8 Coolest Vermont Towns For A Summer Vacation In 2025

Blanketed in forests and accentuated by pristine lakes and rivers, Vermont’s vistas resemble a postcard sent home from summer sleepaway camp. In a way, the Green Mountain State has become a sort of playground for adults and families to reinvent that nostalgic camp experience with endless outdoor activities like hiking, canoeing, and swimming. In fact, over 5 million people make the voyage to the state each summer to savor its inviting towns’ community festivals, off-the-beaten-path nature areas, and old-fashioned farms and orchards. From hot air balloons taking flight in Woodstock to river kayaking in Middlebury, if you are contemplating spending your summer vacation in Vermont, these eight towns would be perfect for a New England holiday.

Bennington

“Two roads diverged in a yellow wood,” and you chose the one that leads to Bennington, the Green Mountain State’s first established town. There’s a lot to love about this town in southern Vermont, and summertime especially allows it to put its best foot forward.

Literature lovers will be excited to visit the Robert Frost Stone House Museum, the poet’s residence for almost a decade in the early 1900s. There, you can learn more about Frost’s life and poetry before heading to Old Bennington to visit his gravesite. To round out your Frost foray, hike down the Robert Frost trail to bask in nature’s allure, a central theme of his work. You’ll pass through farmland once owned by Frost, where he wrote his beloved poem, “Stopping by Woods on a Snowy Evening.”

Another of Bennington’s standout features is its championship-rated golf course at the Mount Anthony Country Club. Backdropped by expansive views of the Green Mountains, this course is great for players of all experience levels—just don’t let Vermont’s verdant beauty get in the way of your swing!

Labor Day weekend is a popular time to vacation in Bennington because that is when the town transforms into Garlic Town, USA. A homage to all things garlic, the community invites residents and tourists to “eat, drink, and get stinky.” There, you can taste garlic bread, garlic bacon, and even garlic fudge. In 2024, these interesting and often daring flavor combinations attracted over 10,000 attendees to the celebration of the pungent bulb that shines in Vermont’s cool climate.

Middlebury

Once a Vermont marble mecca and Morgan horse breeding base, the Middlebury of today still brims with the innovative spirit of the past. Flanked by the liberal arts college of the same name, Middlebury boasts storybook beauty. Think: white-steepled churches, a charming Main Street, and a literal waterfall crashing through the town’s center.

The town’s magic really comes alive in the summer months. Hikers will love exploring the Trail Around Middlebury, or the TAM, as the locals call it. This 18-mile footpath circles around the entire village and connects various landmarks and important conserved areas. After your hike, find a swimming hole to cool off—it’s essentially a Vermonter rite of passage. You’ll love Middlebury Gorge for its waterfall cascades and clear waters. Or, rent a kayak from Green Mountain Adventures and enjoy a leisurely trip down Otter Creek. Don’t be fooled by its misleading name; it’s actually Vermont’s longest river, running for 112 miles.

Middlebury also features a number of summertime festivals for visitors to enjoy. The long-running Festival on the Green is a favorite July event that features a week-long concert lineup right in the middle of downtown. August welcomes both Foodaroo, a celebration of local culinary creatives vending their tasty food and beverages, and the New Filmmakers Festival, an event focused on fresh voices from around the world in independent film.

Burlington

Sitting on the waterside of Lake Champlain, Burlington, the state’s most populous city, is a summertime dream come true. If you’re in town on a Friday evening, make like a local and head to the South End Get Down, a kid- and dog-friendly event with the energy of a neighborhood block party, complete with live DJs, food trucks, and a beer garden. Running from May to September, locals have chosen the Get Down as a “Best of Vermont” event for three years running.

You could also spend an easygoing day exploring Burlington’s red-bricked Church Street Marketplace. Mornings call for coffee and a bagel from Burlington Bagel Bakery, a town institution since 1979. For shopping, continue on the rainbow-flagged pedestrian walkway for an assembly of unique boutiques perfect for finding a souvenir from your Vermont getaway. Check out Flora & Fauna for botanical-inspired gifts or Golden Hour for a handmade token. When it’s time for lunch, the outdoor dining spot Leunig’s Bistro, a French restaurant with fabulous food and ambiance, will delight you with an afternoon meal, people watching, and live music.

A trip to Burlington would not be complete without taking advantage of Lake Champlain, also called the Sixth Great Lake for its tremendous size and gorgeous waters. You can stroll along the Burlington Greenway, an eight-mile path that runs alongside the lake from south to north, or book a boat tour with Cruise Lake Champlain, a family-owned operation, with the mantra “the best things in life aren’t things.” The experience of a sunny trip to Burlington proves that to be true.

Newport

Originally coined by Governor George Aiken in a political speech, the northeast region of Vermont is lovingly referred to as the Northeast Kingdom, or simply “The Kingdom” by locals. And within this region’s regal beauty lies the city of Newport, a crown jewel of New England, founded on the southern shores of Lake Memphremagog.

Each year, apple orchards produce a million bushels of Vermont’s state fruit. For a quintessential Newport encounter, you’ll love visiting the Eden Specialty Ciders tasting room for a glimpse into how their homegrown apple varieties are transformed into hard ciders. If you make a reservation, you can tour the facility and even enjoy a private tasting. Afterwards, wander down the town’s enchanting Main Street for a yummy meal at Dusit Thai Cuisine or Lago Trattoria.

To get outdoors in Newport, head to Bluffside Farm, a private farm purchased by the Vermont Land Trust in 2015 and, thanks to community brainstorming, completely reimagined as a one-of-a-kind public and protected recreational area. True to its origins, there’s a community garden where residents can grow their own vegetables. But, there’s also a mile of sandy beach, terrain that is very unique to Vermont. The woodlands are also a great place to observe wildlife and identify interesting plant species. There’s even a mile-long newly constructed trail and boardwalk that now links up with an existing trail system, taking you all the way to the Canadian border.

