Vermont’s charm doesn’t shout — it whispers. It’s in the maple-scented breeze drifting through its green valleys, the clapboard houses lined with flower boxes, and the gentle hum of a main street bakery serving fresh cider donuts. While larger cities like Burlington have their allure, there are beautiful small towns to visit in Vermont that define its soul — a blend of timeless charm, outdoor adventure, and close-knit community life.
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Best towns to Visit in Vermont – Best Places to Visit in Vermont
If you’re planning a New England getaway, these best towns to visit in Vermont deserve a spot on your itinerary. From the postcard-perfect streets of Woodstock to the breathtaking mountain views of Stowe, each town tells a unique story — one of craftsmanship, nature, and genuine Vermont warmth.
This guide covers 10 of the best towns to visit in Vermont, complete with why to go, what to do (and why it’s worth doing), tours & attractions, and mid-budget places to stay. Whether you’re chasing fall foliage, cozy winter vibes, or summer festivals, these are the best places to visit in Vermont all year round.
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Stowe – Vermont’s Quintessential Mountain Village
Often called “The Ski Capital of the East,” Stowe offers far more than snow. Nestled beneath Mount Mansfield, Vermont’s highest peak, Stowe perfectly balances outdoor adventure with small-town elegance. It’s scenic, walkable, and equally enjoyable in summer and fall — making it one of the best Vermont towns to visit throughout the year.
Things to Do
- Ride the Stowe Recreation Path – A 5.3-mile paved trail weaving through farms, rivers, and bridges. Perfect for cycling or a morning walk to soak up the scenery.
- Take the Gondola SkyRide – The panoramic views of Mount Mansfield are jaw-dropping, especially during fall foliage.
- Explore Main Street – Charming boutiques, art galleries, and cozy cafés make downtown Stowe feel straight out of a Hallmark movie.
- Visit the Trapp Family Lodge – Yes, those Von Trapps from “The Sound of Music.” The Austrian-inspired lodge offers trails, a brewery, and historical charm.
Tours & Attractions – Book a guided hiking tour or brewery tasting experience. In winter, ski lessons at Stowe Mountain Resort are excellent for beginners.
Where to Stay – Green Mountain Inn – A classic, historic inn right in the heart of Stowe with traditional Vermont decor, a cozy tavern, and easy access to all attractions.
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Woodstock – A Storybook New England Village
If you could only visit one Vermont town that captures New England’s idyllic essence, it would be Woodstock. It’s known for covered bridges, an inviting village green, and walkable streets lined with heritage buildings.
Things to Do
- Visit Billings Farm & Museum – Learn about Vermont’s agricultural roots in this interactive, working farm experience.
- Wander the Village Green – The beating heart of Woodstock, perfect for people-watching or simply taking in the historic beauty.
- Middle Covered Bridge – A quintessential Vermont landmark and photo spot.
- Hike Mount Tom Trail – Offers the best panoramic view of Woodstock’s picturesque landscape.
Tours & Attractions – The Marsh-Billings-Rockefeller National Historical Park offers guided tours blending conservation, art, and history.
Where to Stay – The Shire Woodstock – Riverside rooms, scenic views, and easy walking distance to downtown. Excellent mix of comfort and affordability.
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Manchester – Chic Shopping Meets Mountain Air
Set at the base of Mount Equinox, Manchester blends rural sophistication with outdoor charm. It’s a great mix of designer outlets, farm-to-table dining, and mountain adventure — one of the best places to visit in Vermont for a balanced weekend.
Things to Do
- Hildene, The Lincoln Family Home – Explore the historic estate of Abraham Lincoln’s son, surrounded by gardens and rolling hills.
- Shop & Stroll – From Orvis flagship stores to locally owned boutiques, Manchester’s shopping is among the best in New England.
- Drive Skyline Drive – The road to the summit of Mount Equinox offers breathtaking views of the surrounding valley.
- Visit Northshire Bookstore – One of the most loved independent bookstores in the U.S.
Tours & Attractions – Book a guided nature walk through Equinox Preservation Trust or a cheese-tasting tour with local dairies.
Where to Stay – The Manchester View – Classic mountain inn ambiance with charming rooms, many featuring fireplaces and private decks.
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Shelburne – Lakeside Culture and Craftsmanship
Just south of Burlington, Shelburne blends scenic lakeside living with cultural depth. It’s a gem for art lovers and families alike. If you want a mix of the arts and waterfront strolling, Shelburne is a top pick.
Things to Do
- Shelburne Museum – A sprawling, open-air museum showcasing American art, architecture, and design. Ideal for a half-day of cultural immersion.
