Chester, Vermont. Depot street

7 Small Towns in Vermont to Visit for a Weekend Getaway

Vermont, a lovely state in the northeastern United States, is the epitome of natural scenery. Aptly nicknamed “The Green Mountain State,” one can find the massive Green Mountains running through the middle of the state. From rolling mountains to ski resorts, these mountains provide an endless array of fun for tourists visiting Vermont. Hidden within the beauty, the state’s small towns are perfect for a weekend of fun. Gorgeous views, delicious food, and friendly faces are just a few characteristics of these quaint retreats in Vermont. To this end, they are perfect for a relaxing weekend getaway with loads of fun.

Chester

The beautiful mountain town of Chester, Vermont.
The beautiful mountain town of Chester, Vermont.

Chester is a charming town hidden away in Windsor County’s Green Mountains. Surrounded by tall peaks and the Williams River, there is no end to the picturesque sights you can adore. That said, as you explore the town, you’ll notice that it is more than just natural allure. Originally chartered in 1754, Chester is a wellspring of historical value with iconic attractions. Visitors will rejoice at cultural attractions such as the Whiting Library, Country Girl Diner, and Sage Jewelry and Gifts. If you’re into books, head over to the 1892 Whiting Library, a trove of magnificent literature from old scriptures to e-books.

After a learning experience in the library, grab a bite at the rustic Country Girl Diner. Opened in 1966, it boasts an old-fashioned ambiance that goes well with the delicious pancakes and bacon! As your weekend comes to an end, stop by Sage Jewelry and Gifts, one of the town’s most famous shops. Here, you’ll find handmade glassware, artwork, gifts, and even jewelry for the perfect Vermont souvenir. That said, the best part of your weekend is sure to be the lovely conversations you have with Chester’s wonderful residents! All in all, it is a wonderful place to get away from urban stress and chill out.

Waitsfield

Aerial view of Waitsfield, Vermont.
Aerial view of Waitsfield, Vermont.

Two hours north of Chester lies the town of Waitsfield in Washington County. This scenic town rests within Green Mountain’s Mad River Valley, a stunning natural area split by the rapid Mad River. To this end, people from all over are drawn to Waitsfield for its natural beauty and outdoor activities. Just head over to the riverside and you can choose between swimming, boating, biking, and hiking to take in the views. Boasting a tranquil environment save for the sound of rushing water, it feels like you’ve entered a fantasy world. However, that’s not all. As winter rolls in, Waitsfield, similar to many of Vermont’s towns, becomes a wonderland for skiing. Skiers can drive 15 minutes to the Mad River Glen Ski Area, a wonderful ski area with 60 runs. Some of the most challenging terrain on the East Coast makes it a treat for experienced skiers.

Apart from Waitsfield’s natural beauty, the town itself has a lot to offer. Home to 1,850 residents, you’ll find friendly faces, great eateries, and fun establishments throughout. Art lovers can check out Artisans’ Gallery or Mad River Glass Gallery. Showcasing everything from handmade jewelry to intricate glassware, they are ideal weekend destinations. Or, have a relaxing evening at the Big Picture Theater & Cafe. As the name suggests, it is a lovely combination of movies and food with delicious maple donuts that can make any movie joyous. After exploring, retreat to the 1824 House Inn + Barn, a nearby hotel reminiscent of a rural farm.

Burke

Village of East Burke, Vermont.
Village of East Burke, Vermont.

If you enjoyed the winter fun of Waitsfield, Burke is another place you have to visit. Located along Burke Mountain, the town is a snowy paradise with endless skiing opportunities. Book a room at the Burke Mountain Resort for $150 and you can enjoy 55 runs of skiing and snowboarding. Speeding down 2,000 feet with 260 acres of skiable area is the perfect way to appreciate Vermont’s natural allure. In addition to this, snowmobiling, ice fishing, and snowshoeing are great ways to have fun in the snow. On the flip side, summers are just as fun with the expansive Darling State Park next door. With thick foliage, hiking trails, and picnic facilities, families will have a blast here.

After enjoying your days outdoors, retreat to Burke’s streets for a relaxing evening. Boasting a peaceful vibe bolstered by 1,650 residents, you can meet the friendly people in town. If you’re up for a conversation, drop by Mike’s Tiki Bar. With tons of locals, tourists, and chilled drinks, it is a great place to end your Vermont getaway.

Grafton

The Vermont Country Store at Christmas in Grafton, Vermont.
The Vermont Country Store at Christmas in Grafton, Vermont.

After Burke, head south to the quaint town of Grafton in Windham County. With a tight-knit community of 650 people, it exudes a towny vibe with friendly residents. As you roam through the streets, you’ll Grafton’s historic attractions and museums are sure to catch your eye. Boasting intricate stories, visitors are drawn to sites such as the Vermont Museum of Mining and Minerals, the Nature Museum at Grafton, and the Grafton Historical Society. Whether you are into exhibits on gemstones or stories about the Civil War, there is something for everyone in these cultural hotspots. If you want to take a piece of the culture home, Grafton features loads of gift stores and antiquity shops with great souvenir options.

