Route 100, often referred to as "The Skier's Highway," stretches over 200 miles through the heart of Vermont, weaving its way from the Massachusetts border up to the Canadian border. This scenic byway is the epitome of New England charm, guiding you through quaint villages, serene lakes, towering mountains, and rolling farmlands. Whether you're visiting during the vibrant fall foliage, the lush summer, or the snow-covered winter, Route 100 offers a quintessential Vermont experience filled with natural beauty, outdoor adventures, and small-town hospitality.

Stops along the Route 100

Wilmington (1-2 days)

Wilmington, situated at the southern entrance of Route 100, is a charming village that perfectly captures the essence of Vermont. Known for its well-preserved historic architecture, Wilmington is a place where time seems to stand still. The town offers a wonderful mix of outdoor activities, boutique shopping, and cozy dining options. Wilmington's scenic surroundings make it a great starting point for your journey up Route 100.

Sights

• Harriman Reservoir: Also known as Lake Whitingham, this expansive reservoir is the largest body of water entirely within Vermont. The reservoir is a paradise for outdoor enthusiasts, offering activities like kayaking, paddleboarding, and fishing in the summer, and ice fishing in the winter. The calm waters and surrounding forest create a peaceful setting, perfect for a relaxing picnic or an invigorating hike along the shoreline.
• Molly Stark State Park: Named after the wife of Revolutionary War General John Stark, this state park is a hidden gem for hikers and nature lovers. The park offers several trails that lead to stunning vistas of the Green Mountains, especially vibrant during the fall foliage. It’s also a great spot for camping, with well-maintained campsites nestled among the trees.
• Downtown Wilmington: Strolling through Wilmington’s downtown feels like stepping back in time. The village is home to a variety of antique shops, art galleries, and local cafes, all housed in beautifully preserved buildings. The atmosphere is laid-back, making it easy to spend a leisurely afternoon browsing through unique finds or enjoying a coffee in one of the quaint cafes.
• The Village Roost: This beloved local eatery is known for its fresh, locally sourced ingredients and welcoming atmosphere. Whether you’re stopping in for a hearty breakfast or a light lunch, you’ll find the food here both delicious and comforting. The maple latte and Vermont cheddar grilled cheese are particularly popular choices.

Dover (1 day)

Just a short drive north of Wilmington, Dover is a small town that comes alive during the winter months thanks to Mount Snow, one of Vermont’s premier ski resorts. But Dover isn’t just for winter sports enthusiasts; it’s a year-round destination with plenty of outdoor activities, from hiking and mountain biking in the summer to foliage drives in the fall.

Sights

• Mount Snow: As one of Vermont’s largest ski resorts, Mount Snow is a magnet for skiers and snowboarders. The resort boasts a wide variety of trails catering to all skill levels, from beginner slopes to challenging black diamonds. In the summer, the mountain transforms into a playground for hikers and mountain bikers, with scenic trails and lift-served access to the summit. The panoramic views from the top are breathtaking, particularly during the fall when the mountains are ablaze with color.
• Hogback Mountain: Famous for its "100-Mile View," Hogback Mountain offers one of the most stunning vistas in southern Vermont. On a clear day, you can see three states—Vermont, Massachusetts, and New Hampshire—from the overlook. This area is also home to several hiking trails that range from easy walks to more challenging climbs, making it a perfect stop for nature lovers.
• Southern Vermont Natural History Museum: Located at the Hogback Mountain Scenic Overlook, this small but fascinating museum is dedicated to the wildlife and natural history of the region. The museum’s exhibits include a wide variety of local fauna, from birds of prey to small mammals, and offer an educational experience for visitors of all ages. The museum’s location also provides access to nearby hiking trails and picnic areas.

Weston (1 day)

Weston is a quintessential New England village that feels like it’s been frozen in time. With its historic buildings, charming shops, and cultural institutions, Weston is a place where tradition and beauty come together in perfect harmony. This small village is an ideal stop for those looking to experience the slower pace of rural Vermont life, complete with old-fashioned general stores and classic white-steepled churches.

