10 Most Charming Small Towns in Vermont for a Fall Getaway

There’s something magical about Vermont’s small towns, especially in the fall! From classic covered bridges and white-steepled churches to vibrant farmers’ markets and cozy cafés, these villages feel like they were pulled straight from a postcard.

Whether you’re here for the fiery foliage, the winding country roads, or just a slower pace of life, you’ll find plenty of charming spots worth adding to your Vermont itinerary.

I’ve rounded up 10 of the most beautiful small towns in Vermont, from famous leaf-peeping destinations to hidden gems you might not have heard of. Each one has its own personality, but all are perfect for a fall getaway!

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Charming Small Towns in Vermont You Can’t Miss

1. Woodstock

Woodstock is one of Vermont’s most charming small towns, especially when the leaves turn shades of red, orange, and gold in the fall!

With its covered bridges, historic buildings, and cozy main street lined with cafés and boutiques, it’s the kind of place where you’ll want to slow down and soak it all in.

A fall weekend in Woodstock has plenty to offer, from crossing the postcard-perfect Middle Covered Bridge to taking in the views at Sleepy Hollow Farm, one of Vermont’s most photographed spots.

History lovers will enjoy visiting Billings Farm & Museum to learn about the area’s agricultural heritage and sample fresh maple syrup.

For outdoor adventures, head to Marsh-Billings-Rockefeller National Historical Park for scenic hiking trails or drive a few minutes to Quechee Gorge for dramatic views of Vermont’s “Little Grand Canyon.”

With so much to see and do, it’s easy to understand why this village is such a popular destination for leaf peeping. For even more ideas, check out this list of the best things to do in Woodstock in the fall!

2. Stowe

Stowe is one of Vermont’s most iconic destinations for fall foliage, and it’s easy to see why. With its white church steeple framed by colorful mountains, charming main street, and surrounding covered bridges, it feels like classic New England at its best.

There’s plenty to fill a weekend in this small mountain town. Start with a stroll along Stowe’s Main Street, where you’ll find cozy cafés, boutique shops, and art galleries.

For some outdoor adventure, consider hiking Stowe Pinnacle or driving the winding roads of Smugglers’ Notch, which offers some of the most stunning foliage views in the state!

You’ll also find plenty of things to do in Stowe in the fall beyond leaf peeping. Visit the Trapp Family Lodge for a taste of Austria in Vermont, bike the scenic Stowe Recreation Path, or explore local cideries and breweries.

If you have more time, my guide to 3 days in Stowe is packed with ideas for making the most of your visit!

3. Grafton

Tucked away in southern Vermont, Grafton feels like a step back in time. This tiny village is known for its beautifully restored 19th-century homes, quiet streets lined with maples, and a classic white steepled church at the center of town.

It’s one of Vermont’s oldest settlements and easily one of its most charming!

Take a stroll around the village to admire the historic architecture and stop by the Grafton Village Cheese Company for a taste of locally made cheddar.

The Grafton Inn, in operation since 1801, is a piece of living history and a lovely spot for lunch or a cozy overnight stay. Grafton Trails & Outdoor Center is a great spot for hiking or biking, surrounded by fall colors.

With its peaceful atmosphere and postcard-worthy scenery, Grafton is the kind of place that feels like a hidden gem, perfect for a quiet fall escape.

4. Manchester

Manchester feels like a classic Vermont town with a little extra polish. Surrounded by the Green Mountains, it’s packed with boutique shops, art galleries, and cute cafés that make it perfect for a relaxing fall getaway.

You can wander through the historic village center, visit Hildene (the Lincoln family estate) for incredible mountain views, or drive up to Mount Equinox for a foliage-filled panorama.

The town’s outlet stores and farmers’ markets are great for a little shopping, and there are plenty of cozy spots to grab a coffee or a farm-to-table meal.

