Things to Do in Windsor, Vermont
What to See, Do, and Eat On Your Trip
Windsor, a hamlet of 3,600 people along the Connecticut River, is famous as “the birthplace of Vermont,” where the state’s constitution was signed in 1777. Compared to the picturesque tourist mecca of nearby Woodstock, Windsor often gets overlooked. That’s a shame, given the town’s rich history as a bustling industrial hub from which products, machinery and new manufacturing techniques once spread worldwide.
While Windsor is more sedate than it was a century ago, there’s still plenty to see and do there, from the American Precision Museum, which explores the town’s role as the birthplace of manufacturing, to Artisans Park, which showcases Vermont’s leadership in producing craft foods, beverages and handmade wares. Windsor also offers easy access to year-round outdoor recreation, including skiing, hiking, biking and paddling.
Artisans Park
Visitors to Windsor can spend an entire afternoon shopping, dining and taking in live entertainment at this enclave of eight local businesses. Sample locally made craft beer, cider, tequila and root beer at the Harpoon Brewery Taproom and Beer Garden; craft and small-batch spirits, ciders and cocktails at the SILO Distillery barn and tasting room; and sweet and savory jams, preserves and marmalades at Blake Hill Preserves. Watch daily glassblowing and pottery-making demonstrations at Simon Pearce, then pick up some gift items for friends and family back home. Finally, get your blood pumping on an outdoor excursion with Great River Outfitters, which offers mountain bike rentals and self-guided float trips on the Connecticut River via canoes, kayaks, tubes and standup paddleboards.
Places to Visit in Windsor
Boston Dreams
This coffeehouse and bakery stands out in Windsor — not just because there aren’t many eateries downtown but because it’s also a Red Sox-themed sports gallery. The café offers creative hot and cold beverages including the Shamrock Mocha and Nutty Irishman, best enjoyed in nice weather on the outdoor patio. Try the baked goods, such as French toast muffins and raspberry cream cheese danishes, plus the pulled-pork panini, award-winning chili and lobster sliders. In keeping with Boston vernacular, the last should be pronounced “lobstah slidas.”
Windsor Diner
For old-school eats, the Windsor Diner is a classic, 1950s-era lunch counter serving breakfasts of eggs, omelettes, sausages and pancakes — and lunches of burgers, club sandwiches and tasty hand-cut fries. This train-car diner lives up to its motto, “Good food fast.”
Windsor Station Restaurant
This former Central Vermont Railway depot, which operated from 1901 until the mid-1960s, was converted into a railroad-themed restaurant in 1978. Today, it offers an impressive gourmet menu, from starters and small plates of blue crab cakes, fried calamari, bruschetta and saffron-citrus mussels to entrées of filet mignon, chicken piccata, blackened salmon and grilled sirloin chimichurri. The bar offers a solid selection of Vermont-made beers on tap. Reservations are strongly recommended.
Frazer’s Place
A small roadside snack bar and ice cream stand, Frazer’s Place punches well above its culinary class, serving up such unexpected eats as avocado-bacon Bennies for breakfast; pesto chicken melts for lunch; and shrimp scampi, beef tenderloin tips and General Tso’s chicken stir-fry for dinner. But it’s the frozen desserts that really take the cake: ice cream floats, sundaes and soft-serve ice cream — more commonly known in Vermont as creemees.
American Precision Museum
Windsor introduced the world to manufacturing decades before Henry Ford’s Model Ts rolled off the assembly line. This small but fascinating museum, located in a four-story former brick armory that’s now on the National Register of Historic Places, is a must-see for anyone who works with their hands or simply loves machinery and gadgets. And the museum isn’t only rooted in the past; it also demonstrates 21st-century, state-of-the-art machinery, including 3D printers and robots.
Cornish-Windsor Covered Bridge
No visit to Windsor is complete without a quick stop at the longest wooden bridge in the United States, built in 1866 for $9,000 to span the Connecticut River. The impressive structure is best photographed from the New Hampshire side facing Vermont, though as the historic sign on the east entrance warns, “Walk your horse or pay [a] two dollar fine.”
Path of Life Sculpture Garden
A serene and introspective outdoor experience can be found year-round at this 14-acre crafted landscape of unusual sculptures and walking paths along the Connecticut River. Allow plenty of time to lose yourself in the hedge maze, meander through the woods, and simply relax or picnic by the banks of the river.
Mount Ascutney State Park
One of Vermont’s oldest state parks encompasses the 3,144-foot Mount Ascutney, whose name comes from native Abenaki words meaning “mountain of the rocky summit.” The park offers more than 12 miles of hiking trails, with spectacular views of the Green and White mountains. Visitors seeking a less strenuous climb can drive up the 3.7-mile Mount Ascutney Parkway to an elevation of 2,800 feet, then hike the final mile to the summit. Visit for the day or camp overnight in a tent, RV or cabin.