Vermont’s picturesque landscapes aren’t just about rolling hills and vibrant foliage—they’re also the backdrop to a rich tradition of artisanal cheesemaking. Scattered across the state are small towns that not only charm visitors with their quaint New England allure but also offer some of the finest cheeses in the country.
From bustling marketplaces to serene village greens, each stop along the Vermont Cheese Trail invites you to savor handcrafted cheeses while soaking up local culture and scenery. Whether you’re a seasoned cheese connoisseur or simply looking for a delightful escape, these 17 small towns provide the perfect blend of taste and tradition. Let’s embark on a flavorful adventure through Vermont’s most delightful cheese destinations.
17. Brattleboro: Cultural Hub with Artisan Cheese Shops
Brattleboro stands as a vibrant gateway to Vermont’s cultural and culinary delights. Nestled along the Connecticut River, this lively town is known for its bustling arts scene and eclectic shops that line historic Main Street. Cheese enthusiasts will find themselves in paradise with an array of artisan cheese shops and locally sourced markets. You can savor handcrafted cheeses at the Brattleboro Farmers’ Market or visit the famed Grafton Village Cheese shop, where traditional methods meet innovative flavors.
Beyond cheese, the town offers live music venues, theaters, and annual festivals that celebrate art and community spirit. Strolling through Brattleboro, you’ll feel the warm embrace of a town that cherishes both its heritage and contemporary flair. With 3-4 bedroom homes averaging $319,845 to $428,114, Brattleboro combines cultural richness with an affordable cost of living.
Where is Brattleboro?
Brattleboro is located in southeastern Vermont, just a stone’s throw from the Massachusetts and New Hampshire borders. Its prime position along Interstate 91 makes it easily accessible for travelers heading north into the heart of the state. The town’s proximity to the Connecticut River not only provides stunning waterfront views but also a rich history as a former mill town. Getting to Brattleboro is a scenic journey in itself, with routes passing through rolling hills and picturesque valleys that epitomize Vermont’s natural beauty.
16. Middlebury: College Town Charm and Cheese Experiences
Middlebury blends small-town charm with a vibrant college atmosphere, making it a delightful stop on Vermont’s cheese trail. Home to Middlebury College, the town buzzes with intellectual energy, historic architecture, and a welcoming community. Cheese lovers can visit local favorites like the Twig Farm or enjoy tastings at Otter Creek Brewing Company, which pairs craft beers with local cheeses. The downtown area boasts boutique shops, art galleries, and cozy cafes perfect for leisurely exploration.
Don’t miss the Middlebury Tasting Trail, where you can indulge in an array of local delicacies including artisanal cheeses and chocolates. With its blend of culture, education, and culinary delights, Middlebury offers a rich experience for visitors. For those considering a home, 3-4 bedroom properties are available with prices ranging from $400,000 to $700,000, reflecting the town’s upscale appeal.
Where is Middlebury?
Middlebury is situated in central Vermont, nestled between the Green Mountains and the shores of Lake Champlain. The town lies along Route 7, one of the state’s main north-south arteries, making it a convenient stop for travelers exploring Vermont’s scenic byways. Its location affords stunning views of rolling hills and access to outdoor activities like hiking and biking. Accessible by car or bus, Middlebury serves as a gateway to the state’s rural heartland, combining ease of access with the tranquility of its natural surroundings.
15. Vergennes: Vermont’s Smallest City with Big Cheese Flavors
Vergennes may hold the title of Vermont’s smallest city, but it offers an outsized experience for cheese aficionados. Its charming downtown, filled with historic buildings, harbors intimate eateries and shops that feature local cheeses and gourmet foods. At the Vergennes Farmers’ Market, you can meet local artisans and sample handcrafted cheeses alongside fresh produce and baked goods.
Just outside the city, nearby farms provide a picturesque backdrop and opportunities to visit creameries where cheesemaking traditions come alive. The city’s intimate setting makes it perfect for leisurely strolls, taking in the quaint architecture and friendly atmosphere. With 3-4 bedroom homes priced between $350,000 and $600,000, Vergennes offers a blend of historic charm and modern comfort.
Where is Vergennes?
