Windsor, a hamlet of 3,600 people along the Connecticut River, is famous as "the birthplace of Vermont," a fact many people know from the signs along Interstate 91 rather than from actually visiting the town.
That's a shame, because Windsor deserves a closer look. While not as quaint or picturesque as the nearby tourist mecca of Woodstock, it's steeped in a rich, often forgotten history. Long before Chittenden County became the state's largest economic engine, Windsor was a bustling industrial hub from which products, machinery and manufacturing techniques spread worldwide. It's where the home sewing machine was invented and where, in the 19th century, rifles were first mass-produced for the U.S. and British governments.
Vermont's birthplace now faces many of the same challenges as the state's other aging towns. Its downtown hasn't fully recovered from the pandemic, and some of its historic structures look long in the tooth and in need of repair.
Chief among them is the Old Constitution House, once Elijah West's tavern. There, on July 8, 1777, Vermonters inked the country's first constitution to outlaw adult slavery, create a public school system and grant universal suffrage to men regardless of their income or property ownership — though women still couldn't vote until passage of the 19th Amendment to the U.S. Constitution.
Though it's a natural tourist draw, the Old Constitution House Museum has been shuttered since COVID-19 and sustained flood damage in 2023. It won't reopen until 2027, in time for the state constitution's 250th anniversary.
There's still much to see and do in Windsor. While the town is doubtlessly more sedate than it was a century ago, there are plenty of hopeful signs. A 25-unit apartment building is under construction downtown and slated to open next spring. And on the town's outskirts, a cluster of homegrown businesses is capitalizing on the Vermont brand of small-scale and organic agriculture, specialty foods, craft beverages, handmade art, and outdoor recreation.
What's happening in Windsor could be emblematic of the state as a whole. Here's an itinerary for diving into the town's past and present, three to six hours at a time.
Begin a visit by grabbing breakfast, brunch or lunch downtown. For traditional fare, the Windsor Diner on Route 4/Main Street is a classic, 1950s-era lunch counter serving breakfasts of eggs, omelettes, sausages and pancakes; and lunches of burgers, club sandwiches, BLTs and tasty hand-cut fries. It lives up to its motto, "Good food fast."
For quirkier fare, pop into Boston Dreams coffeehouse and sports gallery. Decked out in Red Sox décor and Fenway Park memorabilia, this café offers creative hot and cold beverages including the Shamrock Mocha and Nutty Irishman, best enjoyed on the outdoor patio. Try the delectable baked goods, such as French toast muffins and raspberry cream cheese danishes, plus pulled-pork paninis, award-winning chili and lobster sliders. The last should be pronounced "lobstah slidas."
Windsor doesn't have much of a shopping district, but Friends & Company, at 60 Main, warrants a visit. Gina Wenz, who's owned and operated the secondhand boutique for 50 years, is a font of information about Windsor. Once a turn-of-the-century bank, Wenz's store still houses its original vault, which she uses as a changing room.
"The aesthetics of it are spectacular, all brass and etched steel," she said. Years ago, Wenz displayed jewelry there, but few shoppers ventured inside. "People were too claustrophobic to go in and shop," she explained, "but no one has a problem going in there to strip."
From there, history buffs can poke around the Old South Church Cemetery on Main Street, one of Windsor's five historic graveyards dating back to the 1700s. Nearby is the old Windsor House, a former 19th-century hotel listed on the National Register of Historic Places, whose walls are lined with black-and-white photos, including one of president Theodore Roosevelt's Windsor visit.
If you seek a more comprehensive history lesson, the American Precision Museum just down Main Street is a must-see, especially for those who love tools, gadgets and machinery. As museum codirector Steve Dalessio noted, "Windsor is the birthplace of manufacturing."
That's no empty boast. A National Historic Landmark, the four-story former brick armory was built in 1846 by gunsmiths Nicanor Kendall and Richard Lawrence, who won a contract to manufacture 10,000 rifles for the U.S. government. For bulk production and battlefield efficiency, the guns needed interchangeable parts. Decades before Henry Ford's Model Ts rolled off the assembly line, Kendall and Lawrence figured out how to mechanize rifle manufacturing using precision machinery powered by a waterwheel in neighboring Mill Brook. Museum visitors can still see and operate the belt-driven mechanisms that snake throughout the building.
The American Precision Museum doesn't just dwell on the past, though. As Dalessio said, "We want to inspire a new generation ... that manufacturing has great future job potential. We want to feed that pipeline."
To that end, the museum houses and demonstrates state-of-the-art manufacturing equipment, including 3D printers, milling machines and "cobots," or collaborative robots that can work alongside humans. Its forthcoming $2.8 million expansion will create an education center and makerspace for kids, teens and students at the tech centers in Randolph and Springfield.
No visit to Windsor is complete without a photo op at the Cornish-Windsor covered bridge spanning the Connecticut River. Built in 1866 for $9,000, it's the longest wooden bridge in the U.S. and the longest two-span covered bridge in the world. Photos are best shot from the New Hampshire side — though, as the historic sign on the east entrance warns, "Walk your horses or pay [a] two dollar fine."