Sights

• The Vermont Country Store: A visit to Weston wouldn’t be complete without stopping at The Vermont Country Store. Founded in 1946, this legendary general store is a treasure trove of nostalgic products, from classic toys and candies to Vermont-made goods like maple syrup and cheese. The store’s creaky wooden floors and friendly staff make it feel like a step back in time, and it’s easy to spend hours exploring the many aisles filled with unique and hard-to-find items.
• Weston Playhouse: Established in 1937, the Weston Playhouse is Vermont’s oldest professional theater and a cultural cornerstone of the community. The playhouse offers a wide range of performances, from classic plays and musicals to contemporary productions. If you’re visiting during the summer, be sure to check the schedule for performances; the theater’s intimate setting and high-quality productions make for a memorable evening.
• Weston Priory: Tucked away in the hills surrounding Weston, the Weston Priory is a Benedictine monastic community that offers a place of peace and reflection. Visitors are welcome to attend services, walk the scenic grounds, or simply enjoy the tranquility of the priory’s setting. The priory’s gift shop offers a selection of handmade items, including pottery and religious art, crafted by the monks.
• West River: Flowing through the village of Weston, the West River is a beautiful spot for a leisurely walk or picnic. The river is flanked by lush greenery and offers several peaceful spots to sit and enjoy the natural surroundings. In the fall, the area is particularly stunning as the leaves change color, reflecting brilliantly in the clear waters of the river.

Ludlow (1-2 days)

Nestled in the shadow of Okemo Mountain, Ludlow is a vibrant town that attracts visitors year-round. While the town is best known for its ski resort, Ludlow offers a variety of activities and attractions no matter the season. From exploring the outdoors to discovering local history, Ludlow has something for everyone.

Sights

• Okemo Mountain Resort: Okemo is one of Vermont’s most popular ski resorts, drawing visitors with its extensive network of trails, family-friendly atmosphere, and top-notch amenities. In the winter, skiers and snowboarders of all levels flock to the mountain to enjoy the powder-covered slopes. During the warmer months, Okemo offers a range of activities including a mountain coaster, zip lines, and golf. The resort’s summit provides panoramic views that are particularly striking in the fall, making it a great destination for leaf peepers.
• Buttermilk Falls: Just a short drive from downtown Ludlow, Buttermilk Falls is a series of picturesque waterfalls that cascade into clear, cool pools below. The falls are a popular spot for swimming during the summer, and the surrounding woods provide a peaceful setting for a hike or picnic. In the winter, the frozen falls create a stunning natural ice sculpture that’s worth braving the cold to see.
• Ludlow Village Historic District: Ludlow’s historic district is a charming area that offers a glimpse into the town’s past. The district is home to several well-preserved buildings, including the Black River Academy Museum, which was once attended by President Calvin Coolidge. The museum offers exhibits on local history, including the town’s role in the development of the region. The village is also home to a variety of shops, cafes, and restaurants, making it a great place to spend a leisurely afternoon.
• The Ludlow Cooking Company: Known for its delicious sandwiches, salads, and baked goods, The Ludlow Cooking Company is a favorite among locals and visitors alike. The menu features a variety of fresh, locally sourced ingredients, and the cozy atmosphere makes it a perfect spot for a relaxed meal. Don’t miss the chance to try one of their homemade desserts, which are the perfect way to end your visit to Ludlow.

Woodstock (2 days)

Woodstock is often hailed as one of the most beautiful towns in America, and it’s easy to see why. With its perfectly preserved historic buildings, covered bridges, and vibrant cultural scene, Woodstock is a picture-perfect representation of small-town New England charm. The town offers a blend of natural beauty and sophisticated amenities, making it an ideal stop for those seeking both relaxation and cultural enrichment.