Nestled in the Champlain Valley, Vergennes sits just off Route 7, about 25 miles south of Burlington. Its proximity to Lake Champlain offers scenic water views and access to recreational activities like boating and fishing. The city is easily reached by car and serves as a convenient base for exploring the surrounding region’s natural beauty, including the nearby Adirondack Mountains. Vergennes’ location combines the serenity of rural Vermont with the accessibility of larger towns, making it a delightful stop along the cheese trail.
14. Brownington: Historic Village with Dairy Heritage
Brownington is a hidden gem that captures the rich dairy heritage of Vermont within its historic village setting. Stepping into Brownington feels like a journey back in time, especially when you visit the Old Stone House Museum, an icon of the town’s 19th-century roots. The museum offers insights into the area’s agricultural past, including the importance of dairy farming and cheese production. Local farms often open their doors to visitors eager to learn about traditional cheesemaking processes.
The surrounding countryside provides a peaceful backdrop for those looking to escape the hustle and bustle. Brownington embodies the quiet charm and historical depth that make Vermont’s cheese trail so special. With 3-4 bedroom homes ranging from $255,071 to $450,000, this tranquil village offers an affordable retreat steeped in history.
Where is Brownington?
Located in the Northeast Kingdom of Vermont, Brownington rests in one of the most rural and scenic parts of the state. The town is accessible via Route 5, approximately 30 miles south of the Canadian border, offering a serene drive through rolling hills and forests. Its remote location contributes to its untouched beauty and preserves the traditional way of life cherished by its residents. Visitors reaching Brownington are rewarded with panoramic views and a sense of tranquility that’s hard to find elsewhere.
13. Chelsea: Traditional Vermont Village with Local Cheeses
Chelsea is the epitome of a traditional Vermont village, complete with a central green, historic buildings, and a close-knit community. The heart of the town is its picturesque commons, surrounded by charming homes and local businesses that reflect the region’s heritage. Cheese enthusiasts can explore local markets where farm-fresh cheeses are sold alongside other artisanal products.
Nearby farms welcome visitors to experience the pastoral lifestyle and witness cheese production firsthand. The town’s annual events, like the Chelsea Harvest Fair, celebrate agricultural traditions and offer opportunities to taste a variety of local foods. Chelsea invites you to slow down and savor the authentic Vermont way of life. For prospective homeowners, 3-4 bedroom houses average between $250,000 and $461,642, offering a balance of charm and value.
Where is Chelsea?
Chelsea is tucked away in central Vermont, situated along Route 110 in Orange County. The town’s location in a lush valley surrounded by gentle hills contributes to its idyllic rural atmosphere. Though off the beaten path, Chelsea is accessible by scenic country roads that showcase Vermont’s natural beauty at every turn. Its secluded setting is part of its charm, providing a peaceful retreat for visitors seeking an authentic small-town experience on their cheese trail journey.
12. Morrisville: Small-Town Charm Near Cheese Producers
Morrisville offers a delightful blend of small-town warmth and easy access to some of Vermont’s most notable cheesemakers. As the commercial center of Lamoille County, it features a quaint downtown area with locally owned shops, cafes, and restaurants. Cheese lovers can explore nearby producers like Jasper Hill Farm, known for their cave-aged cheeses crafted with care.
The town also serves as a gateway to outdoor adventures, with the Lamoille Valley Rail Trail providing opportunities for biking and hiking amid scenic vistas. Morrisville’s community events, such as farmers’ markets and festivals, highlight the region’s agricultural roots and culinary treasures. It’s a perfect spot to immerse yourself in local culture while indulging in exceptional cheeses. Homes with 3-4 bedrooms typically cost between $350,000 and $600,000, combining accessibility with the appeal of rural Vermont.
Where is Morrisville?
Located in north-central Vermont, Morrisville sits just east of the popular ski town of Stowe, along Route 100. The town is easily accessible, making it a convenient stop for travelers exploring the Green Mountains region. The surrounding area is dotted with rivers, forests, and rolling hills, offering picturesque drives and outdoor recreation. Morrisville’s strategic location provides both the tranquility of a small town and proximity to notable attractions and cheesemakers in the region.
