23 Best Day Trips & Small Towns in Vermont

By VI Staff on August 21, 2020 - Updated

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Vermont tends to bring to mind maple syrup and remote ski resorts, but that's only the beginning of what this wonderful state has to offer. There's an excellent selection of places to visit, but the state's peaceful back roads and beautiful fall foliage make for a beautiful day trip no matter where you choose to go. Head to the secluded Lake Willoughby for a relaxing day in nature or drive up into the Green Mountains to ski, hike, or mountain bike. If you're interested in history, take a tour of Hildene, the former summer home of Abraham Lincoln's son. CDC information for travelers. Hours/availability may have changed.

1.Bennington

Boasting a vibrant arts community, a rich history, and easy access to outdoor recreation, Bennington offers everything you'd want from a small Vermont town. The charming Main Street is lined with sidewalk cafes and locally-owned boutique shops, and if you head over to the downtown Arts District, you'll find galleries, a theater, and outdoor performance venues. History buffs should also visit the Bennington Battle Monument, a stone obelisk that happens to be the tallest man-made structure in the state. Just outside town, you can hike the steep but worthwhile 3.6-mile Harmon Hill Trail to get fantastic views of Bennington and the surrounding area.

2.Burke

Tucked away in Vermont's gorgeous "Northeast Kingdom", an area that was once chosen by National Geographic as part of their geotourism program, the tiny town of Burke is a true outdoor playground. Every season offers something unique to do; winter brings the opportunity to ski, snowmobile, and ice climb, while the warm summer weather is perfect for hiking, mountain biking, golfing, and paddling down the Clyde River. Spring is the perfect time to learn about the process of making maple syrup, but autumn is perhaps the most spectacular season, and visitors flock from all over the state to marvel at the incredibly colorful fall foliage.

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3.Chester

A picturesque town hidden away in the Green Mountains, Chester is one of Vermont's best-kept secrets. The town is best known for its unique "stone village", a collection of pre-Civil War homes made from local granite, which is listed on the National Register of Historic Places. After you've seen the stone village, the Chester Village Historic District is only a few blocks away, and here you'll find an assortment of stately Federal and Victorian style buildings that house boutique shops. If you're visiting in September, you might be here for the annual Fall Craft Festival, when artists sell their wares in the village green.

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4.Dorset

Named after the beautiful Dorset county in England, Dorset is a quintessential New England town that was established in 1761. Several of the businesses in town have been operating continuously since the town was founded, including the Dorset Union Store and the iconic Dorset Inn. The small downtown shops sell locally made handicrafts, including quilts and custom wooden signs, and a farmer's market is held every Sunday all throughout the year. The town is also home to the oldest marble quarry in the entire country, which is now a popular local swimming hole during the summer.

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5.Grafton

With its lovely clapboard houses and its white steeple church, Grafton is an inviting little town that looks like something straight out of a movie. In fact, it looks much like it did back in the 1800s; many of the historic buildings have been carefully and lovingly restored by the community, but unlike some other "museum towns", it's home to an active community of residents. Visitors often come here simply to soak in the atmosphere and browse the town's art galleries and shops, but another popular attraction is the Grafton Cheese Co., which sells delicious hand-crafted cheeses.

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6.Hartford

Located at the confluence of the Connecticut River and the White River, Hartford is composed of five villages, each with a distinct character. All of the villages are worth a visit, but the highlights include Quechee, an appealing resort town full of beautiful historic buildings, and the rural West Hartford, which offers excellent fishing and is located on the Appalachian Trail. The surrounding area boasts plenty of wonderful attractions as well, including the spectacular 165-foot Quechee Gorge and local maple farms where visitors can learn about how maple sap is collected and turned into syrup.

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7.Hildene

The former summer home of Robert Lincoln, Abraham Lincoln's son, Hildene is a beautiful Georgian Revival mansion surrounded by landscaped gardens. The mansion is the highlight of the property, but other features include a sustainable goat dairy farm, a restored Pullman car, and a network of walking trails. Guided tours of the house and property are available on a seasonal basis, but staff are always available to answer questions even when tours aren't being held. Visitors who want to learn even more about the site can book a special behind-the-scenes tour that goes into some of the archive rooms and the Exhibit Prep Room.