Sights

• Billings Farm & Museum: Established in 1871, Billings Farm is a working dairy farm and museum that offers a fascinating look into Vermont’s agricultural history. Visitors can tour the farm’s historic barns, interact with farm animals, and learn about the history of dairy farming in the region. The museum also hosts seasonal events, including harvest festivals and traditional craft demonstrations, making it a great destination for families.
• Marsh-Billings-Rockefeller National Historical Park: As the only national park in Vermont, Marsh-Billings-Rockefeller National Historical Park is a unique destination that combines history, conservation, and natural beauty. The park’s mansion and gardens were once the home of conservationist Frederick Billings, and today, visitors can tour the beautifully preserved estate and explore the surrounding trails that wind through old-growth forests and rolling pastures. The park is particularly stunning in the fall when the foliage creates a kaleidoscope of colors.
• Middle Covered Bridge: One of Woodstock’s most iconic landmarks, the Middle Covered Bridge spans the Ottauquechee River and offers a picturesque view of the surrounding countryside. The bridge is a popular spot for photographers, especially during the fall when the leaves turn vibrant shades of red, orange, and yellow. A walk across the bridge is a must for any visitor to Woodstock, offering a quintessential Vermont experience.
• Woodstock Village: The heart of Woodstock, the village is home to a variety of boutique shops, art galleries, and cafes. The historic buildings that line the streets have been carefully preserved, giving the village a timeless quality that’s both charming and inviting. Whether you’re browsing for unique gifts, enjoying a meal at one of the local restaurants, or simply taking in the sights, Woodstock Village is a delightful place to explore.

Waterbury (1 day)

Waterbury is a small town with a big reputation, thanks to its status as the home of Ben & Jerry’s ice cream. But there’s more to Waterbury than just sweet treats; the town is surrounded by stunning natural beauty and offers a variety of outdoor activities, making it a great stop for adventurers and foodies alike.

Sights

• Ben & Jerry’s Factory: A visit to the Ben & Jerry’s Factory is a must for any ice cream lover. The factory offers guided tours that take you through the ice cream-making process, from cow to cone. At the end of the tour, you’ll get to sample some of the company’s famous flavors, including limited-edition varieties that aren’t available anywhere else. Don’t miss the Flavor Graveyard, where you can pay your respects to discontinued flavors that are no longer in production.
• Cold Hollow Cider Mill: Located just a short drive from downtown Waterbury, Cold Hollow Cider Mill is a traditional cider mill that offers visitors a taste of Vermont’s apple heritage. Watch as fresh cider is pressed from locally grown apples, and sample the mill’s famous cider donuts, which are made fresh daily. The mill’s gift shop is filled with Vermont-made products, including maple syrup, cheeses, and specialty foods, making it a great place to pick up souvenirs.
• Waterbury Reservoir: Nestled in the mountains, Waterbury Reservoir is a popular spot for outdoor recreation. The reservoir is surrounded by hiking trails that offer stunning views of the water and surrounding forests, making it a great destination for a peaceful hike or a day of kayaking or fishing. The area is particularly beautiful in the fall when the foliage reflects in the calm waters, creating a mirror-like effect.
• Prohibition Pig: Known for its craft beer and delicious BBQ, Prohibition Pig is a must-visit for foodies traveling through Waterbury. The restaurant offers a relaxed atmosphere and a menu filled with smoked meats, inventive sides, and a wide selection of local beers. It’s the perfect place to unwind after a day of exploring, and the friendly staff will make you feel right at home.

Stowe (2 days)

Stowe is often referred to as the “Ski Capital of the East,” but this charming town offers much more than just winter sports. Nestled at the base of Mount Mansfield, Vermont’s highest peak, Stowe is a year-round destination with stunning scenery, outdoor adventures, and a vibrant arts scene. Whether you’re hitting the slopes, hiking the trails, or exploring the village, Stowe is a place where you can experience the best of Vermont’s natural beauty and cultural offerings.

