BWindsor, a village of 3,600 people on the Connecticut River, is known as the “Birthplace of Vermont” because it was here that the state constitution was signed in 1777. Windsor is often overlooked compared to the quaint tourist mecca of nearby Woodstock. That’s a shame, considering the town has a rich history as a bustling industrial center from which products, machinery and new manufacturing techniques were once distributed worldwide.
Windsor may be quieter than it was a century ago, but 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 the production of artisanal foods, beverages and handcrafted goods. Windsor also offers easy access to year-round outdoor recreation, including skiing, hiking, biking and paddling.
If you’re planning to visit Windsor, Vermont, here’s a suggested itinerary.
Note: Please check the websites for opening hours on the day you plan to visit.
Boston Dreams
This coffeehouse and bakery stands out in Windsor—not only because there aren’t many restaurants downtown, but because it’s also a Red Sox-themed sports gallery. The cafe offers creative hot and cold beverages like the Shamrock Mocha and Nutty Irishman, best enjoyed on the outdoor patio when the weather’s nice. Try the baked goods like French toast muffins and raspberry cream cheese danish, as well as the pulled pork panini, award-winning chili, and lobster sliders. According to Boston vernacular, the latter should be pronounced “lobstah slidas.”
7 State Road, Windsor
Windsor Diner
For old-school dining, the Windsor Diner is a classic 1950s diner that serves eggs, omelets, sausages and pancakes for breakfast – and burgers, club sandwiches and tasty hand-cut fries for lunch. This train car diner lives up to its motto of “good food, fast.”
135 Main Street, Windsor
American Precision Museum
Windsor introduced the world to manufacturing decades before Henry Ford’s Model T rolled off the assembly line. This small but fascinating museum, housed in a four-story brick former armory and now on the National Register of Historic Places, is a must-see for anyone who works with their hands or simply loves machines and equipment. And the museum isn’t just rooted in the past; it also showcases cutting-edge 21st-century machinery, including 3D printers and robots.
196 Main Street, Windsor
Cornish-Windsor Covered Bridge
No visit to Windsor would be complete without a quick stop at the longest wooden bridge in the United States, built across the Connecticut River in 1866 at a cost of $9,000. The impressive structure is best photographed from the New Hampshire side, which faces Vermont, although the historic sign at the east entrance warns, “Walk your horse or pay a two-dollar fine.”
Bridge St., Windsor
Craftsmen’s Park
Visitors to Windsor can spend an afternoon shopping, dining and enjoying live entertainment at this enclave of eight local businesses. Sample locally made craft beer, cider, tequila and root beer at Harpoon Brewery Taproom and Beer Garden; handcrafted and small-batch spirits, cider and cocktails at SILO Distillery’s barn and tasting room; and sweet and savory jams, preserves and marmalades at Blake Hill Preserves. Watch daily glassblowing and pottery demonstrations at Simon Pearce, then pick up a few gifts for friends and family back home. Finally, get your blood pumping with an outing with Great River Outfitters, which rents mountain bikes and offers self-guided float trips on the Connecticut River in canoes, kayaks, tubes and stand-up paddleboards.
71 Artisans Way, Windsor
Sculpture Garden “Path of Life”
This 35-acre, artfully landscaped area with unusual sculptures and walking trails along the Connecticut River offers a peaceful and contemplative outdoor experience year-round. Take plenty of time to get lost in the hedge maze, stroll through the forest, and simply relax or picnic on the river bank.
36 Park Rd., Windsor
Mount Ascutney State Park
One of Vermont’s oldest state parks includes 3,144-foot-tall Mount Ascutney, whose name comes from the native Abenaki words meaning “mountain of the rocky peak.” The park offers more than 12 miles of hiking trails with spectacular views of the Green and White Mountains. Visitors who prefer 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. Spend a day trip or stay overnight in a tent, RV or cabin.
1826 Back Mountain Rd., Windsor
Windsor Station Restaurant
In operation from 1901 to the mid-1960s, this former Central Vermont Railway railroad depot was converted into a railroad-themed restaurant in 1978. Today, it offers an impressive gourmet menu, from appetizers and small plates of blue crab cakes, fried calamari, bruschetta, and saffron citrus mussels to mains like filet mignon, chicken piccata, blackened salmon, and grilled sirloin chimichurri. The bar has a solid selection of Vermont-made beers on tap. Reservations are highly recommended.
26 Depot Ave., Windsor
Frazer’s Place
Frazer’s Place, a small roadside snack bar and ice cream shop, far exceeds its culinary standards, serving up such unexpected treats 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 the crowning glory is the frozen desserts: ice cream floats, sundaes, and soft serve ice cream—better known in Vermont as creemees.
2066 Route 5, Windsor