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8.Killington

If you want to ski, hike, or golf, Killington is one of the best destinations in the area. Located in the Green Mountains, the town is home to both the Pico Mountain ski resort and the Killington ski resort, which is the largest ski area in New England. Both resorts offer trails for skiers and snowboarders of every ability level, and in the summer, these trails are perfectly suited to hiking and mountain biking. Other attractions in the area include the Green Mountain National Golf Course, the beautiful Thundering Falls, and the President Calvin Coolidge State Historic Site.

9.Lake Willoughby

Lake Willoughby isn't as well-known as some of the other lakes in Vermont, but that's exactly why it's so appealing. It's not the place to come if you're looking for big-city amenities; the only town you'll find on the lakeshore is the tiny community of Westmore, which has little to offer besides a few small stores selling basic supplies. Instead, visitors come here to enjoy the public beach, take advantage of the lake's excellent fishing, and hike through Willoughby State Forest on the lake's southern end. If you want to see the lake from above, you can climb up Mount Pisgah for some wonderful views.

10.Lincoln

Sitting at the base of Mount Abraham, the town of Lincoln is a lovely little spot known for its rural character and its beautiful natural surroundings. It was established in 1780, and contrary to what you might expect, it wasn't named after Abraham Lincoln but rather a general who served in the Revolutionary War. The village center is small but welcoming, and although it features a charming church and a handful of shops, the real attractions are found in the surrounding area. Many visitors choose to hike up Mount Abraham, and the Mad River Glen and Sugarbush ski areas are only half an hour away.

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11.Manchester

One of the most popular vacation destinations in Vermont, Manchester offers an enticing blend of outdoor beauty, quaint boutique shops, and rich history. It's a popular tourist destination year-round, but it's at its most spectacular in the fall, when the fall foliage puts on a colorful display. Spring and summer bring the opportunity to golf, fish, and browse farmer's markets, and during the winter, you can skate on the Riley Rink at Hunter Park, tour the historic Lincoln family estate Hildene on snowshoes, or take a cozy horse-drawn sleigh ride on one of the local farms.

12.Middlebury

Set on the banks of the meandering Otter Creek, Middlebury is a historic community with a college town feel. The streets are lined with stately brick buildings and boutique shops selling everything from jazz records to locally made wooden toys, and the surrounding area offers the opportunity to hike, fish, and cycle. If you'd like to combine culture with the great outdoors, take the Robert Frost Interpretive Trail, which commemorates the poet's work and life with interpretive plaques. The town is also the proud home of the Middlebury Tasting Trail, a route that brings visitors to the best local cideries, breweries, wineries, and distilleries.

13.Montpelier

With a population of less than 8,000, Montpelier is the smallest state capital in the entire country, but don't let that dissuade you from paying it a visit. It offers an astonishing number of attractions despite its small size, including family-run maple sugarhouses, the elegant gold-domed Vermont State House, and the Lost Nation Theater, which is a unique establishment committed to hosting only plays about the positive side of human interaction. After seeing the sights, there are plenty of places to kick up your feet and relax as well, including cozy cafes and inviting wine tasting rooms.

14.Peacham

Known for the stunning show put on by the area's foliage in the fall, Peacham is said to be the most photographed town in all of Vermont. The town is surrounded by a handful of beautiful state parks that offer all sorts of opportunities for hiking, fishing, and mountain biking, and a farmer's market is held on the Peacham Academy Green every Thursday during the summer. For a true taste of the local lifestyle before you leave town, stop by the friendly Peacham cafe to enjoy an excellent cup of coffee or a meal made with locally-sourced ingredients.

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15.Reading

Located in Windsor County in eastern Vermont, Reading is a peaceful, family-friendly destination that welcomes visitors who want to relax and enjoy the beautiful surroundings. The biggest tourist attraction in the town is the gorgeous Jenne Farm, an incredibly photogenic spot that was used as a backdrop for the movie Forrest Gump. The farm is not open to tourists, but there's a popular viewpoint where you can take photos and marvel at the scenery. Other points of interest in the area include the historic markers known as the Indian Stones, the picturesque Bowers Covered Bridge, and the Hall Art Foundation,

16.Rutland

Nestled in the heart of Rutland County, the city of Rutland boasts an excellent assortment of interesting things to see and do. The historic downtown is home to unique boutique shops and restaurants serving up delightful dishes made with locally sourced ingredients, and if you're interested in architecture, you'll also enjoy the opportunity to see more than 100 houses listed on the National Register of Historic Places. There is also a Saturday farmer's market that runs all throughout the year, and if you want to add some nature to your day, you can stop at the beautiful Rutland Falls just outside town.

