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Rolling Berkshire hills, tree-canopied streets, and an arts scene that punches well above its size make summer in Williamstown, MA, pure gold. From mid-May farmers’ markets to leaf-tinged October hikes, this college town rewards slow exploring and wide-open curiosity. We’ve sketched out a seasonal roadmap—drawn from real weekends around town—to answer the perennial question of what to do in Williamstown to enjoy summer to the fullest.
Best Things to Do in Williamstown
Hike to the Summit of Mount Greylock
Massachusetts’ highest point rises just nine miles south of town on the summit of Mount Greylock, which is almost 3,500 feet. You can drive the scenic auto road (open May–October) or conquer the 6.6-mile Cheshire Harbor Trail on foot. Either route rewards you with 360-degree views of the Taconic, Adirondack, and Green Mountain ranges, plus a first-hand view of the local flora and fauna.
Explore the Clark Art Institute
World-class galleries meet rolling meadows at The Clark, where Degas sketches, Homer seascapes, and rotating contemporary exhibitions share space with glass-walled pavilions that frame grazing sheep. Pack a blanket for the free Wednesday evening concert series in July, and everyone should see the sunset in the reflecting pool at least once.
Wander the Williams College Museum of Art
Steps from Spring Street, WCMA trades ticket lines for curiosity-driven programming that anyone who appreciates art should see. You’ll find student-curated shows, modern photography, and an outdoor sculpture walk that leads past Chapin Library’s first-edition Shakespeare folios and the gothic arches of Thompson Chapel. Pop-up dance and improv sets often surprise weekday visitors on Sawyer Quad, so it is always fun to visit the museum through the summer months.
Trek the Pine Cobble Trail
If you’re up for a scenic but easily accessible hiking trail close to Williamstown, head to the Pine Cobble Trailhead on Pine Cobble Road. This trail winds 1.6 shady miles to a quartzite ledge overlooking the Hoosic Valley. No matter what time of year you visit the overlook, you get a new and unique view, so it’s always a treat. Sunrise in the summer paints Mount Greylock pink; sunset ignites autumn-tinged hilltops in late September for early leaf-peeping.
Book a Stay at Field Farm
Looking for a unique place to stay that will give you the best of Williamstown? Field Farm pairs mid-century modern rooms in a guesthouse with a 13-piece sculpture garden and 4.5 miles of flat meadow loops set in 300 acres of Massachusetts land. Bring local chèvre and strawberries from the farmers’ market and spread out beside the reflecting pond, and enjoy a farm-fresh breakfast every morning when you’re a guest.
Catch a Show at Williamstown Theatre Festival
For three weeks each July and August, Tony winners and Broadway up-and-comers transform the ’62 Center into a proving ground for new plays and star-studded revivals during the Williamstown Theatre Festival. Choose a matinee, then stick around for a maple-shaded talkback that often feels as enlightening as the performance itself.
Explore MASS MoCA in Nearby North Adams
A quick 6-mile drive east on the Mohawk Trail takes you to MASS MoCA, one of the largest contemporary-art museums in the country. Housed in a sprawling 19th-century mill complex, the venue fills 250,000 square feet with immersive installations, rotating exhibitions, and summer concert nights that spill into the courtyards. Grab a map at the entrance and wander from James Turrell’s light tunnels to the Sol LeWitt retrospective.
Best Festivals and Activities in Williamstown
Looking for local events to help you make the best of summer and immerse yourself with the local crowds? These community-driven events run from May to October and deliver the best activities in Williamstown, and many are free of charge and open to the public:
- Summer Sundays on Spring Street – Artisan vendors, live bands, and family crafts pop up downtown on select Sundays (June–August).
- Williamstown Farmers Market – Saturdays 9 a.m.–1 p.m. on Spring St.; stock up on maple cold brew, heirloom tomatoes, and local cheeses, May through October.
- Clark Summer Concert Series – Free global-music sets every Wednesday evening in July; picnics encouraged.
- Mount Greylock Auto Road Opening Day – Mid-May ribbon-cutting marks the start of summit drives and Bascom Lodge events.
Some of the Best Williamstown Restaurants
Refueling is simple, no matter what part of the city you are exploring. The area offers a full spread of Williamstown restaurants worth visiting when you’re on the lookout for the best food:
- Mezze Bistro & Bar – Seasonal Berkshire produce meets craft cocktails in a farmhouse-chic setting.
- Plates Mediterranean Bistro – Turkish-inspired flatbreads, house hummus, and sidewalk tables perfect for people-watching.
- The Log by Ramunto’s – Stone-fired NY-style pies, craft beer, and Williams memorabilia in a historic log cabin.
- Coyote Flaco – Roadside cantina serving smoky fajitas and top-shelf margaritas just south of campus.
- Spice Root – Modern Indian favorites (think Goan shrimp curry and garlic naan) plus a breezy patio for al fresco dinners on Spring Street.
- The Barn Kitchen & Bar – Elevated New England comfort fare—maple-glazed salmon, Berkshire pork chops, craft cocktails—served in the rustic-chic Williams Inn at the edge of campus.
The Ideal Pit-Stop for Quality Cannabis at Silver Therapeutics
Before you hike, gallery-hop, or set off exploring, stop at Silver Therapeutics to make sure your Williamstown experience is complete. Our shelves offer terpene-rich flower, concentrates, infused seltzers, edibles, vapes, and wellness products—you’ll have no trouble finding something to meet your preferences. Order ahead via the online menu for quick pickup, or pop in for tailored advice; our budtenders know the trail mileage to Pine Cobble and the curtain times at the ’62 Center by heart.