Sights

• Stowe Mountain Resort: Stowe Mountain Resort is a premier destination for outdoor enthusiasts, offering world-class skiing and snowboarding in the winter, and hiking, biking, and golf in the summer. The resort’s gondola ride to the summit of Mount Mansfield offers breathtaking views of the surrounding mountains and valleys, making it a must-do activity any time of year. The resort also offers a range of dining and shopping options, as well as luxury accommodations for those looking to extend their stay.
• Mount Mansfield: Standing at 4,393 feet, Mount Mansfield is the highest peak in Vermont and a favorite destination for hikers and nature lovers. The Long Trail, which runs the length of Vermont from Massachusetts to Canada, crosses the summit, offering challenging hikes and unparalleled views. The mountain is home to a variety of plant and animal species, including rare alpine flora, making it a unique destination for those interested in ecology and conservation.
• Stowe Recreation Path: This 5.5-mile paved path winds through the town of Stowe, offering a scenic route for walking, biking, or rollerblading. The path follows the West Branch of the Little River, passing through meadows, forests, and farmland, with stunning views of the surrounding mountains. The path is accessible year-round and is a popular spot for both locals and visitors looking to enjoy a leisurely outdoor experience.
• Trapp Family Lodge: Founded by the famous von Trapp family from “The Sound of Music,” the Trapp Family Lodge is a unique destination that offers Austrian-inspired accommodations, cross-country skiing, and scenic hikes. The lodge is set on 2,500 acres of land, with miles of trails that wind through forests and meadows, offering beautiful views of the Vermont countryside. The lodge’s on-site brewery, von Trapp Brewing, offers a selection of craft beers that pair perfectly with the lodge’s farm-to-table cuisine.

Morrisville (1 day)

Just north of Stowe, Morrisville is a quieter, more laid-back town that offers a glimpse into everyday life in rural Vermont. With its charming downtown, scenic trails, and local breweries, Morrisville is a great place to slow down and enjoy the simple pleasures of small-town life.

Sights

• Lamoille Valley Rail Trail: This 93-mile trail follows the route of the old St. Johnsbury & Lamoille County Railroad, offering a scenic route for biking, walking, and snowshoeing in the winter. The trail passes through picturesque farmland, forests, and small towns, with stunning views of the Lamoille River and the surrounding mountains. The trail is a great way to explore the natural beauty of the region at a leisurely pace.
• Green River Reservoir State Park: Located just outside of Morrisville, Green River Reservoir State Park is a peaceful spot for kayaking, canoeing, and fishing. The park is known for its quiet waters and scenic campsites, which are accessible only by boat, offering a true wilderness experience. The reservoir is surrounded by miles of hiking trails, making it a great destination for those looking to escape into nature.
• Rock Art Brewery: Founded in 1997, Rock Art Brewery is a local craft brewery known for its creative and flavorful beers. The brewery’s tasting room offers a relaxed atmosphere where you can sample a variety of brews, including the popular “Vermonster” barleywine. The brewery also offers tours that provide a behind-the-scenes look at the brewing process, making it a must-visit for beer enthusiasts.
• Morrisville Village: The village of Morrisville is a charming area with a mix of historic buildings, local shops, and eateries. The downtown area offers a variety of unique shops where you can find locally made crafts, gifts, and Vermont specialties. The village’s friendly atmosphere and small-town charm make it a great place to spend a leisurely afternoon.

Jay (1 day)

Located near the Canadian border, Jay is the northernmost stop on Route 100 and is home to Jay Peak Resort, a popular destination for skiing and year-round activities. Jay offers a mix of outdoor adventure and small-town charm, making it a perfect final stop on your Route 100 journey.

