If you’re looking to travel to towns that are quaint, but cool, picturesque, yet hip, relaxed, but still very, very active, then Vermont is the perfect destination for you! Between the incredible hiking, the spectacular skiing, and the fabulous fall foliage that attracts thousands of tourists known as “leaf peepers” every year, Vermont has a LOT to offer its visitors; check out this list of the best places to visit in Vermont so you can see for yourself what makes Vermont the quirky, cool, fun-loving state that it is!
Oh, and if you’re looking for things to do in Vermont this weekend or what to do in Vermont today, check out this Vermont events calendar to figure out what’s happening in the Green Mountain State during your visit!
Best Places to Visit in Vermont
With a population of less than 5,000, Manchester has the Classic Vermont small-town vibe! You’ll experience the quintessential New England aesthetic with its prominently situated white-steepled church and carefully tended historic Main Street, phenomenal local restaurants, charming inns and B&Bs (check out The Reluctant Panther, the perfect spot for a romantic getaway in Vermont!)
There are plenty of fun things to do and sights to see in Manchester, like Hildene, the Lincoln Family Home, the home and gardens of the only son of President Abraham Lincoln to make it to adulthood, and outdoor activities like waterfall hikes. If you’re looking for indoor activities, the Manchester Designer Outlets were named “One of the Top Shopping Getaways in New England” by Yankee Magazine. Manchester is a great Vermont town to visit any time of year!
One of the cutest small towns in Vermont, Bennington has plenty of fun outdoor things to do, like hiking Bald Mountain. You’ll get all those quintessential Vermont views like streams, wildflowers, and once you reach the top, incredible scenic vistas. If you’d rather get out on the water, go kayaking at nearby Lake Paran. If you’d rather explore town, there’s plenty there for you too!
Visit the Bennington Museum, then the Bennington Battle Monument, the 300+ feet high monument that draws in tourists from all around. There’s nothing quite like the view from the top! There are lots of great restaurants in Bennington, too, but be sure to swing by The Apple Barn during your visit to this VT town to sample some of their apple cider and cider donuts… if you’re wanting an authentic taste of Vermont, this is the perfect way to get it!
Not only has Brattleboro been named one of the top 10 small art towns in the US, but this cute VT town has some fairly unique claims to fame: The Strolling of the Heifers is a non-profit organization that facilitates local farm to table connections, and their annual event includes a literal parade of actual heifers adorned with flower garlands that stroll along the route, promoting a local connection between farmers and community. Brattleboro is also home to the New England Center for Circus Arts (so basically, the circus is ALWAYS in town) and hosts several festivals throughout the year.
Brattleboro has a little bit of everything to make a Vermont visit sing: unique, independent (and delicious!) restaurants and breweries, indie bookstores like Everyone’s Books, with the slogan “raising hell since 1984,” farmer’s markets, museums, art galleries, and a lovely covered bridge that is basically begging to be photographed. There’s always something to see and do in Brattleboro, so be sure to add it to the list of must visit places in Vermont!
Of course, the state capital is going to end up on a list of the best places to visit in VT! There are plenty of interesting things to see and do in Montpelier, including museums like the Vermont Historical Society Museum and the Vermont Granite Museum, and architectural gems like the Vermont State House, open to the public Monday through Friday, with interesting features like the statue of Ceres, the goddess of agriculture, that sits atop the golden dome roof.
There’s art and culture, excellent restaurants and places to stay, a gorgeous covered bridge, hiking, and in true Vermont fashion, a couple of sugar houses where you can tour and see for yourself how maple syrup is produced in Vermont! Montpelier is definitely one of the top must visit places in Vermont.
Ah, Stowe! One of Vermont’s best towns to visit, Stowe is considered one of “America’s Best Ski Towns,” but this tiny town has more going on than just its big hills! There are gorgeous hiking trails to explore, like Moss Glen Falls and Mount Mansfield, and the Trapp Family Lodge (Yes, the inspiration of The Sound of Music!) and Stowe Mountain Resort offer four-season outdoor and indoor activities.
Stowe is also home to some of the most fantastic resorts and spas in New England. Stoweflake offers lush accommodations and spectacular spa services and was even named one of the “Best in the World” by Conde Nast Traveler in 2009, then there’s Topnotch Resort, the epitome of alpine elegance, luxury, and comfort, with lavish accommodations and a full-service spa. In addition to all the great places to stay in Stowe, there are tons of great options for food and drink, too; check out some of these great breakfast spots! Stowe is a wonderful winter destination, sure, but any time of the year, Stowe will not disappoint!
While Killington is most popularly known for its namesake, Mount Killington, this Vermont town has more going on than just fun on the mountain! Killington Resort is probably the most popular place to go because the 2000 skiable acres are what pulls most visitors out to Killington, but there are other ways to have fun on The Beast of the East! During the warmer weather months you can take scenic gondola rides, play a round at the Killington Resort golf course, and take a ride on the Beast Mountain Coaster!
