Scenic mountain views while hiking the Long Trail in Stowe, Vermont in summer. Image credit Monika Salvan via Shutterstock.

8 Coolest Small Towns in Vermont for a Summer Vacation

Vermont is an undiscovered treasure of New England, renowned for its gorgeous natural landscape, picturesque small villages, and vivacious cultural milieu. From the regal Green Mountains to the crystalline waters of Lake Champlain, Vermont's unspoiled beauty is spellbinding. These towns are ideal for outdoor aficionados and brave explorers, featuring activities like trekking, cycling, canoeing, angling, and snowboarding. If looking for gourmet dining, visitors are bound to fall in love with the farm-to-table fare, microbrewery beer, and homemade cheese that Vermont is famous for. These are 8 coolest small towns in Vermont for a summer holiday waiting for globetrotters to investigate. 

Stowe

Aerial view of the fall colors in the village of Stowe, Vermont
Aerial view of Stowe, Vermont in autumn. Image credit John Couture via Shutterstock.

Nestled in the Green Mountains, Stowe is beautiful and admired by outdoor enthusiasts. Home to the peak of Vermont, Mount Mansfield, it offers tremendous vistas of the bordering country. It is not renowned for winter activities such as skiing and snowboarding, but likewise provides a great number of activities during the summer. One of the most beloved destinations in Stowe is the 5.3-mile Stowe Recreation Path, perfect for taking a stroll, running, cycling, or blading and featuring mesmerizing views of mountains and streams. Additionally, Stowe is well-known for its craft breweries, eateries with food from farms, and rare boutiques, making it attractive for gourmands and buyers alike!

Woodstock

Red barn and church next to a harvested cornfield with the Autumn colors in the background
Landscape of Woodstock, Vermont. Image credit MindStorm via Shutterstock.

Woodstock is a classic New England hamlet with a charming Main Street adorned with historic edifices, specialty stores, and art galleries. It is often referred to as the "loveliest small town in America," and it is easy to see why. The village is enveloped by rolling hills, forests, and meadows, making it a perfect destination for outdoor enthusiasts and trekkers. Woodstock is also the location of the Marsh-Billings-Rockefeller National Historical Park, a 550-acre park that safeguards Vermont's wooded landscape and offers walking, picnicking, and educational programs. One of the must-see attractions in Woodstock is the Billings Farm and Museum, a functioning dairy farm that presents Vermont's agricultural past. Visitors can watch cows being milked, understand how cheese is produced, and investigate the museum's displays and collections.

Manchester

Snowy mountaintop in Manchester, VT. Skier can be seen in frame.
Snowy mountaintop in Manchester, VT. Image credit Claire Levesque via Shutterstock.

Manchester is a fashionable urban area renowned for its lavish boutiques, art galleries, and designer stores. It is a perfect place for consumers who are searching for unique, top-notch products and labels. The city's Main Street has many chic shops, cafes, and eateries, making it an excellent location to enjoy an unhurried afternoon. However, Manchester is more than a shopping spot. It is also a passageway to some of Vermont's most beautiful natural scenes, including the Green Mountains and the Battenkill River. Tourists can go climbing, cycling, angling, or canoeing in the nearby area, or take it easy in one of the city's many spas and getaways. History buffs can visit Hildene, the previous summer home of Abraham Lincoln's son, Robert Todd Lincoln. This estate provides trips to its residence, gardens, and farm, as well as didactic programs and events throughout the year.

Wilmington

 Natural autumn decorations adorn a country inn in Wilmington Vermont.
Crafts Inn in Wilimingston. Image credit James Kirkikis via Shutterstock. 

Wilmington is a beautiful town located in Southern Vermont, near the boundary with Massachusetts. It is well-known for its appealing Main Street full of bright edifices, master craftsmen stores, and inviting cafes. Wilmington is also the home of the Mount Snow ski resort, which offers some of the most prime skiing and snowboarding in the state, as well as diverse pastimes all year-round comprising hiking, mountain biking, and golf. One of the singular points of interest in Wilmington is the Molly Stark State Park, a 168-acre area that has gorgeous trails, picnic areas, and a campsite. The park is commemorated after Molly Stark, the partner of Revolutionary War General John Stark, who directed a fight against British armies in the region in 1777. Guests can examine the park's story and natural loveliness, and relish activities like swimming, boating, and fishing in a near lake in the summer.