- Shelburne Farms – A working farm where you can tour the barns, taste cheeses, and enjoy walking trails with Lake Champlain views.
- Lake Champlain Access – Kayaking, sailing, or simply watching sunset from the docks.
Tours & Attractions – Book a farm tour at Shelburne Farms or attend a seasonal wine and cheese tasting event.
Where to Stay – T-Bird Motor Inn – A clean, affordable, and conveniently located stay just minutes from the museum and farms.
Waitsfield & Warren – The Soul of the Mad River Valley
Tucked into the Mad River Valley, these sister towns define rural Vermont living. Expect rolling hills, local farmers’ markets, and a thriving art scene. It’s perfect if you want rural scenes, artisan food, and outdoor recreation without the scale of larger resorts.
Things to Do
- Mad River Glen Ski Area – A cooperative-run ski resort with an old-school vibe and incredible terrain.
- Visit Local Farms & Breweries – Sample the true flavors of Vermont through cider, cheese, and maple syrup tours.
- Swim at Warren Falls – One of the most beautiful natural swimming holes in New England.
- Drive Route 100 – Vermont’s most scenic highway passes right through the valley.
Tours & Attractions – Book a guided snowshoe or mountain bike tour, depending on the season.
Where to Stay – The Warren Lodge – Rustic yet modern accommodations nestled by the river. Great value for its comfort and location.
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Middlebury – College Town with Small-Town Warmth
Middlebury combines academic energy with natural charm. Home to Middlebury College, it’s known for its scenic downtown, artistic events, and historic architecture. It’s quieter than the big tourist hubs but full of cafés, galleries, and access to outdoor pursuits.
Things to Do
- Explore Middlebury College Museum of Art – Compact but impressive, reflecting the intellectual spirit of the town.
- Visit Otter Creek Brewing – Sample some of Vermont’s best craft beers in a relaxed environment.
- Walk the Trail Around Middlebury (TAM) – Offers serene views of forests, rivers, and farmlands.
- See the Covered Bridges – The Pulp Mill Bridge is one of Vermont’s oldest.
Tours & Attractions – Enjoy a guided brewery tour or check local schedules for campus performances open to the public.
Where to Stay – Swift House Inn – A historic 19th-century home turned charming inn with a top-rated breakfast and cozy rooms.
Brattleboro – Bohemian and Artsy by the River
Brattleboro is situated along the Connecticut River and boasts a creative spirit unlike anywhere else in Vermont. It’s a hub for artists, musicians, and food lovers. It is perfect for travelers who love local music, bookstores, and community events.
Things to Do
- Explore the Brattleboro Farmers’ Market – Fresh produce, crafts, and live music every weekend.
- Catch a Show at Latchis Theatre – A restored Art Deco cinema that doubles as a performance venue.
- Visit the Brattleboro Museum & Art Center – Contemporary exhibits and local artists’ showcases.
- Stroll Downtown – Quirky boutiques, independent coffee shops, and bookshops define its atmosphere.
Tours & Attractions – Join a walking food tour or attend the Strolling of the Heifers Parade, a fun local event celebrating farm life.
Where to Stay – Latchis Hotel – Vintage charm in the heart of downtown, housed in the same building as the historic theatre.
Bennington – History and Heritage in the Green Mountains
Bennington is where Vermont’s Revolutionary War heritage meets small-town tranquility. It’s ideal for history buffs and antique lovers.
Things to Do
- Bennington Battle Monument – The tallest structure in Vermont, with panoramic views of three states.
- Bennington Museum – Home to folk art and the works of Grandma Moses.
- Covered Bridges of Bennington – Visit three iconic bridges within minutes of each other.
- Downtown Shopping – Filled with antique shops and local bakeries.
Tours & Attractions – Take a historical walking tour or visit the Old First Church and cemetery for a touch of colonial history.
Where to Stay – Paradise Inn – Centrally located, with clean, comfortable rooms and a seasonal outdoor pool.
Montpelier – The Smallest Capital City in America
Montpelier might be the nation’s smallest capital, but it has plenty of personality. Compact, charming, and lively — it’s great for history lovers and food enthusiasts.
Things to Do
- Vermont State House – Tour the beautifully preserved Greek Revival building.
- Explore Local Cafés & Shops – Everything is within walking distance; stop by Birchgrove Baking for pastries.
- Visit the Vermont History Museum – Learn how the state’s story shaped the region.
- Hike Hubbard Park Tower – Offers sweeping views of the city.
