If you're chasing New England charm, a little history, and gorgeous mountain scenery, I think you’ll love Windsor, Vermont as much as I do. I wandered into this town looking for peace—and found cobblestone streets, cozy bridges, and craft distilleries that made me linger. You’ll get a real taste of Vermont here, from artisan shops to quiet lakeside strolls. It’s the kind of place that gently pulls you in.
Best Time to Visit
I always try to make it here in the fall—between late September and mid-October. You won’t believe the color show across the hills. But if you visit in summer, you’ll find festivals, kayaking, and those warm, golden evenings that feel endless. I’ve even come in winter, just to slow down and enjoy the snow-covered calm. Spring’s quieter, but you’ll catch maple tapping season—and that’s a sweet experience you won’t forget.
How to Get There
- By Car: I usually drive up via I-91 or Route 5. It takes me about 2.5 hours from Boston or just an hour from Montpelier. It’s a beautiful drive either way.
- By Air: When I flew in, I used Lebanon Municipal (LEB)—it’s only 30 minutes out. If you’re okay with a longer ride, Burlington International (BTV) works too at about 1.5 hours.
- By Train: I took Amtrak’s Vermonter line once, and getting off at Windsor-Mt. Ascutney Station felt like stepping into a storybook. It’s a great option if you want to relax and skip the car.
Where to Stay
- The Snapdragon Inn – I stayed here once and couldn’t get over the blend of elegance and comfort. You’ll love the garden views and how close it is to everything.
- The Windsor Mansion Inn – This spot sits grandly on a hilltop. I woke up to valley views and antique charm—it’s perfect if you want something classic and quiet.
- Climb Every Mountain Farmstay – If you’re like me and crave something unique, this rustic farmstay hits the mark. You’ll meet friendly animals and breathe in nothing but mountain air.
Top Attractions in Windsor, Vermont
First: Walk Through History (and Two States) on the Cornish-Windsor Covered Bridge
Walk or drive across one of the longest covered bridges in the U.S., connecting Vermont and New Hampshire.
Second: Raise a Pint and Toast Local Flavor at Harpoon Brewery
Third: Hike to Enjoy Views from Majestic Mount Ascutney
Hike or drive to panoramic views from this iconic Southern Vermont mountain.
Fourth: Paddle, Wander, and Reflect with Great River Outfitters and Path of Life Garden
Fifth: Marvel at the Machines That Built America at the American Precision Museum
Sixth: Step Into Revolutionary History at the Old Constitution House
Visit the birthplace of Vermont’s constitution, now a museum of state history.
Seventh: Admire Timeless Beauty and Community Spirit at Old South Church
Eight: If You Love Rustic Charm, Unwind at The Windsor Station Restaurant and Barroom
Local Events
- Windsor Farmers Market (June–October) – The Windsor Farmers Market is a weekly event I never miss when I’m in town. It’s the perfect spot to grab fresh produce, browse local crafts, and enjoy live music while soaking up the town’s laid-back vibe.
- Harpoon Octoberfest (September) – Harpoon Octoberfest is one of those events that I look forward to every fall. It’s an annual bash at Harpoon Brewery, and the food, beer, and live bands make for an unforgettable day with friends and family.
- Windsor Heritage Days (Summer) – If you’re into history like I am, you’ll love Windsor Heritage Days. The reenactments, tours, and community fun really bring the town’s past to life, and I’ve had a blast learning more about Windsor’s rich history.
Day Trips Within 30 Minutes of Windsor, Vermont
- Woodstock (20–25 min) – Woodstock is a charming village with so much to offer. I love strolling through the village streets, visiting Billings Farm & Museum, and hiking up to Mount Tom’s summit for panoramic views of the area.
- Hartland (15–20 min) – Hartland is the perfect place for a peaceful getaway. I’ve spent a few afternoons exploring the forest trails, visiting artisan studios, and just enjoying the quiet, scenic countryside drives.
- Norwich (25–30 min) – Norwich is such a welcoming town. I’ve spent hours browsing King Arthur Baking’s campus, shopping at the local markets, and walking through the charming village streets. It’s a great place for foodies and shopaholics!
- Quechee (20–25 min) – I always enjoy a trip to Quechee. The gorge is breathtaking, and visiting the Vermont Institute of Natural Science or shopping for glassblown art adds to the fun. It’s one of those spots I keep coming back to.
- Claremont, NH (10–15 min) – Claremont is a lovely little town that I enjoy visiting. I always make time to walk along the Sugar River, explore the historic mills, and stop by the downtown cafés and galleries. It’s a relaxing day trip.
- White River Junction (25–30 min) – White River Junction has such a creative vibe. I love exploring the local art spaces, catching a play at Northern Stage, and enjoying eclectic dining and browsing through the unique bookshops.
- Springfield (20–25 min) – Springfield is perfect for a mix of outdoor and cultural activities. I’ve enjoyed visiting the Eureka Schoolhouse, exploring trails, and relaxing at riverside parks. It’s a great place for some downtime.
- Plainfield, NH (25–30 min) – Plainfield has some incredible scenery, and I always make a point to visit the Saint-Gaudens National Historical Park. Walking the scenic roads and touring the covered bridges is one of my favorite ways to spend a quiet afternoon.
- Brownsville (15–20 min) – Brownsville is a peaceful town where I love hiking the Ascutney trails, exploring small inns and farms, and enjoying the stunning mountain and valley views. It’s a great place to get away from it all.
FAQ
- Where is Windsor located?
- Windsor is a beautiful town located in Vermont, nestled on the western slope of the Wellsville Mountains and at the end of Box Elder Canyon. It’s one of the most picturesque spots in New England!
- What natural features surround Windsor?
- Windsor is beautifully situated by the Connecticut River, with Mount Ascutney serving as a stunning backdrop. The town is where natural beauty and history perfectly come together, making it an ideal place to visit for outdoor lovers like me.
- What attractions bring visitors to Windsor?
- Visitors flock to Windsor for its unique shopping experiences, charming downtown district, and opportunities for outdoor recreation. I always enjoy exploring the local shops and taking in the picturesque surroundings!
- What historic attractions can be found in Windsor?
- The Historic District in Windsor is full of architectural gems. It’s one of the largest in the state, and I love spending time wandering the streets, admiring the buildings, and learning about the town’s past.
- What makes Windsor special for artisans and craftsmanship?
- Windsor has a vibrant community of artisans whose work can be seen all over the town. From handcrafted goods to locally made art, I love seeing the town’s creativity come to life in its many galleries and shops.
- What unique bridge can visitors see in Windsor?
- Windsor is home to America’s longest two-span covered bridge, which is one of the town’s must-see landmarks. It’s not only beautiful but also rich in history!
Plan Your Trip