For an afternoon adventure, Artisans Park, a conclave of eight local businesses, offers one-stop shopping, dining, music, entertainment and exploration. There, visitors can discover craft beers, spirits, ciders and cannabis; take in handmade art; and enjoy outdoor recreation.
Sample beers, tequila and root beer at the Harpoon Brewery Taproom and Beer Garden, shop for beer-themed gifts, and grab a bite in the café. Reservations are strongly recommended on weekends, especially for outdoor patio seating. Alas, the brewery no longer offers guided tours, but Harpoon still hosts events such as live music Thursdays.
In another sign of Vermont's changing times, Harpoon offers customers a 10 percent discount coupon for nearby Stone Leaf Dispensary. Though cannabis products cannot yet be certified as organic, Stone Leaf champions an all-natural approach. All of its products, including edibles and vape cartridges, are solvent-free and made in a 100 percent solar-powered facility. Stone Leaf is also among the few Vermont dispensaries offering its flower both prepackaged and deli-style, with a counter scale and reusable jars.
"I've been to dispensaries up and down this side of the state," customer Cliff Roberge said during a recent visit, "and this my favorite, hands down."
Across the parking lot at Blake Hill Preserves, shoppers can sample and purchase sweet and savory preserves, jams and marmalades. Founded in 2009 by Vicky Allard and Joe Hanglin of Grafton as a home-based enterprise, Blake Hill Preserves has since grown into an award-winning business with products sold in more than 700 stores nationwide. According to manager Jane Hughes, the Windsor headquarters is about to break ground on an expansion that will double its retail and production capacity.
The company's latest accolade: a 2024 Good Food Award for its jalapeño-and-lime spicy chile jam. Also recommended for health-conscious consumers are its Naked Jams, sweetened with cocoa and fruit juices. The Naked chocolate sea salt, dairy-free with no added sugar, tastes downright decadent.
Just across a tree-lined lane is the SILO Distillery barn and tasting room, where visitors can sample and purchase craft and small-batch spirits, ciders and cocktails. On Sundays, stop in for Music & Marys — as in Bloody Marys — and on Fridays, check out SILO's live music series from 6 to 8 p.m.
Though Windsor birthed the concept of mass production, some items are best made by hand, especially the glassware, pottery and gifts at Simon Pearce. Artisans Park is home to the company's corporate headquarters, outlet store and pottery production facility, where visitors can browse the aisles, wander the catwalks and watch glassblowing demonstrations.
After loading up on food, spirits and gifts, it's time to enjoy the outdoors. Sandwiched between the brewery and distillery is Great River Outfitters, which offers self-guided trips on the Connecticut River via kayaks, canoes, rafts, standup paddleboards and inner tubes. Float times vary from two to five hours, depending on river conditions.
For land-based exploration, Great River has a rental fleet of fat-tire bikes, which beginner to intermediate cyclists can use to explore miles of woods and fields along the river.
A more serene and introspective outdoor experience can be found year-round in the Path of Life Garden, where guests wander the 14-acre crafted landscape of unusual sculptures and walking paths. Allow plenty of time to lose yourself in the hedge maze, meander through the woods or relax by the river. Camping is also available, though no dogs are allowed.
A hike to the 3,144-foot summit of Mount Ascutney, Windsor County's tallest peak, could easily consume three to six hours in Windsor on its own. Nearby Mount Ascutney State Park, among Vermont's oldest, has four trailheads with more than 12 miles of hiking and tent and RV sites and cabins for rent. For a less strenuous climb, drive the 3.7-mile Mount Ascutney Parkway to 2,800 feet, then hike the last mile to the summit for stunning views of the Green and White mountains.
Want to see Mount Ascutney without the elevation gain? Easily accessible from downtown Windsor is Lake Runnemede in Paradise Park. Popular among birders, the lake is the only known home on Earth of an extremely rare pondweed; hence, no swimming or boating is permitted. Come summer, the north dike is reportedly a good place to see white water lilies and the beavers that dive into and harvest them.
As the day draws to a close, grab dinner or appetizers at Windsor Station Restaurant at 26 Depot Avenue. The former Central Vermont Railway depot opened in 1901 and remained a fully operational station until the mid-1960s.
Converted into a railroad-themed restaurant in 1978, Windsor Station now 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 wide selection of Vermont-made draft beers. And the full menu is available there, in case you can't secure a reservation — "Usually, if you just walk in and get a table, you're lucky," one hostess warned.
For desserts, drop by Frazer's Place at 2066 Route 12. This small roadside snack bar and ice cream stand 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 take the cake: ice cream floats, sundaes and "soft-serve" ice cream. Frazer's can be excused for not using the term "creemee" — it must be the proximity to New Hampshire — given that the Reese's Peanut Butter Cup sundae alone is worth the trip. After a long day of steeping in Vermont's industrious history, go big before going home.