11. Bennington: Historic Sites and Artisan Cheese Shops
Bennington is a town rich in history and cultural significance, offering visitors a blend of heritage and flavor. Famous for the Bennington Battle Monument and its role in the American Revolution, the town invites exploration of its historical landmarks. Artisans in Bennington take pride in crafting exceptional cheeses, which can be found in local shops and farmers’ markets. The Bennington Cheese Shop is a favorite among locals and tourists alike, offering a curated selection of Vermont cheeses and gourmet goods. Beyond cheese, the vibrant arts scene includes galleries and the Bennington Museum, home to works by Grandma Moses. Strolling through Bennington, you’ll experience a town that honors its past while embracing the joys of the present. With 3-4 bedroom homes ranging from $299,900 to $599,000, Bennington provides a perfect mix of historical charm and modern living.
Where is Bennington?
Bennington is situated in the southwestern corner of Vermont, at the junction of Routes 9 and 7, making it a key entry point into the state from New York and Massachusetts. The town is framed by the Green Mountains and the Taconic Range, offering scenic views and easy access to outdoor activities like hiking and skiing. Its location makes it an ideal starting point for exploring the rest of Vermont’s cheese trail. Whether arriving by car or bus, visitors will find Bennington’s blend of accessibility and natural beauty inviting and convenient.
10. Waitsfield: Rustic Beauty and Farm-Fresh Cheeses
Waitsfield exudes rustic charm, with its covered bridges, rolling farmland, and a strong sense of community. Situated in the heart of the Mad River Valley, the town is surrounded by stunning landscapes that change with the seasons. Cheese enthusiasts can savor farm-fresh offerings at local spots like the Von Trapp Farmstead, known for their organic artisanal cheeses. The town’s Saturday Farmers’ Market is a must-visit, where you can mingle with locals and taste a variety of cheeses, produce, and handmade crafts.
Outdoor activities abound, from skiing at nearby resorts to kayaking on the Mad River. Waitsfield provides a perfect blend of relaxation and adventure, all while indulging in some of Vermont’s finest cheeses. With 3-4 bedroom homes averaging $562,478 to $716,951, Waitsfield offers rustic beauty alongside upscale living.
Where is Waitsfield?
Waitsfield is located in central Vermont, accessible via Route 100, which is often dubbed the state’s most scenic roadway. Nestled between the Green Mountains and the Northfield Mountains, the town offers breathtaking views in every direction. Its central location makes it a convenient stop, just a short drive from both Montpelier and Burlington. The journey to Waitsfield is as enjoyable as the destination, with winding roads that showcase the best of Vermont’s natural beauty.
9. Windsor: Vermont’s Birthplace with Local Cheesemakers
Windsor holds the proud title of Vermont’s birthplace, where the state’s constitution was adopted in 1777. This historic town blends its rich past with a burgeoning artisan scene, including exceptional local cheesemakers. At the Windsor Farmers’ Market, you can find a variety of cheeses crafted by nearby farms, each with their own unique flavors.
The town’s attractions include the Old Constitution House and the Cornish-Windsor Covered Bridge, one of the longest wooden covered bridges in the United States. Harpoon Brewery’s Windsor location also offers tours and tastings, pairing their beers with local cheese selections. Windsor’s blend of history, culture, and culinary delights make it a noteworthy stop along the cheese trail. With 3-4 bedroom homes priced from $259,598 to $450,000, Windsor offers historic charm and affordability.
Where is Windsor?
Windsor is located in southeastern Vermont, along the Connecticut River border with New Hampshire, accessible via Interstate 91 and Route 5. The town’s riverside location provides scenic beauty and recreational opportunities like kayaking and fishing. Windsor’s proximity to major routes makes it an easy addition to any travel itinerary through Vermont. Its setting, nestled amidst rolling hills and riverbanks, offers a serene and picturesque landscape for visitors.
8. Waterbury: Gateway to Flavorful Adventures
Waterbury is a town that tantalizes the senses, known not just for cheese but as a hub of Vermont’s most delectable treats. It’s home to the famous Ben & Jerry’s Ice Cream Factory, but cheese lovers will find plenty to savor at the Cabot Annex Store, featuring a vast array of Cabot Creamery’s award-winning cheeses. The town’s vibrant Main Street is lined with specialty shops, cafes, and restaurants that celebrate local ingredients.
Nearby, Cold Hollow Cider Mill offers fresh apple cider and products that pair perfectly with local cheeses. With its lively atmosphere and array of culinary experiences, Waterbury is a flavorful journey waiting to be explored. For those considering a home, 3-4 bedroom properties range from $549,426 to $650,000, reflecting its appeal as a vibrant yet accessible community.