Middlebury

Beautiful waterfall in east Middlebury, Vermont.
Waterfall in east Middlebury. Image credit Josh Hummel via Shutterstock.

Middlebury is an animated university town that's replete with history and culture. It is home to Middlebury College, one of the preeminent liberal arts colleges in the nation, as well as many art galleries, museums, and theaters. The town's Main Street has many antique buildings, remarkable stores, and intimate coffee shops, making it a perfect choice for a relaxed walk or a coffee. One of the must-see attractions in Middlebury is the Henry Sheldon Museum of Vermont History, an absorbing museum that illustrates Vermont's history and culture. The museum holds collections of art, artifacts, and archives, as well as exhibits on matters like the Civil War, the Abenaki Native Americans, and Vermont's farming pedigree. Middlebury is also an amazing foundation for exploring the neighboring natural attractions, such as the Green Mountains, Lake Champlain, and the neighboring state parks.

Waterbury

Ben & Jerry's Ice Cream Factory in Waterbury.
Ben & Jerry's ice cream factory in Waterbury. Image credit Wangkun Jia via Shutterstock.

Waterbury is a small town situated in the core of Vermont, distinguished for its breweries, farm-to-table dining, and handcrafted items. It is the ideal destination for gourmets in search of unique, top-notch products and flavors. The city is abode to several of Vermont's most renowned breweries, for instance, the Alchemist and the Prohibition Pig, which offer sampling, outings, and different events throughout the year. One of the most attractive sites in Waterbury is the Ben & Jerry's Factory, a renowned ice cream manufacturer that provides guided tours, tastings, and activities for all ages. Vacationers can dive into the past of the enterprise, observe how to make ice cream and savor some of the most preferred flavors. Waterbury is also an excellent base for exploring the neighboring attractions, such as the Green Mountains, the Stowe Ski Resort, and the nearby state parks. This is an absolute must-go spot for the summertime holiday!

Weston

Aerial view of Weston Vermont during the colorful fall season.
Aerial view of small town Weston in autumn. Image credit John Couture via Shutterstock.

Tucked away in the undulating hills of southern Vermont, Weston is a diminutive village embodying the quintessential New England community. With a population not exceeding 600, this tranquil hamlet is the ideal destination for vacationers seeking to evade the hustle and bustle of city life. For nature aficionados, Weston is home to the Weston Priory, a Benedictine monastery spread across 500 acres of terrain. Tourists can go on hikes, appreciate the picturesque views, and attend Mass or supplication services. One of Weston's chief attractions is the Weston Playhouse, a celebrated theater having staged Broadway-quality shows for more than 80 years. The playhouse locates in a vintage 19th-century building and presents a broad array of performances throughout the summer months.

Waitsfield

Barn and mountains in the Waitsfield landscape.
Barn and mountains in Waitsfield. Image credit Cvernet Photography via Shutterstock.

Situated in the middle of the Mad River Valley, Waitsfield is a beauteous town that provides an ideal blend of outdoor recreation and small-town enchantment. The town is near the amazing Green Mountains, and the Mad River furnishes rich prospects for aquatic sports such as kayaking, canoeing, and angling. Waitsfield also harbors many state parks, including the Mad River Glen Natural Area and Camel's Hump State Park. These preserves give a selection of activities, including hiking, mountain biking, and wildlife watching. For those who opt for a mild tempo, Waitsfield's antique-covered bridges and quaint retail and eateries offer glimpses into Vermont's affluent past and culture. The town is also recognized for its lively arts scene, with art galleries and ateliers exhibiting the works of local painters.

Conclusion

If searching for a summer holiday spot that presents an ideal blend of outdoor escapades, provincial allure, and affluent cultural encounters, Vermont's eight most amazing little towns are an optimal selection. From the unbelievable natural loveliness of Stowe and Waterbury, to the affluent cultural contributions of Middlebury and Weston, these towns proffer something for everyone. Whether to traverse the beautiful paths, catch a performance of Broadway standard, or recline and savor the landscape, Vermont's small towns are an ideal summer vacation destination. So stuff your suitcases, grab your hiking boots, and be set to explore some of the coolest small towns in America!

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