Looking for New England charm with history and mountain beauty? Head to Windsor, Vermont! Known as the Birthplace of Vermont, this quaint town blends colonial heritage, scenic landscapes, and artisan culture. Whether you're strolling covered bridges or sipping local spirits, Windsor offers a peaceful and authentic Vermont escape.
🌤 When I like to visit
The best time to visit Windsor is during autumn (late September to mid-October) for spectacular foliage or summer (June–August) for outdoor activities and festivals. Winter brings cozy charm and snow-covered scenery, while spring sees maple tapping and quiet trails.
🗺 My tips for getting There
- By Car: Located along I-91 and U.S. Route 5, Windsor is about 2.5 hours from Boston and 1 hour from Montpelier.
- By Air: The nearest airport is Lebanon Municipal Airport (LEB), 30 minutes away, or Burlington International Airport (BTV), about 1.5 hours away.
- By Train: Amtrak’s Vermonter line stops at Windsor-Mt. Ascutney Station, with service between Washington, D.C. and northern Vermont.
🏬 Where I like to stay
- The Snapdragon Inn – Elegant boutique inn in a historic home with modern touches and garden views.
- The Windsor Mansion Inn – Grand hilltop inn with antique décor, breakfast service, and sweeping valley views.
- Climb Every Mountain Farmstay – Unique rustic lodging with farm animals and mountain tranquility nearby.
Top Attractions
1. Walk Through History (and Two States) on the Cornish-Windsor Covered Bridge
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"Walk or drive across one of the longest covered bridges in the U.S., connecting Vermont and New Hampshire."
Location: Windsor, VT
Recommended For: History lovers, photographers, scenic drive enthusiasts, couples, and covered bridge seekers.
What I Love: ♥ "There’s something magical about driving through the longest wooden covered bridge in the country—timbers creak, the river glimmers below, and history hums all around."
- Visit the iconic Cornish-Windsor Covered Bridge, the longest wooden covered bridge in the United States at approximately 449 feet in length.
- Walk or drive across this historic 1866 structure that connects Vermont and New Hampshire across the Connecticut River.
- Explore the area’s heritage, knowing this is the third bridge built at this scenic site—the first dating back to 1796.
Cost: Free to access and cross by foot or car.
Best time to visit: Fall for peak foliage views or spring for peaceful river scenes and fewer crowds.
Local tips: Stop on the Windsor side for photos and stroll the nearby village shops. Morning light casts beautifully on the bridge for pictures.
How to Get to Cornish-Windsor Covered Bridge: From I-91, take Exit 9 for VT-131 E toward Windsor. Continue through downtown Windsor to the bridge entrance. New Hampshire visitors can access it from NH Route 12A in Cornish.
Address: Windsor, VT
2. Raise a Pint and Toast Local Flavor at Harpoon Brewery
Location: Windsor, VT
Recommended For: Craft beer lovers, road trippers, foodies, and anyone seeking a fun and flavorful Vermont brewery stop.
What I Love: ♥ "It’s more than a brewery—it’s a riverside hangout with cold pints, bold flavors, and a story that started with three friends and a dream back in ‘86."
- Visit Harpoon’s second brewery location in scenic Windsor, where the Riverbend Taps & Beer Garden delivers flavor and community vibes.
- Sip on rotating selections of Harpoon beers, UFO series brews, seasonal ciders, and refreshing seltzers—all fresh from the source.
- Pair your pint with delicious pub fare like soft pretzels, hearty sandwiches, and beer-friendly snacks served in a relaxed, rustic space.
Cost: Entry is free; beer and food are priced individually. Flights available for sampling.
Best time to visit: Weekends for a lively crowd and full beer menu; weekdays for a quieter experience and personal service.
Local tips: Try a flight to sample both classic and seasonal brews. Don’t miss the gift shop—it’s packed with exclusive merch and take-home brews.
How to Get to Harpoon Brewery Windsor: From I-91, take Exit 9 for VT-131 W toward Windsor. Follow signs to Ruth Carney Drive; the brewery is near the Connecticut River, just past the American Precision Museum.
Address: 336 Ruth Carney Drive, Windsor, VT 05089
Phone: 802-674-5491
3. Hike to Enjoy Views from Majestic Mount Ascutney
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"Hike or drive to panoramic views from this iconic Southern Vermont mountain."
Location: Windsor, VT
Recommended For: Hikers, nature photographers, campers, hang gliders, and history-loving adventurers.
What I Love: ♥ "The trails, the views, the summit tower—it’s all the Vermont wilderness at its finest. There’s a stillness up here that makes you breathe a little deeper."
- Hike over a dozen miles of scenic trails from four different trailheads, offering a variety of terrain and difficulty levels.
- Discover remnants of historic logging camps, early homesteads, and stone quarries scattered along the trails.
- Climb to the summit and ascend the observation tower for breathtaking views of the Connecticut River Valley.
- Experience thrilling hang gliding launches or settle in for a peaceful night of camping under the stars.
