Adams are open to the public and thank goodness they are! Tucked behind the super chic hotel is a suspension bridge and some fascinating art installations. The meadow view along the Hoosic River is not to be missed. https://www.touristswelcome.com/

Hollow Fields Reserve (Richmond) – After a short jaunt through meadowland, take in the stunning views of Yokun Ridge and the surrounding woodlands. This backdrop in fall transition, is something to see. Hit the woods for a more vibrant walk. Hollow Fields is open between 9:00 a.m. and 5:00 p.m. daily until further notice. 

Diane’s Trail at Gould Farm (Monterey) – Owned by Gould Farm, this 1.5 mile loop trail is located on the property. Grab an interactive booklet at the trailhead. The self-guided tour will take you over bridges, creeks and swamps; alerting you to points of interest along the way. Indulge all your fall senses by paying a visit to the farm’s Roadside Store & Cafe. Delicious, homemade baked goods savored at one of the picnic tables will have you really leaning into the season! Gould Farm  – 275 Main Road, Monterey, MA

 Stone Hill (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. Head uphill for incredible views and a cow or two. Choose from a variety of trails, many short and easy, but all beautiful. It’s hard to pick just one! 

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. An open beach area is a wonderful place for foliage viewing while enjoying a picnic lunch. 

The Pines (Dalton) – Well-worn trails through upland pines, meadow and surrounding pond, The Pines — or as the locals call it, “Happy Land” — has been the extension of many a kid’s backyard over the years (including mine!) Easy walking but no official blazed trails (there are old blazes on some trees) or trail system, so take precautions if you visit. Located off of High Street in Dalton, MA.

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 of a small parking shoulder on Blotz Road, in Pittsfield. Best Day Hikes of  the Appalachian Trail

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. 

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.

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. 

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.


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. Click here to sign-up for our Family Foliage Hike on October 2nd.

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

 Golden Hill Town Forest (Lee) – This 70 acre property was once owned by George Westinghouse, part of his estate known as Erskine Park. The Pinnacle is the highest peak in Lee, offering views to October Mt., Highlawn Farm and Laurel Lake.  Easy loop trails take you through past boulders, ledges, outcrops, wildflowers, mushrooms and old trees. Visit just before sunset and you’ll learn how it got its name!

Shaker Trails (Hancock) – Hands down one of my favorite fall hikes, the trails along the former Shaker religious settlement and sacred site are otherworldly this time of year. Pause for a moment at the reservoir and watch the colorful reflections. If you’re up to it, take the 2.6-mile hike through the golden beech trees to Shaker Mountain and the Holy Site. 

Mahanna Cobble (Lenox/Pittsfield) –  The northern summit of Yokun Ridge, this BNRC property extends into the Bousquet Ski area. Parking is available at Bousquet (except in winter!). Take the far left slope that runs parallel to the Drifter Ski Trail (make sure to turn around and check out the view!) and climb upwards towards 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. The most difficult hike on this list, but boasts the biggest payoff!


Bill Laston Memorial Park & Arboretum (Lanesborough) – Just past the Olde Forge lies a budding arboretum. As leaves start to fall, leaf hunting makes a great outdoor activity. Take a left off of Route 7 and visit the trees at Bill Laston Memorial Park. Click HERE for a FREE printable leaf hunt!

 Check out these Fall Hike Activities to shake things up out on the trail! 

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.