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17.Shelburne

Situated on the shore of Lake Champlain, Shelburne is technically a suburb of Burlington, but it offers much more of a small-town feel. Many of the attractions here are agricultural in nature; visitors can stroll through the charming Shelburne Farms and learn about sustainable farming practices, go apple picking at Shelburne Orchards, or taste the award-winning wines at Shelburne Vineyards. If you're traveling with kids, you can also attend a children's read-along at the Flying Pig Bookstore or stop by the Vermont Teddy Bear Factory to tour the facilities and design your own teddy bear.

18.Stowe

Set at the foot of Mount Mansfield, the tallest peak in the state, Stowe is best known for its incredible downhill and cross-country skiing. There's no denying that the area is an exceptionally beautiful wonderland during the winter months, but the other seasons are just as lovely, and summer brings the opportunity to hike and cycle while fall ushers in a colorful display of leaves. Most visitors come here for the nature, but the 200-year-old resort town is worth a visit in and of itself, and it boasts a fantastic selection of locally owned shops, craft breweries, restaurants, and spas.

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19.Waitsfield

Thanks to its location along the Scenic Route 100 Byway, Waitsfield is perfectly suited to a day trip. It offers jaw-dropping views of the Mad River Valley and the surrounding mountains, but the biggest reason to come here is the nearby Mad River Glen Ski Area, which offers wonderfully challenging skiing in the winter. Unlike many other ski resorts in the area, this one doesn't permit snowboarders. If you don't ski, there are still plenty of things to do, with highlights including the historic Skinner Barn, the Waitsfield Covered Bridge, and the Big Picture Café and Theater, which shows several movies daily.

20.Warren

Warren is the only other town besides Waitsfield in the Mad River Valley, and although its slightly larger than its sister town, it tends to draw visitors who are interested in the surrounding nature rather than in the town itself. However, there are still more than enough amenities, including a handful of restaurants and a general store selling everything from freshly baked scones to handmade scarves. Outside the town, your choice of activities will vary depending on the season, but popular options include skiing, mountain biking, and watching the sun go down at Sunset Rock.

21.Waterbury

Conveniently located in the center of Vermont at the convergence of Interstate 89 and the Scenic Route 100 Byway, Waterbury is a quaint little town full of craft breweries, eclectic shops, and historic homes. The town is famously home to the Ben & Jerry's factory, and visitors are welcome to stop by for tour of the facilities and a scoop of delicious ice cream. If you'd rather enjoy the beautiful nature surrounding the town, you can hike up the imposing Camel's Hump, go for a refreshing swim in the Winooski River, or cycle along the Stowe recreation path.

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22.Weston

Another tiny town in Windsor County, Weston embodies the best of everything Vermont has to offer. The town is a mecca for skiers in the winter, as it offers access to no fewer than four downhill ski areas, but it's a charming place to visit no matter what the time of year. Visitors can catch a show at the Weston Playhouse, golf at the Okemo Mountain Resort, or relax in the village green. It's also a wonderfully unique shopping destination, and visitors can browse the aisles at the rural Vermont Country Store or get in a festive spirit at the Weston Village Christmas Shop.

23.Woodstock

Although it's not as well-known as the New York town that hosted the iconic 1969 music festival, Woodstock is a marvelous place to visit if you're interested in natural beauty and rural culture. The town is surrounded by opportunities to hike, mountain bike, and ski, and the village itself is full of local artisans and craftspeople selling their wares. While you're here, you can also take pictures of the town's three historic covered bridges, visit the Billings Farm and Museum to watch hands-on farming demonstrations, or tour the elegant Victorian mansion in the Marsh-Billings-Rockefeller National Historical Park.