10 Berkshire Fall Foliage Hikes For Families

By Taylor Staubach - Berkshire Family Hikes September 21, 2022

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.

Here you'll find 10 of Berkshire Family Hikes' 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. For 10 more fall hike ideas, fall activities, and more, check out

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).

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.

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.

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.

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!

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

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.

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.

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!

 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!