Top 20 Festive Vermont Towns to Visit this Fall 

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With picturesque villages and stunning landscapes, Vermont comes alive in the fall. As the leaves change color and the air turns crisp, the Green Mountain State transforms into a vibrant wonderland, making it the perfect destination for a festive autumn getaway.

In this blog post, I’ll cover the top 20 festive places to visit in Vermont in the fall. From charming downtowns and quaint villages nestled among rolling hills to vibrant communities with bustling fall festivals, all of these towns make a great stop on a New England autumn road trip. While a few are small (taking less than 5 mins to drive down Main St.) and more secluded, most of these small towns have a variety of activities, shops and eateries to easily fill your day.


Nestled in northeast Vermont, Westmore is the epitome of small-town New England charm. This quaint village, with a population of just over 300 residents, is a place where time seems to stand still. 

The best part of visiting Westmore is that you’ll have easy access to Lake Willoughby, often referred to as the “Lucerne of America” due to its stunning resemblance to the Swiss lake. Visitors are drawn to the crystal-clear waters and towering cliffs that frame this body of water, creating a natural oasis for swimming, hiking, and kayaking. Even if it’s cold during your visit, the scenery alone makes it worth visiting.

Westmore is also home to Willoughby State Forest, providing countless opportunities for outdoor adventures, from hiking the 5.9-mile Mount Pisgah trail to leaf-peeping amidst vibrant peak foliage.


As you walk through this adorable town, with its colonial architecture and welcoming atmosphere, you’ll feel like you’re stepping back in time. 

Located in northern Vermont, Montgomery is renowned for its stunning covered bridges, including the Comstock Bridge and the Hutchins Bridge, both built in 1883 – these are quintessential Vermont landmarks! 

The town also boasts proximity to the beautiful Jay State Forest, offering year-round recreational opportunities, from skiing in the winter to hiking and mountain biking in the warmer months. 


Quechee is one of five villages in the larger Hartford, Vermont area. One of the most notable attractions in this village is the 165-foot-deep Quechee Gorge, often dubbed the “Little Grand Canyon of Vermont.” 

While you’re here, you can stroll along the impressive bridge that spans the gorge or hike down to the gorge’s bottom on the Quechee Gorge Trail to witness the dramatic waterfalls and rugged terrain. This gorge is part of the larger Quechee State Park, an excellent place for camping, fishing, picnicking, and hiking. 


Located in northern Vermont, Stowe is perhaps best known for its world-renowned Stowe Mountain Resort, a winter wonderland that transforms into a lush playground for outdoor enthusiasts in the summer and fall.

If you’re seeking stunning vistas for stunning foliage views, a trip to the top of Mount Mansfield is a must. Vermont’s highest peak offers sweeping panoramic views of the surrounding landscape and is accessible via the historic Auto Toll Road, a scenic drive that winds its way up the mountain. 

During fall, a drive down the curvy Smugglers Notch road lined with 1000-foot cliffs is a must-do. You may also enjoy a stay at the Trapp Family Lodge, owned by the famous von Trapp family from “The Sound of Music.” This Austrian-inspired resort will make you feel like you’ve been transported straight to Bavaria. 

If you’re yearning for more outdoor adventure, head to Underhill State Park, located within the 39,837-acre Mt. Mansfield State Forest and on the west slope of Mt. Mansfield. Here, you can enjoy outdoor activities galore, from mountain biking and hiking to stream fishing and wildlife viewing. 



The small town of Waitsfield is an ideal destination for outdoor enthusiasts, with activities such as hiking, biking, and skiing in the nearby Mad River Glen. Waitsfield’s quaint village center boasts a vibrant arts and cultural scene, with historic buildings, boutique shops, and an array of local eateries celebrating farm-to-table cuisine.

Don’t forget to visit the Waitsfield Covered Bridge, also known as the Great Eddy Covered Bridge. Constructed in 1833, it’s one of the oldest covered bridges in Vermont. 


