Keep Reading
There’s a spot in New England where Massachusetts, New York, and Vermont all touch, and that crossroads makes for one of the most eclectic and scenic weekend road trips you can plan. Silver Therapeutics’ Williamstown dispensary sits right at this tri-state border, offering a unique jumping-off point to experience the character of all three states in a single getaway. Fans of peak foliage, crisp fall flavors, or a patchwork of local culture will find this loop ideal for watching the borders blur and the views change nearly every mile.
Why the Tri-State Border Makes an Exceptional Road Trip
What sets this patch of the Berkshires apart is how quickly the landscape and culture shift. In under an hour, you can roll from the historic college town of Williamstown, MA, across scenic valleys into upstate New York, then cross over into the small towns and classic countryside of Vermont. Each state comes with its own set of autumn traditions, making every border a gateway to new fall favorites.
Top Things To Do Around Williamstown, MA
Williamstown itself is a destination for lovers of art, architecture, and small-town charm. Start at the Clark Art Institute for a wander among masterpieces and wooded trails, or visit the Williams College Museum of Art. In fall, stroll Spring Street for local cafes and shops, or time your visit during the Williamstown Farmers Market for fresh produce and baked goods.
Leaf-peeping is practically a rite of passage here; the roads outside of town wind through some of the Berkshires’ most vivid forests. Hop off Route 2 (known as the Mohawk Trail) for iconic views at the Western Gateway Heritage State Park.
Vermont Detour: Foliage, Farms, and Brewing
Crossing north, southern Vermont in the fall is postcard-perfect. Bennington, the first major town, has the old New England steeples and sprawling apple orchards you’d expect. Stop at apple farms like Terry’s Orchard or browse handmade goods in the historic downtown.
For those chasing foliage, drive Route 7 into Manchester for panoramic views and access to hiking trails like those on Mount Equinox. Vermont’s small-town breweries, such as Harvest Brewing, make for relaxed pit stops. Check their hours before visiting, as many close early outside of peak season.
New York’s Taconic Vistas and Autumn Flavors
Head west into New York, where the Taconic Mountains yield to farmland and wine country. The village of Chatham is a worthy detour for pumpkin patches, like Samascott Orchards, and a selection of cideries serving up classic fall sips. Further south, stroll the streets of Hudson, a hotspot for indie bookstores, bakeries, and antique shops curated with unmistakable Hudson Valley style.
If you’re traveling in October, some farm stops host harvest events, with hayrides, local food trucks, and live music tucked between the rows of pumpkins and bright leaves.
Planning Your Loop, and a Stop at Silver Therapeutics Williamstown
Because the drive between each state is so short, this trip works well for a two-day loop or a long fall weekend. Each leg is packed with roadside farm stands and places to stretch your legs among the maples. A shopping stop before heading home at Silver Therapeutics Recreational Dispensary in Williamstown offers a menu of cannabis products for adults 21+ with proper ID. It’s a convenient place to pause, browse, and plan the next leg of the journey, regardless of whether you begin or end your adventure at the tri-state crossroads.
This route offers a blend of culture, foliage, and seasonal fun, packing an impressive range of experiences into a single weekend road trip. The tri-state region’s mix of scenic drives, local flavor, and vibrant towns comes together for a travel loop that showcases the best of each state in a memorable fall journey.