Cost: Day use fees may apply; camping fees vary by site and season.
Best time to visit: Late spring through fall for hiking and views; fall offers spectacular foliage and cooler temps.
Local tips: The summit road is seasonal—check weather and access ahead. Bring layers and water for summit hikes, and don’t miss sunset from the tower.
How to Get to Mount Ascutney State Park: From I-91, take Exit 8 and follow VT-131 W. Turn left on Back Mountain Road and follow signs to the park entrance.
Address: 1826 Back Mountain Rd, Windsor, VT 05089
Phone: 802-674-2060
4. Paddle, Wander, and Reflect with Great River Outfitters and Path of Life Garden
Location: Windsor, VT
Recommended For: Outdoor adventurers, families, nature lovers, spiritual seekers, and campers looking for something unique.
What I Love: ♥ "One part peaceful garden walk, one part riverside adventure—this place lets you paddle, wander, reflect, and even sleep under the stars. It’s Vermont magic at its best."
- Adventure with Great River Outfitters, offering year-round outdoor excursions for all skill levels—from paddling the Connecticut River to winter snowshoeing and dog sledding.
- Stroll through the serene, Japanese-inspired Path of Life Garden, a symbolic landscape representing the journey of life across more than a dozen acres.
- Wander along peaceful walking trails and discover art installations, natural elements, and quiet spaces for reflection.
- Camp overnight in deluxe tents nestled within the garden for a one-of-a-kind glamping experience in harmony with nature.
Cost: Admission varies by activity. Garden entry and outdoor excursions have separate fees; camping rates available online.
Best time to visit: Spring through fall for full access to garden paths, paddling trips, and overnight stays. Winter activities available during snow season.
Local tips: Bring comfortable shoes and a camera. Combine a garden walk with an afternoon paddle for the ultimate day outdoors. Book camping in advance—spots fill up quickly in summer!
How to Get to Great River Outfitters and Path of Life Garden: From I-91, take Exit 9 and head toward Windsor. Follow signs to Artisans Park; both attractions are located next to Harpoon Brewery and other local destinations on Park Rd.
Address: 36 Park Rd, Windsor, VT 05089
Phone: 802-674-9933
5. Marvel at the Machines That Built America at the American Precision Museum
Location: Windsor, VT
Recommended For: History buffs, engineers, educators, makers, families, and anyone curious about how machines shaped modern life.
What I Love: ♥ "It’s where gears, ingenuity, and American history come together—each machine telling a story of innovation, industry, and precision craftsmanship."
- Explore the country’s largest collection of historically significant machine tools, showcasing the evolution of mechanical engineering.
- Visit the original 1846 Robbins and Lawrence Armory—a National Historic Landmark and birthplace of precision manufacturing in America.
- Learn about the people behind the machines through engaging exhibits that highlight both the tools and the lives of those who used them.
Cost: Admission prices vary; discounts available for students, seniors, and families. Children under a certain age may enter free—check the website for current rates.
Best time to visit: From Memorial Day weekend to the end of October, when the museum is open daily from 10:00 AM to 5:00 PM.
Local tips: Pair your visit with a stop at the nearby Harpoon Brewery or Great River Outfitters. Allow at least an hour for a full walkthrough—there’s a lot to see and learn!
How to Get to the American Precision Museum: From I-91, take Exit 9 and follow VT-131 W toward Windsor. Turn right onto Main Street; the museum is just past the bridge on your right.
Address: 196 Main St, Windsor, VT 05089
Phone: 802-674-5781
6. Step Into Revolutionary History at the Old Constitution House
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"Visit the birthplace of Vermont’s constitution, now a museum of state history."
Location: Windsor, VT
Recommended For: History enthusiasts, heritage travelers, educators, students, and anyone interested in early American democracy.
What I Love: ♥ "It’s humbling to stand in the very room where Vermont boldly outlawed slavery and expanded voting rights—this quiet house helped shape a more just America."
- Visit the “Birthplace of Vermont,” where delegates gathered in 1777 to draft the groundbreaking Vermont Constitution.
- Learn how this forward-thinking document was the first in America to prohibit slavery, allow non-landowning men to vote, and establish public education.
- Explore rooms restored to 18th-century detail and gain insight into the bold ideas that defined Vermont’s early independence.
- Connect to broader stories of freedom and justice on the Vermont African American Heritage Trail.
Cost: Modest admission fee; discounts available for seniors and children. Check the official site for current pricing.
Best time to visit: Saturdays and Sundays from late May through mid-October, when the site is open to the public for guided and self-paced tours.
Local tips: Combine your visit with stops at nearby historic sites or the American Precision Museum. The gift shop features great local books and souvenirs.
How to Get to the Old Constitution House: From I-91, take Exit 9 and head east toward downtown Windsor. The site is located at the southern end of Main Street, in the heart of town.