Located in the Mad River Valley, close to Waitsfield, Warren is set between two ranges of the Green Mountains, making this one of the best mountain towns in Vermont. Sugarbush Ski Resort is one of the best places to stay, and it is beautiful any time of year. If it’s warm during your visit, check out Warren Falls. You can hike the short path that leads to stepped waterfalls with fantastic natural swimming holes and cliff jumping.


Surrounded by the rolling hills and dense forests of Lamoille County, Jeffersonville provides a peaceful escape for outdoor enthusiasts. This village, part of the larger town of Cambridge, Vermont, is home to the popular Smugglers’ Notch Resort, a paradise for winter sports enthusiasts with superb skiing and snowboarding terrain. 

Jeffersonville’s quaint village center boasts historic architecture, local shops, and cozy eateries showcasing Vermont’s farm-to-table tradition. Recharge here after a full day of outdoor activities!

For a dose of history, visit the Grist Mill Covered Bridge, also known as the Scott Covered Bridge. This was constructed in the 19th century and is one of the only surviving Burr arch-truss bridges in the state – one of three left in Cambridge, Vermont.

Before you leave, don’t forget to visit Vermont Maple Outlet for some of the best maple products in the state – the maple ice cream is a fan favorite!


Besides the Green Mountains’ stunning natural beauty, Waterbury is known as a hub for ice cream enthusiasts. Visit the Ben and Jerry’s Factory to tour the production facility, learn about the history of this iconic brand, and get a free ice cream sample. Chances are, you’ll want more than just a sample – order exclusive flavors at the onsite ice cream shop!

For those with a taste for something a bit more tart, the nearby Cold Hollow Cider Mill is a must-visit, where you can savor freshly pressed apple cider and an array of apple-based products, including fresh apple cider donuts. 


Nestled on the shores of Lake Champlain, Burlington serves as Vermont’s cultural and economic hub. Known for its picturesque setting with views of the Adirondack Mountains and the lake, Burlington perfectly blends natural beauty and urban culture. 

This city’s downtown area is a bustling cultural and culinary center with various locally owned shops, eateries, and a thriving arts scene. Strolling along Church Street Marketplace, a lively pedestrian mall, you can immerse yourself in the city’s eclectic energy and find an array of dining options ranging from farm-to-table restaurants to cozy cafés – Ri Ra Irish Pub and Leunig’s Bistro are two local favorites. 

Burlington is also home to the University of Vermont, adding a youthful flair to the city’s atmosphere. Outdoor enthusiasts will appreciate the city’s proximity to recreational opportunities, including the Burlington Waterfront, where you can enjoy lakeside parks, the Burlington Greenway Bike Path, and breathtaking sunsets over Lake Champlain. 



Known for its breathtaking waterfront location on Lake Champlain, about 7 miles south of Burlington, Shelburne abounds in natural beauty and cultural heritage. One of the town’s highlights is the Shelburne Museum, showcasing a vast collection of Americana, folk art, and historical artifacts in a beautiful campus with meticulously preserved historic buildings. Out of 39 different buildings, 25 of these are historic!

This town is also home to the stunning Shelburne Farms, a historic working farm and educational center with magnificent landscapes, walking trails, a fantastic bakery, and farm-to-table produce. Pet the farm animals and then sit down for a bite to eat at the onsite restaurant. 

Shelburne’s marina and the Shelburne Shipyard are popular spots for boating and enjoying the picturesque views of Lake Champlain and the Adirondack Mountains. In the fall, visiting the local apple orchards is a must – Shelburne Orchards, a family-owned joint with apple cider donuts, is one of my favorite places!


This tiny community, home to about 1,200 residents, is known for its stunning landscapes and location along the scenic Route 100, which winds through some of Vermont’s best scenic views. Settled by Quakers in the late 18th century, Lincoln is surrounded by lush forests, making it home to the best fall colors during this season. It’s also a perfect destination for outdoor enthusiasts, with numerous hiking trails, fishing spots, and opportunities for birdwatching.


With a charming town square known as the Green, surrounded by historic buildings, Woodstock is one of the best places to visit in Vermont in the fall.