Manchester is also one of the best places to stay in Vermont in the fall if you’re planning to explore southern Vermont. Its central location makes it easy to visit nearby towns like Dorset and Weston on scenic drives through some of the prettiest foliage in the state.

5. Montpelier

Montpelier might be Vermont’s capital, but it feels more like a small town than a bustling city. With its historic brick buildings, indie bookstores, and cafés lining the streets, it’s one of the most charming Vermont towns to visit in the fall.

You can start your day with a coffee and pastry downtown, then wander over to the gold-domed Vermont State House. For a taste of local life, don’t miss the farmers’ market or one of the town’s cozy restaurants serving up seasonal dishes.

If you’re into short hikes, Hubbard Park offers trails that lead to a stone observation tower with views over the town.

Montpelier is a great stop on a Vermont fall road trip, especially if you want a mix of small-town charm and a little culture.

6. Shelburne

Shelburne is just a few miles south of Burlington, making it a great stop if you’re exploring the Lake Champlain area in the fall.

With its peaceful setting and vibrant foliage, it’s easy to see why this village makes so many lists of the best small towns in Vermont!

One of the main draws here is Shelburne Museum, where you can wander through historic buildings and gardens surrounded by fall colors.

Shelburne Farms is another favorite, offering scenic walking trails, a beautiful historic inn, and plenty of chances to sample local cheese.

And since Burlington is so close, you can easily combine your visit with some of the best things to do in Burlington, like strolling the waterfront or grabbing a drink on Church Street.

7. Bennington

Bennington is one of southern Vermont’s most charming towns, with a mix of history, art, and classic New England scenery. It’s a great spot to explore in the fall, surrounded by rolling hills and dotted with covered bridges.

You can visit the Bennington Battle Monument, the tallest structure in Vermont, for sweeping views of the town and surrounding foliage. Downtown has a laid-back vibe with art galleries, antique shops, and plenty of cozy cafés for a midday break.

Don’t miss the Old First Church and nearby Bennington Cemetery, where poet Robert Frost is buried.

If you love scenic drives, the roads around Bennington are perfect for a relaxed afternoon of leaf peeping.

8. Waitsfield

Waitsfield is a small Vermont town in the heart of the Mad River Valley, surrounded by some of the state’s best fall foliage. With its laid-back vibe and postcard-worthy scenery, it’s one of the best small towns in Vermont for a quiet escape.

Spend some time exploring the historic covered bridges around town, like the iconic Waitsfield Covered Bridge, or browse local shops and art galleries. If you’re hungry, stop by one of the town’s farm-to-table restaurants or grab a cider donut from a nearby market.

This is also a great base for scenic drives through the Mad River Valley, with rolling hills and mountain views that are especially stunning in late September and early October.

9. Brattleboro

Creative, quirky, and full of character, Brattleboro has a personality all its own. This artsy southern Vermont town is known for its vibrant downtown, with indie bookstores, coffee shops, and galleries tucked into historic brick buildings.

It’s a fun spot for wandering on a crisp fall day. You can browse the Brattleboro Farmers’ Market, check out local art studios, or grab a cider at one of the cozy pubs in town. Leaf peepers will love the scenic drives in the area, especially along Route 9 with its rolling hills and colorful forests.

Brattleboro may not be as polished as some of Vermont’s resort towns, but that’s part of its charm. It’s a great place to slow down and enjoy a more local, laid-back vibe.

10. Dorset

Dorset might be small, but it packs in plenty of New England charm. This southern Vermont village is known for its historic marble sidewalks, white clapboard buildings, and a village green surrounded by fiery fall foliage.

Take a walk around the town center to soak up the atmosphere, then stop at the Dorset Union Store for a snack or coffee.

The Dorset Quarry, the oldest marble quarry in the U.S., is also nearby and makes for a quick visit. For leaf peeping, the surrounding country roads are ideal for a leisurely drive.

Dorset has a quiet, laid-back feel that makes it a lovely spot to end a Vermont fall road trip.