Sights

• Jay Peak Resort: Jay Peak is one of Vermont’s premier ski resorts, offering some of the best skiing and snowboarding in the state. The resort’s location near the Canadian border means it often gets more snow than other areas, making it a favorite among winter sports enthusiasts. In the summer, the resort offers hiking, golf, and the popular Jay Peak Pump House Indoor Waterpark, making it a great destination for families.
• Jay Peak Aerial Tramway: The aerial tramway at Jay Peak offers a unique way to experience the stunning scenery of northern Vermont. The tramway takes you to the summit of Jay Peak, where you can enjoy 360-degree views of Vermont, New Hampshire, and Canada. On a clear day, you can see for miles, making it one of the most scenic spots in the state. The summit is also a great starting point for hikes, with several trails leading down the mountain.
• Jay Community Recreational Centre: This community hub offers a variety of outdoor sports facilities, including tennis courts, basketball courts, and a swimming pool. The center is a popular spot for locals and visitors alike, offering a chance to relax and enjoy some recreational activities in a friendly, laid-back environment. The center also hosts community events and activities, making it a great place to connect with locals.
• The Belfry: Located in nearby Montgomery, The Belfry is a cozy restaurant known for its hearty Vermont fare and welcoming atmosphere. The restaurant offers a menu filled with comfort food favorites, including burgers, steaks, and seafood, all made with fresh, locally sourced ingredients. The Belfry’s rustic charm and friendly service make it a great place to unwind after a day of exploring Jay and the surrounding area.

Good to Know

• Currency: The U.S. Dollar (USD) is the official currency. Credit cards are widely accepted, but it’s a good idea to carry some cash, especially in smaller towns.
• Transportation: While Route 100 is a scenic drive, a car is essential for exploring the area fully. Public transportation options are limited, so plan to rent a car or bring your own.
• Safety: Vermont is one of the safest states in the U.S., with low crime rates and a strong sense of community. Still, it’s always wise to take standard precautions and stay aware of your surroundings.

Getting There

• By Air: The closest major airport is Burlington International Airport (BTV), located about an hour’s drive from Waterbury. For those starting from the southern end of Route 100, Albany International Airport (ALB) is a convenient option.
• By Car: Route 100 runs the length of Vermont, making it easily accessible by car from neighboring states. If you’re flying in, renting a car is the best way to explore the route.
• By Train: Amtrak offers service to several towns near Route 100, including Rutland and Brattleboro, but you'll still need a car to fully experience the journey.

Best Time to Travel

The best time to travel Route 100 depends on what you want to experience. Fall (late September to October) is peak season for leaf peeping, with the foliage displaying stunning reds, oranges, and yellows. Summer (June to August) offers warm weather perfect for hiking, biking, and exploring the outdoors. Winter (December to March) is ideal for skiing, snowboarding, and other winter sports. Spring (April to June) brings blooming flowers and fewer tourists, making it a peaceful time to visit.

For Foodies

• Maple Syrup: Vermont is famous for its maple syrup, and no trip is complete without sampling this sweet treat. Visit a sugar house to see how it's made and pick up a bottle to take home.
• Cheddar Cheese: Vermont’s cheddar cheese is some of the best in the world. Stop by a local creamery to sample different varieties and learn about the cheese-making process.
• Craft Beer: Vermont has a booming craft beer scene, with breweries like The Alchemist, Lawson’s Finest Liquids, and Hill Farmstead Brewery leading the charge. Don’t miss the chance to sample some local brews.
• Apple Cider: Fresh apple cider is a staple in Vermont, especially in the fall. Stop by a cider mill to see how it's made and enjoy a glass of this refreshing drink, preferably with a cider donut on the side.

Route 100 in Vermont is more than just a road; it’s a journey through the heart of New England. Whether you’re exploring historic villages, hiking through scenic trails, or indulging in Vermont’s culinary delights, every stop along this route offers something special. So, take your time, enjoy the ride, and discover the charm of Vermont at your own pace. Safe travels! 🌲🚗🍁