This town is home to the Billings Farm and Museum, a living history museum and dairy farm that offers a glimpse into Vermont’s rural heritage, complete with a working farm, educational exhibits, and an 1890s farmhouse. 

Surrounded by the rolling hills and verdant pastures of the Green Mountains, Woodstock offers numerous opportunities for outdoor exploration, from hiking and mountain biking to exploring the serene Ottauquechee River. You can also explore the Marsh-Billings-Rockefeller National Historical Park; this forested landscape, showcasing vibrant fall colors, also offers tours of a Victorian mansion.


As the capital city of Vermont, Montpelier exudes a unique blend of history, culture, and natural beauty. Despite its modest size, Montpelier is the nation’s smallest state capital, reflecting Vermont’s community values. 

This city’s downtown area boasts picturesque streets lined with historic buildings, boutique shops, and locally owned restaurants, making it the best place for a leisurely stroll. The Vermont State House, an architectural masterpiece with a gleaming gold dome, is a prominent landmark and a symbol of Vermont’s democratic ideals. You can explore this historic building, which houses the state’s legislative chambers and offers guided tours.

Surrounded by the lush landscapes of the Green Mountains, Montpelier is also a gateway to outdoor adventures, with opportunities for hiking in the nearby Hubbard Park. The highlight of this park is the Observation Tower, located at the highest point – there’s no better place to admire views of the surrounding area, splashed with the colors of red, yellow, and orange throughout the autumn.


Nestled in the heart of the Champlain Valley, Middlebury is one of the best places to visit in Vermont in the fall. The town is home to Middlebury College and exudes a youthful vibrancy and intellectual atmosphere. The adorable village center features quaint streets, stone architecture, elegant 19th-century buildings, and boutique shops. 

While visiting in the fall, head to one of the nearby apple orchards. Happy Valley Orchard is one of my favorite places to go apple picking. While you’re here, you can sip fresh apple cider and sample apple cider donuts.

Surrounded by the Green Mountains and the Adirondacks, Middlebury offers outdoor enthusiasts various recreational opportunities, from hiking in the nearby Green Mountain National Forest to exploring Branbury State Park’s pristine lake and wooded trails. Otter Creek runs through the heart of Middlebury, providing a serene backdrop for leisurely walks and picnics. The Middlebury College Museum of Art and the Town Hall Theater contribute to the town’s cultural vibrancy, providing a wide range of exhibitions, collections, and live shows.



The tiny community of Peacham is known for its scenic beauty, characterized by rolling hills, quaint farms, and the Peacham Historic District with its well-preserved 19th-century architecture. This town’s breathtaking views of the surrounding countryside, especially during the fall season, make it a popular destination for travelers who want to experience the beauty of Vermont fall foliage in solitude.

With numerous hiking trails and the Peacham Bog Natural Area, outdoor enthusiasts can explore the unspoiled wilderness of Vermont. You can also check out the Owls Head Hiking area, a 4-mile out-and-back trail that leads to an incredible scenic vista showcasing Lake Groton, Kettle Pond, and the Green Mountains. 


Located in Southern Vermont, Manchester’s adorable village center features well-preserved colonial and Victorian architecture. Manchester also happens to be a shopper’s paradise, with designer outlets, boutiques, and antique stores lining its streets, making it a popular destination for retail therapy.

Surrounded by the Taconic and Green Mountains lush landscapes, Manchester is an outdoor enthusiast’s dream, with several hiking and skiing opportunities nearby. Equinox Mountain, one of Vermont’s highest peaks, offers breathtaking views from the summit and an extensive trail network – this is one of the best places to visit in Vermont in the fall for stunning foliage views.


Located in southern Vermont’s Windham County, Grafton exudes a sense of timelessness that aligns with Vermont’s rural traditions. Grafton is particularly famous for the Grafton Village Cheese Company, which produces award-winning cheddar cheese and offers tours and tastings. 