Where is Waterbury?
Situated at the crossroads of Interstate 89 and Route 100, Waterbury is easily accessible from both Burlington and Montpelier. The town is nestled between the Green Mountains and the Winooski River, providing stunning natural scenery and outdoor recreation options. Waterbury’s central location makes it a convenient base for exploring the surrounding attractions, including Stowe Mountain and the Mad River Valley. Whether arriving by car or train, visitors will find Waterbury’s charm and accessibility inviting.
7. Cabot: Birthplace of the Famous Cabot Creamery
Cabot is a small town with a big name in the world of cheese, being the birthplace of the renowned Cabot Creamery Cooperative. This farmer-owned cooperative has been producing high-quality cheeses for over a century, and visitors can tour the creamery to learn about the cheesemaking process.
Beyond the creamery, Cabot offers a quaint rural setting with traditional New England charm. Local farms contribute to the town’s agricultural atmosphere, and you can often find farm stands selling fresh produce and dairy products. Outdoor enthusiasts will appreciate the nearby trails and serene landscapes perfect for hiking and picnicking. With 3-4 bedroom homes averaging $250,000 to $400,000, Cabot combines its cheese heritage with affordability.
Where is Cabot?
Cabot is located in northeastern Vermont, accessible via Route 215 off Route 2, which runs east-west across the state. The town lies amidst rolling hills and lush farmland, offering picturesque drives through the countryside. Its remote location adds to the charm, providing a peaceful retreat from busier tourist areas. Visitors arriving in Cabot will find a warm welcome and a chance to experience Vermont’s rural heritage firsthand.
6. Norwich: Culinary Delights in a Historic Setting
Norwich combines historic charm with culinary excellence, making it a delightful destination for food lovers. The town is home to the King Arthur Baking Company, where visitors can take baking classes or enjoy treats from their on-site café. Cheese enthusiasts will appreciate the selection at local markets and the nearby farms offering artisan cheeses.
The picturesque village green is surrounded by historic homes and buildings, creating a welcoming atmosphere for strolling and shopping. Norwich also hosts the annual Norwich Fair, a community event featuring local foods, crafts, and entertainment. The town’s blend of history, education, and gastronomy provides a rich and satisfying experience. For those seeking a home, 3-4 bedroom properties average between $500,000 and $800,000, reflecting Norwich’s blend of prestige and rural charm.
Where is Norwich?
Norwich is located in eastern Vermont, just across the Connecticut River from Hanover, New Hampshire, home of Dartmouth College. Accessible via Interstate 91 and Route 5, Norwich is conveniently situated for travelers exploring the Upper Valley region. The town’s proximity to the river and surrounding hills offers scenic beauty and opportunities for outdoor recreation. Norwich’s location makes it both a peaceful retreat and a gateway to the broader cultural and educational offerings of the area.
5. Woodstock: Quintessential New England Charm and Artisan Cheese
Woodstock epitomizes the quintessential New England village with its covered bridges, historic inns, and tree-lined streets. The town offers a range of artisan cheeses available at local markets and eateries, making it a delightful stop for food enthusiasts. Nearby, the Billings Farm & Museum provides insights into Vermont’s agricultural history and offers cheese tastings made from their own Jersey cows.
The vibrant downtown area is filled with boutique shops, galleries, and restaurants that celebrate local craftsmanship and farm-to-table dining. Events like the Woodstock Wassail Weekend and summer outdoor concerts add to the town’s lively atmosphere. With 3-4 bedroom homes ranging from $690,869 to $900,000, Woodstock pairs timeless elegance with premium living.
Where is Woodstock?
Woodstock is located in central Vermont, accessible via Route 4, and is about 15 miles west of the New Hampshire border. The town is nestled along the Ottauquechee River, surrounded by rolling hills and lush forests. Its central location makes it an ideal base for exploring other attractions, such as Quechee Gorge and the Long Trail. Woodstock’s combination of accessibility and scenic beauty makes it a popular yet tranquil destination for travelers.
4. Shelburne: Lakeside Beauty and Farmstead Cheeses
Shelburne offers the perfect blend of lakeside tranquility and farmstead charm. The town is home to Shelburne Farms, a 1,400-acre working farm and National Historic Landmark where visitors can tour the grounds, interact with animals, and sample their award-winning farmhouse cheddar cheeses. The stunning views of Lake Champlain add to the allure, providing opportunities for boating and picnicking along the shore.