Ode to its rural feel, the town has loads of green space ideal for outdoor fun. Nature enthusiasts can get straight into the greenery at Grafton Trails and Outdoor Center. 1200 acres of protected land make for an amazing environment where tourists can enjoy hiking, biking, swimming, skiing, and even fat biking. In addition, there are also summer camps and workshops where kids can have a blast! As the sun falls, head back to one of Grafton’s many cozy hotels such as Grafton Inn and Charming Inn Village.

Middlebury

Middlebury Falls in Middlebury, Vermont.
Middlebury Falls in Middlebury, Vermont.

Middlebury, another small town situated in the foothills of the Green Mountains, is an ideal destination for all types of adventurers. Home to a combination of history, food, and nature, one can choose how they want to spend their Vermont weekend. For example, if you’re interested in local culture, check out the Town Hall Theater or Mahaney Center for the Arts. From amazing plays at the theater to elegant artwork at Mahaney Center, these spots are a bundle of artistic creativity. Or, take a step back into the past with a visit to the Halpin Covered Bridge and Pump Mill Covered Bridge. Coveted by the Green Mountain’s verdant greenery, these bridges boast a rustic vibe reminiscent of the 1900s. These, coupled with the expansive Middlebury College campus make the town a boatload of fun for any weekend. That said, after spending the day out and about, you’ll likely be quite tired. So, end the day at one of the town's many breweries such as the fan favorite, Lincoln Peak Vineyard. Serving delicious spirits with a side of meat and cheese, one can relax and prepare for a good night’s sleep.

Manchester

A spooky Halloween display stands under stormy skies in Manchester, Vermont
A spooky Halloween display stands under stormy skies in Manchester, Vermont, via James Kirkikis / Shutterstock.com

After the interesting past of Middlebury, Manchester is a step up you must visit. Once a mining town with several iron deposits, Manchester developed rapidly through the 1800s. As mining died down in the following years, the town’s economy shifted to tourism boasting a unique combination of recreation and history. So, one can witness the intricate stories intertwined throughout the streets engulfed by historic architecture. Want to take a closer look? Stroll over to one of the town’s three historic districts bustling with rustic architecture and amazing destinations. Hildene, an 1800s mansion, was once a popular summer retreat for the affluent and was even used by the son of Abraham Lincoln. As of today, it stands in grandeur with personal items of the Lincoln family complimented with views of magnificent mountains. On the other hand, the American Museum of Fly Fishing offers a different take on the past. Filled with one of the world’s largest collection of items related to angling, it is a fisherman’s dream in Manchester. These, and dozens of other historic sites will make it feel like you’ve taken a step back in time.

While the historic is coveting, this former mining town is more than just the past. Smack dab in the heart of the Green Mountains, outdoor activities run hand in hand with Manchester. Want to take on the heights? Head over to Mount Equinox to conquer the 3-mile Red Gat Trail hike leading to its summit. As you reach the top, take a moment to adore the panoramic viewpoint to appreciate Vermont’s wilderness. However, make sure you have the right gear and some experience as the 2,800 feet climb is a tasking endeavor. If this isn’t your cup of tea, opt for the tranquil Equinox Pond instead. A picture of calm and composed, this pond boasts clear waters lined with thick foliage for an amazing environment. The nearby areas are also ideal camping spots where one can enjoy the night sky in Vermont’s fresh air. With so much to see and do, you might not want to leave Manchester when the weekend ends.

Stowe

Aerial view of Stowe, Vermont.
Aerial view of Stowe, Vermont.

Stowe is a lovely retreat that fits the bill for a weekend in Vermont. Nicknamed “the Ski Capital of the East,” this town is home to the wonderful Stowe Mountain Resort. The resort is a bundle of winter activities spanning both Mount Mansfield and Spruce Peak. So, choose between 100+ runs of all skill levels as you cut through the 485-acre ski area. Moreover, with 12 lifts, getting back up is a breeze so skiers can focus on their technique and the surrounding wilderness. As the snow starts to melt, a new side of Stowe’s natural beauty comes out of hiding. With amazing destinations such as the Stowe Recreation Path and Moss Glen Falls, tourists tend to be in awe of Mother Nature’s allure. So, whether you’re a hiking enthusiast, skier, or just want to check out a cool waterfall, Stowe has got you covered.

Bolstered by its beautiful sights, the town itself is a hub of tourist recreation. Festivals, shopping, eating, and art are just a few ways that the community comes together. If you want to meet some of the 5,200 locals, grab a seat at the Alchemist Brewery. Featuring unique architecture coupled with great drinks, conversations flow in this establishment. After all the fun, book a room at the Stowe Village Inn for a comfortable night’s stay throughout your weekend.

No matter what you’re looking for on a weekend getaway, Vermont is sure to be a blast. Whether it is with the endless scenery of Waitsfield or the interesting stories at Manchester, there is something for everyone. To top it off, each town is astray from the troubles of urban living so adventurers can focus on having the best time! So, what are you waiting for? Book your hotels and head out to “The Green Mountain State” for a great weekend getaway!

Share
  1. Home
  2. Places
  3. Cities
  4. 7 Small Towns in Vermont to Visit for a Weekend Getaway

More in Places