Gifford Woods State Park and Thundering Brook Falls are both popular places in Killington to get out and enjoy the scenery, and if you’re looking for something to do indoors, get your relax on at Spa at the Woods before grabbing a table at Liquid Art Coffeehouse & Eatery, where you get to sample local art and music along with the delicious food and drink offerings. For a cool Killington place to stay, book a room at Killington Grand Resort Hotel to access their year-round 75 foot heated outdoor pool, hot tubs, a firepit, and onsite restaurants right in the heart of Killington Resort!
Beautiful Burlington is Vermont’s largest city (although it doesn’t take much to earn that title in a state known for its quaint little towns!) and is progressive, hip, and vibrant. There is just So. Much. To. Do in Burlington! Visit Church Street, get a scoop of Ben & Jerry’s just right up the street from the original Ben & Jerry’s, travel on the famed Burlington Bike Path, head off on a hike, and enjoy the views of lovely Lake Champlain.
Another fun thing about Burlington? Come HUNGRY! Yes, farm-to-table is pretty much a given across most of VT, and Burlington takes that and runs with it. Whether you’re looking for the perfect coffee shop, breakfast place, brewery or restaurant, there’s always something sure to satisfy in Burlington.
Burlington is also home to awesome hotels and inns, and cool Airbnb options. Regardless of where you choose to stay, your visit to Burlington will show you what makes Burlington, Vermont so… well, so Vermont with all the independent shops and eateries, the incredible arts scene, and the cohesive sense of community.
Grand Isle (South Hero Island)
The biggest island in the Vermont Champlain Islands, Grand Isle is also often referred to as South Hero island, for the popular town of South Hero. There are plenty of fun things to do on this Vermont island, including hiking in Grand Isle State Park, or horseback riding at Breakaway Farm.
One of the most popular things to do on Grand Isle is to visit Snow Farm Vineyard, one of the most popular wineries in all of New England. Snow Farm Vineyard hosts a variety of events throughout the year, including concerts, culinary events, festivals, and more. South Hero Island is definitely one of the top places to visit in Vermont.
Another adorable small town to add to your Must Visit in Vermont list, Rutland has an interesting claim to fame- its Rutland Daily Herald is the oldest newspaper in VT, having been continuously published since 1794! Rutland is also home to an adorable downtown with a great art scene, including several incredible murals and a neat Sculpture Trail that are downtown!
Spend some time hanging at Lake Bomoseen, hiking at some of the popular trails near Rutland like Bald Mountain Trail and the White Rocks Recreation Area Trail, and relaxing in the Himalayan Salt Cave at the Pyramid Holistic Wellness Center. Plus, Killington is less than a half hour drive, so there’s plenty to do and see both in and near Rutland VT!
Woodstock has been lauded as being one of the most beautiful small towns in America, and it is probably one of the most picturesque towns in the country, for sure. In fact, come Christmastime, it is one of those towns that look like they are straight out of a Hallmark movie! There are so many great things to do in Woodstock, like hiking, visiting the Marsh-Billings-Rockefeller National Historical Park, and walking the charming Woodstock streets. Be sure to visit F.H. Gillingham & Sons, the general store that has been in Woodstock since 1886 and offers one-of-a-kind specialty gifts for any occasion.
With quintessential covered bridges and unique experiences, like staying at Fat Sheep Farm, Woodstock is a very cool small town in VT to visit. There are plenty of great places to stay in Woodstock, but if you’re wanting to go all out, check out Woodstock Inn and Resort. Yes, it is a splurge, but with the tagline, “Vermont’s Most Beautiful Address,” it lives up to this reputation. Woodstock is lovely any time of the year, but during the winter months many use Woodstock as a home base for their skiing adventures, and Woodstock’s Wassail Weekend is a fabulous way to herald in the Christmas season. When looking for the perfect Vermont vacation destination, Woodstock has absolutely got to be at the top of the list!
Beautiful Vermont is definitely a must-visit New England state; just driving through the state on the scenic byways is a must-do! Fun, kind of quirky, but always cool, any of these places to visit in Vermont would make for an excellent vacation destination.
Read these next:
- The Perfect Vermont Road Trip: 5-7 Day Itinerary
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- Top 5 Places to go Dog Sledding in Vermont
- 15 Best Places to Visit in New England: The Top Vacation Spots
- 10 Fun Things to do in Vermont with Kids
Amy is the founder of New England with love. A proud Vermonter, she hopes to share her love of New England and help you find the best adventures in the region. Amy is also blogger/founder at Two Drifters, where she writes alongside her husband about romantic and couples travel, relationships, honeymoons, and more. When not working on websites, Amy is probably reading, cuddling with her husband, son, and cats, & drinking a maple latte.