The Berkshires have a way of making childhood feel unhurried. There's space here — meadows, trails, open water, and quiet village streets — and an abundance of experiences that don't require much more than sunscreen, good shoes, and a sense of adventure. Whether you're a local family or visiting for the weekend, this corner of Massachusetts delivers something meaningful in every season.
We've put together a full guide to the best free and low-cost family-friendly activities in Berkshire County — organized by season, with ages, locations, and links to plan ahead. Download the full guide as a pdf below.
Spring
Mud season doesn't last forever, and once it lifts, Southern Berkshire County opens up beautifully. Wildflowers line the trails at Bartholomew's Cobble in Sheffield and McLennan Reservation in Monterey. Monument Mountain's Squaw Peak loop is manageable for kids as young as five and rewards the climb with quartzite boulders and sweeping valley views. The Tanglewood grounds in Lenox are free to walk before the season opens — 524 acres of lawn and gardens, perfect for a picnic.
If you're staying at a rental property nearby, spring is ideal for slower mornings: the Great Barrington Farmers Market runs Saturdays starting in May, and the Great Barrington Public Library hosts free weekly story time year-round.
Summer
This is peak Berkshires. Benedict Pond at Beartown State Forest is one of the region's best-kept swimming holes — sandy, calm, and free. Lake Garfield in Monterey and Laurel Lake in Lee are quiet town beaches that rarely feel crowded. Jacob's Pillow in Becket offers free outdoor Peek Shows all summer long, and the Norman Rockwell Museum in Stockbridge is free for all visitors under 18.
Families renting in the area for a week will find the region particularly well-suited to longer stays — the kind where you hike one morning, swim in the afternoon, hit the farmers market on Saturday, and catch a free outdoor concert in the evening. Great Barrington, Stockbridge, and Lenox all anchor a network of activities that make a week feel full without being rushed.
Fall
Apple picking at Windy Hill Farm in Great Barrington, foliage hikes at Tyringham Cobble, hawk watching from Hurlburt's Hill at Bartholomew's Cobble — fall in Southern Berkshire County earns its reputation. The Berkshire Botanical Garden Harvest Festival over Columbus Day weekend draws families from across the region, and Stockbridge Main Street at Christmas (the weekend before Thanksgiving) is a community tradition unlike anything else in New England.
Fall weekend rentals in the area fill quickly — if you're planning a foliage trip, it's worth booking the itinerary and the lodging early. The back roads through Sheffield, Egremont, and New Marlborough are themselves worth the drive.
Winter
Butternut Basin and Bousquet Mountain offer accessible, unhurried skiing for young kids. Free sledding hills, ice skating at Pittsfield City Oval, and story times at the Great Barrington and Stockbridge libraries carry families through the quieter months. The Clark Art Institute in Williamstown is free for children year-round and warm enough to count as a full afternoon indoors.
Winter rentals in the Berkshires — particularly around Lenox and Great Barrington — offer a quieter version of the region that rewards slowing down. A fireplace, a puzzle, and a short drive to the slopes is a complete weekend.
[Download the Full Activity Guide →] Click this link to download the pdf
Photograph It While You're Here
Some of the most meaningful family portraits we make happen in the very places on this list. The grounds at The Mount, Edith Wharton's 1902 estate in Lenox, are among the most beautiful portrait settings in the Northeast — formal gardens, sweeping lawns, and architecture that photographs unlike anything else in the region. Family sessions at The Mount are by appointment, after hours, with a $130 donation to the estate for one hour on the grounds.
The open meadows near Tanglewood and Gould Meadows in Great Barrington offer a different kind of light — golden, wide, and unhurried — that works beautifully for families with younger children.
If you've been thinking about a portrait session while you're in the Berkshires, now is a good time to plan ahead.
[Reserve Your Family Portrait Session →] (Family Portrait Sessions)
These are some amazing captures!!!! Love how you did Eve’s eyes! Oh my heavens, Amy, you outdid yourself. These are SPECTACULAR. I've never had photos like this of my babies. There will certainly be prints! Seriously, I am in happy tears over how lovely these are. Thank you!!!!
I have known Amy since she was in a photography class in our high school together. She is not only an amazing person to work with but she also has captured some of the most memorable & precious moments of our life. She has been the main photographer at our wedding, taken our family Christmas photos, a 1st birthday photoshoot, and has also done a newborn photoshoot for us at the last moment. I am looking forward to capturing more moments in the future with our favorite photographer, Amy!
Incredible service! Amy is so patient, accommodating, and VERY skillful! She's awesome at what she does. We are beyond happy on how our maternity and newborn pictures came out!! We are definitely going to be hiring her for special occasions, yearly shoots, and business photos. Thank you so much Amy for your hard work, your passion truly shows!
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