Address: 16 Main St, Windsor, VT 05089
Phone: 802-674-6628
7. Admire Timeless Beauty and Community Spirit at Old South Church
Location: Windsor, VT
Recommended For: History enthusiasts, architecture admirers, heritage travelers, spiritual seekers, and fans of early American design.
What I Love: ♥ "Timeless white clapboards, a rich spiritual history, and Asher Benjamin’s classic design—this church feels like a living thread woven into Windsor’s founding story."
- Visit the Old South Church, founded in 1768 and still serving the community more than 250 years later.
- Admire the Asher Benjamin-designed structure built in 1798, with its original exterior nearly untouched except for a 1920 portico addition.
- Reflect on the deep connection between the church and Windsor itself—both growing together since the town’s charter in 1761.
- Learn about its affiliation with the United Church of Christ and its longstanding role in shaping the town’s identity.
Cost: Free to visit; services and events open to the public. Donations welcome to support preservation efforts.
Best time to visit: Sunday mornings for worship, or during community and historical events for guided access and insight.
Local tips: Take time to appreciate the church’s setting along Main Street—perfect for photos and close to other historic Windsor landmarks.
How to Get to the Old South Church: From I-91, take Exit 9 and head into Windsor via VT-131 E. Continue on Main Street; the church is located near the heart of town, just north of the Constitution House.
Address: 146 Main St, Windsor, VT 05089
Phone: 802-674-5087
Where to Eat
8. If You Love Rustic Charm, Unwind at The Windsor Station Restaurant and Barroom
Location: Windsor, VT
Recommended For: Foodies, history buffs, date nights, craft cocktail fans, and anyone seeking a unique Vermont dining experience.
What I Love: ♥ "Dinner in a restored train station? It’s cozy, nostalgic, and just plain cool—especially when there’s live music and local craft beer on tap."
- Dine in a historic 19th-century train station, lovingly preserved with original architectural details and loads of small-town charm.
- Enjoy locally sourced Vermont dishes, wines, creative cocktails, and regional craft beers in a whimsical, welcoming setting.
- Unwind with live music on select evenings while sipping something special from the barroom.
Cost: Moderate; entrées typically range from $18–$35. Cocktails and desserts priced separately.
Best time to visit: Evenings Wednesday through Sunday; arrive early for a table on live music nights or make a reservation in advance.
Local tips: Sit by the old station windows for the best ambiance. Ask about the seasonal specials—they’re a local favorite for a reason.
How to Get to Windsor Station Restaurant: From I-91, take Exit 9 and head into downtown Windsor via VT-131 E. Turn onto Depot Avenue—the restaurant is located just steps from the rail tracks in the old station building.
Address: 26 Depot Ave, Windsor, VT 05089
Phone: 802-674-4180
Local Events
- Windsor Farmers Market (June–October) – Weekly event with fresh produce, local crafts, and live music.
- Harpoon Octoberfest (September) – Annual fall bash at Harpoon Brewery with food, beer, and live bands.
- Windsor Heritage Days (Summer) – Celebrate local history with reenactments, tours, and community fun.
Day Trips Within 30 Minutes of Windsor, Vermont
- Woodstock (20–25 min) – Stroll village streets, visit Billings Farm & Museum, or hike to Mount Tom’s summit.
- Hartland (15–20 min) – Explore forest trails, visit artisan studios, or enjoy peaceful countryside drives.
- Norwich (25–30 min) – Browse King Arthur Baking’s campus, shop local markets, or walk through charming village streets.
- Quechee (20–25 min) – Marvel at Quechee Gorge, visit the Vermont Institute of Natural Science, or shop glassblowers and craftspeople.
- Claremont, NH (10–15 min) – Walk along the Sugar River, visit historic mills, or shop downtown cafés and galleries.
- White River Junction (25–30 min) – Explore local art spaces, see a play at Northern Stage, or enjoy eclectic dining and bookshops.
- Springfield (20–25 min) – Visit the Eureka Schoolhouse, explore trails, or enjoy riverside parks and quiet neighborhoods.
- Plainfield, NH (25–30 min) – Visit the Saint-Gaudens National Historical Park, walk scenic roads, or tour covered bridges.
- Brownsville (15–20 min) – Hike Ascutney trails, explore small inns and farms, or take in mountain and valley views.
FAQ
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Where is Windsor located?
- The town of Windsor is in the picturesque state of Vermont, benefiting from one of New England’s most beautiful locations.
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What natural features surround Windsor?
- Situated by the Connecticut River under the scenic Mount Ascutney, Windsor is a place where natural beauty meets history.
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What attractions bring visitors to Windsor?
- Visitors are drawn to Windsor for its unique shopping experiences, charming downtown district, and outdoor recreation opportunities.
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What historic attractions can be found in Windsor?
- Windsor boasts a quaint Historic District full of architectural history, making it one of the largest in the state.
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What makes Windsor special for artisans and craftsmanship?
- Windsor is home to many artisans whose work can be seen throughout the town.
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What unique bridge can visitors see in Windsor?
- Windsor is home to America’s longest two-span covered bridge, a must-see landmark.
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