Shelburne Museum showcases an impressive collection of American art and history, spread across beautifully preserved buildings and gardens. The town’s local markets and restaurants proudly feature Vermont’s cheeses and produce. With 3-4 bedroom homes priced between $500,000 and $850,000, Shelburne combines scenic beauty with high-quality living.
Where is Shelburne?
Shelburne is located just south of Burlington, along the eastern shores of Lake Champlain, accessible via Route 7. Its proximity to Vermont’s largest city makes it easily reachable while offering a peaceful retreat from urban bustle. The town’s lakeside location provides panoramic views of the Adirondack Mountains across the lake in New York. Whether arriving by car or boat, visitors will find Shelburne’s combination of natural beauty and accessibility appealing.
3. Greensboro: Home to Jasper Hill Farm and Scenic Landscapes
Greensboro is a rural gem nestled in Vermont’s Northeast Kingdom, known for its pristine landscapes and artisanal cheeses. The town is home to Jasper Hill Farm, a renowned cheesemaker whose cave-aged cheeses have gained international acclaim. Visitors can arrange tours to glimpse the innovative cheese-aging caves and learn about their sustainable farming practices.
The serene Caspian Lake offers opportunities for swimming, boating, and lakeside relaxation. Greensboro maintains a tight-knit community feel, with local shops and the Highland Center for the Arts providing cultural enrichment. With 3-4 bedroom homes ranging from $350,000 to $600,000, Greensboro offers rural charm with modern comforts.
Where is Greensboro?
Greensboro is situated in the northeastern part of Vermont, accessible via Route 16 and Route 14. The town’s remote location contributes to its peaceful atmosphere and unspoiled natural surroundings. Visitors often enjoy the scenic drives that lead to Greensboro, with panoramic views of rolling hills and farmland. Though off the beaten path, Greensboro’s charm and the draw of Jasper Hill Farm make it a must-visit for cheese enthusiasts.
2. Grafton: Charming Streets and Award-Winning Cheeses
Grafton captivates visitors with its beautifully preserved historic buildings and serene streets lined with maple trees. The town is home to the Grafton Village Cheese Company, where you can watch cheesemakers craft award-winning cheddars using traditional methods. Tasting their cheeses in the on-site shop is a delightful experience, often paired with local wines.
Grafton’s charm extends beyond cheese; the town offers cozy inns, art galleries, and boutique shops that showcase local artisans. Outdoor activities like hiking and biking are popular, with trails winding through picturesque landscapes. With 3-4 bedroom homes priced between $400,565 and $725,000, Grafton combines timeless appeal with a range of housing options.
Where is Grafton?
Grafton is located in southern Vermont, northwest of Bellows Falls, and is accessible via Route 121 and Route 35. The town’s secluded setting amidst rolling hills contributes to its tranquil ambiance. Grafton’s location provides a peaceful escape while still being within reach of larger towns for additional amenities. The scenic routes leading to Grafton are an attraction in themselves, offering glimpses of Vermont’s quintessential countryside.
1. Plymouth Notch: The Historic Village Where Artisan Cheese is Crafted
Plymouth Notch is not only the birthplace of President Calvin Coolidge but also a hub for traditional cheesemaking at the Plymouth Artisan Cheese factory. Founded in 1890 by President Coolidge’s father, the factory continues to produce cheeses using original recipes and antique equipment. Visitors can tour the factory to witness the cheesemaking process and sample a variety of their handcrafted cheeses.
The historic village is impeccably preserved, offering a glimpse into 19th-century rural life with buildings like the Coolidge Homestead and the old general store. The serene surroundings and rich history make Plymouth Notch a unique and enriching stop. For those considering a home, 3-4 bedroom properties range from $300,000 to $500,000, making it a historic yet affordable place to live.
Where is Plymouth Notch?
Plymouth Notch is situated in central Vermont, accessible via Route 100A, nestled between the towns of Bridgewater and Ludlow. The village rests within a tranquil valley surrounded by the Green Mountains, offering stunning natural beauty. Its remote location enhances the historic ambiance, allowing visitors to step back in time undisturbed by modern developments. Plymouth Notch is a rewarding destination for those willing to venture off the main roads to experience a piece of living history.