Tours & Attractions – Book a guided State House tour or attend a seasonal festival, such as the Green Mountain Film Festival.
Where to Stay – Capitol Plaza Hotel – Elegant yet affordable stay in downtown Montpelier, perfect for exploring on foot.
Grafton – A Step Back in Time
Grafton feels untouched by time — one of the most beautiful small towns to visit in Vermont. It’s quiet, authentic, and deeply tied to Vermont’s heritage.
Things to Do
- Visit the Grafton Village Cheese Company – Famous for handcrafted cheeses made on-site.
- Wander the Village Center – Restored 19th-century buildings and unspoiled scenery.
- Hike the Grafton Trails – Enjoy peaceful nature paths suitable for all skill levels.
- Explore Local Artisans – The Grafton Forge (blacksmith) and local galleries give insight into rural craftsmanship.
Tours & Attractions – Book a guided snowshoe tour in winter or attend the annual Grafton Nature Festival.
Where to Stay – The Grafton Inn – A historic inn dating back to 1801, beautifully preserved, offering genuine Vermont hospitality.
Useful Travel Tips for Visiting the Best Vermont Towns
- Best Time to Visit:
- Fall (Sept–Oct): Peak foliage, vibrant festivals.
- Winter (Dec–Mar): Ski season and cozy village vibes.
- Summer (Jun–Aug): Warm weather, outdoor concerts, and lakes.
- Driving Routes:
- Route 100 is Vermont’s most scenic drive, connecting many of these small towns.
- Route 7 covers the western part with easy access to Bennington, Manchester, and Middlebury.
- Dining Tips:
- Always try local maple syrup, cheddar, and cider.
- Farm-to-table restaurants are everywhere — they’re not a trend here, they’re a way of life.
- Budget Tip: Travel midweek or in late spring for better hotel rates and smaller crowds.
- Local Etiquette: Vermonters are known for their friendly nature and a strong emphasis on sustainability — they often use reusable bottles and prioritize shopping locally whenever possible.
FAQs – Small towns to Visit in Vermont – Vermont’s Timeless Allure
Q: What are the best towns to visit in Vermont for fall foliage?
A: Stowe, Woodstock, and Waitsfield top the list — they have scenic drives, mountain views, and picture-perfect maple groves.
Q: Which Vermont towns are best for winter vacations?
A: Stowe and Waitsfield (Mad River Valley) are best for skiing and snowboarding; Grafton and Woodstock are ideal for cozy cabin stays.
Q: What are some lesser-known small towns to visit in Vermont?
A: Grafton, Waitsfield, and Warren are quieter but equally beautiful alternatives to the more touristy hubs.
Q: Can you visit multiple Vermont towns in one trip?
A: Absolutely — most are within 1–2 hours’ drive. A 5–7-day road trip easily covers 5–6 of these best Vermont towns.
Some Itinerary Examples – Small Towns to Visit in Vermont – Best Places to Visit in Vermont
A relaxed 5-day Vermont slice (Great for first-timers)
- Day 1: Arrive Burlington → Shelburne Museum and waterfront → overnight Burlington/Shelburne.
- Day 2: Drive to Stowe → explore town and trails → overnight Stowe (Green Mountain Inn).
- Day 3: Stowe to Waitsfield (Mad River Valley) → afternoon farm visit or brewery → overnight Waitsfield.
- Day 4: Mad River Valley to Woodstock → stroll green and Billings Farm → overnight Woodstock.
- Day 5: Drive through Manchester (lunch and shopping) and head home or continue to Bennington.
A foliage-focused 7-day loop
Route: Burlington → Stowe → Waterbury → Mad River Valley → Woodstock → Manchester → Grafton → Burlington. Mix hikes, leaf drives (Route 100), and small museums. Be sure to pre-book lodging for peak times, such as fall tours or festive seasons.
Food + drink highlights you’ll want to try
- Maple syrup tastings and farm stands — seasonal musts.
- Local cheeses and creameries — pair them with cider or New England ales.
- Vermont breweries and cideries — small tasting rooms and strong local pride. Food & Wine and travel pieces celebrate Vermont’s growing fermentation scene.
Vermont’s small towns remind travelers what simplicity and community feel like. Each town — whether it’s Stowe’s alpine charm, Woodstock’s historic beauty, or Grafton’s frozen-in-time tranquility — captures a piece of what makes New England magical.
If you seek authenticity, connection, and slow travel, these are undeniably the best towns to visit in Vermont. Drive the backroads, stay in family-run inns, eat local, and take your time — because in Vermont, that’s exactly what you’re meant to do.
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