Surrounded by the lush forests of the Green Mountains, Grafton boasts a tranquil escape for nature enthusiasts, with ample opportunities for hiking, snowshoeing, and cross-country skiing. Be sure to check out the Bartonsville Covered Bridge, just a short drive from town – this historic bridge is postcard-worthy!

If you want to stay overnight in this beautiful area, the Grafton Inn, dating back to 1805, provides a cozy and welcoming place to stay in the center of town.


Founded in 1761, Dorset boasts a well-preserved village center with colonial and Federal-style architecture. Start by visiting the Dorset Union Store, which has operated for over 200 years. Here, you can browse for Vermont products, bakery items, and even dinner on the go. You can also stop by the Dorset Farmers Market, a year-round produce market with tons of local vendors. This is one of the best places to visit in Vermont in the fall!

Dorset is surrounded by the scenic beauty of the Green Mountains, providing ample opportunities for outdoor activities. Hiking, biking, and winter sports are popular activities, with nearby destinations like the Dorset Quarry, a historic marble quarry that is now a popular swimming hole in the summer. 

This town is also famous for its cultural attractions, such as the Dorset Theatre Festival, which showcases a variety of plays and performances throughout the summer. 


Located in southern Vermont, Bennington’s downtown area boasts a classic New England vibe with colonial and Federal-style architecture, complemented by boutique shops, cozy restaurants, and the iconic Bennington Battle Monument, which commemorates the pivotal Battle of Bennington during the American Revolution.

Surrounded by the rolling hills and valleys of the Green Mountains, Bennington offers a wide array of outdoor activities, from hiking along the Appalachian Trail to exploring nearby state parks like the Woodford State Park and Lake Paran Recreation Area. 

A visit to the stunning Park-McCullough Historic Governor’s Mansion is a must see when visiting north Bennington. This Victorian estate on 200 acres with a playhouse and lush garden offers guided tours and seasonal events through early October.

This town is also home to Bennington College, known for its progressive approach to education and contributions to the arts. The Bennington Museum showcases the region’s cultural history and artistic heritage, featuring works by Grandma Moses (a 20th-century folk artist) and other notable artists. 

Bennington’s annual Garlic Town USA is a popular event in early September, drawing visitors to celebrate local cuisine and artisanal products. 


Nestled on the backroads of Vermont, Wilmington is one of the best places for leaf-peeping in Vermont. The town’s village center showcases historic buildings, boutique shops, and an impressive variety of cozy restaurants. Visitors often enjoy strolling along the scenic Main Street, savoring fresh and local cuisine, and browsing local artisanal crafts.

Wilmington is surrounded by abundant outdoor opportunities. The nearby Mount Snow Resort provides world-class winter sports activities and mountain views, while the summer offers hiking, mountain biking, and water sports on Lake Whitingham, known as “Harriman Reservoir.” The town is also home to the Southern Vermont Natural History Museum, showcasing the region’s wildlife and ecology.


Situated in Southern Vermont, Battleboro is known for its artistic flair. This town’s downtown area features a bustling arts scene, with galleries, music venues, and theater, including the Metropolitan Opera and world-class aerial arts. The Brattleboro Museum and Art Center is a fantastic attraction for art enthusiasts, housing regional and international artists. 

Surrounded by the scenic beauty of the Connecticut River and the Green Mountains, Brattleboro abounds in outdoor adventures, especially in the fall. Hiking, cycling, and kayaking are popular activities, and nearby natural attractions like the Retreat Trails and Fort Dummer State Park provide ample opportunities for foliage viewing. 

Before you leave, check out the charming Creamery Covered Bridge and grab a bite at the Vermont Country Deli just a short walk down the road. Over in West Dummerston, about a 15-minute drive from Brattleboro you can visit the West Dummerston Covered Bridge, dating back to 1872. At 280 feet long, this bridge is the longest covered bridge in the state of Vermont! There is an onsite parking lot and stairs leading down to the river bank.


As you can tell, there are many wonderful small towns and villages worth a visit in Vermont. With always something new to uncover, Vermont is a wonderful state to explore all year around but especially on a fall foliage road trip.

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