Woodstock

Woodstock is a darling rural town on the banks of the Ottauquechee River in central Vermont. With a population of around 3,000 people, this small town values what’s homegrown and handmade, and you’ll quickly see that the farmers, artisans, and independent sellers are the beating heart of this tight-knit community.

Your summer vacation in Woodstock kicks off with the annual Quechee Balloon Festival, a weekend event where dozens of hot air balloons take to the skies, creating a mesmerizing display of lofty colors. As the longest-running hot air balloon festival in New England, this is a tradition that folks from Woodstock hold dear.

Woodstock is also a great place to try your hand at fly fishing. Through the Woodstock Inn & Resort’s program, Orvis-endorsed guides will help you learn to flycast before heading out to a local waterway or river of your choosing. Since the excursion can be customized, anglers of all experience levels will have fun getting out in the water to see what bites, of course, with experts on standby to assist if necessary.

Also, the town is home to a number of family-run farms where you can shop for the finest local ingredients like award-winning cheeses from the Vermont Farmstead Cheese Company. Or, plan a trip to Sugarbush Farm, where you can learn how maple syrup is made, walk amongst the tall maple trees, and sample an array of cheeses, jams, and mustards. The weekly Market on the Green is another way to peruse the produce and handmade goods sold by local growers and artisans that form the foundation of Woodstock life.

Waterbury

Located in Central Vermont, Waterbury is another dreamy vacation spot deep in the Green Mountains. With lively community events, an intriguing food scene, and plenty of outdoor recreational activities, Waterbury ranks high on the summer fun meter.

Each July, the town gathers for the Waterbury Arts Fest, which turns the historic downtown into an outdoor art gallery and street fair. With over 100 exhibiting artisans, live music, food trucks, and special activities for the kids, this full-of-spirit fête will expertly acquaint you with the small town’s creative vibe.

Waterbury has crept into the culinary spotlight over the years, becoming one of Vermont’s key destinations for food lovers. With the motto of “feast local,” the town champions its independent eateries, like the cozy Hen of the Wood restaurant—its rotating menu is a great representation of Vermont ingredients found only miles from the restaurant itself. Waterbury has also emerged as a haven for craft beverage makers and tasters with an assortment of breweries, distilleries, and cideries for visitors to try. Prohibition Pig is a great place to start for house-made beer and barbeque.

When the temperatures rise, the Waterbury Center State Park is the place to be. This 90-acre peninsula surrounded by the Waterbury Reservoir is a guaranteed day of family fun. Beaches along the reservoir provide perfect spots for swimming, picnicking, and grilling. Thanks to clearly marked no-wake zones, swimmers can easily share the water with boaters. And for those who want to sleep under the stars, the nearby Little River State Park has campsites available to reserve overnight.

St. Albans

In 1983, Ben & Jerry’s built the world’s largest ice cream sundae right in St. Albans. Weighing in at 27,102 pounds, this massive dessert underscored what summertime in the small town is all about: sweet, unadulterated bliss.

Start with a tour of St. Albans’ downtown district. Anchored by the immense Taylor Park, this area of town is filled with charming shops like Rail City Market for Vermont specialty foods or The Eloquent Page, a classic bookstore suitable for any bibliophile. Later, hop over to St. Albans Bay Marina for lunch at Bayside Pavilion. With stunning views of Lake Champlain and delicious cocktails, you’ll sink into your vacation just a little bit more.

For a really unique day trip, take the passenger ferry from the gateway Kill Kare State Park to Burton Island State Park, located in Lake Champlain’s Inland Sea. Since Burton Island is semi-remote and only accessible by boat, it’s perfect for really getting away from noise and into nature. Because no cars are allowed on the island, you are free to explore every inch of the shoreline and interior land. There’s also a nature center where you can learn about the plant and animal species that make Burton Island home, and if you want to get out on the water, the park offers kayak, canoe, or stand-up paddleboard rentals. At the end of the day, hike the North Shore Trail to catch a signature Lake Champlain sunset.

South Hero

Tucked into the Champlain Islands, South Hero is Vermont’s best-kept summer secret. While small, it is full of extraordinary places that will punctuate your special vacation.

First, Snow Farm Vineyard & Distillery is a must-see stop in South Hero. The Tasting Room onsite allows you to sample a multitude of unique varietals, and there are ample outdoor areas to kick back and relax with a glass of your favorite offering. Throughout the summer, you can catch live music from the deck or take a self-guided tour throughout the farm’s 140 acres.

You’ll also find many adorable farms and orchards to visit on South Hero. Allenholm Farm is Vermont’s oldest commercial apple orchard and has become famous for its maple creemees and vanilla soft-serve ice cream doused with pure maple syrup. Hackett’s Orchard features other delicacies like cider donuts and cider slushes, and starting in late July, you can pick your own apples when the first varieties ripen.

When in South Hero, be sure to take a stroll through the whimsical Birdhouse Forest, an absolutely enchanting marshland right next to White’s Beach. In an effort to rid the area of a pesky mosquito overpopulation, the owners of the land put up a handful of brightly-colored birdhouses to encourage swallows to settle in for a mosquito feast. Years later, there are around 800 bird houses hanging from the trees, and most of them are occupied! You’ll also find a good number of wooden dinosaurs placed throughout the forest for good measure; the owner happens to be a very handy woodworker.

Spend Summer in Vermont

You won’t have to pass a swim test or compete in Color Wars, but a Vermont vacation is the closest you can get to recreating a childhood summer camp in the great outdoors. In all four corners, the state provides idyllic landscapes, incredible recreation opportunities, and winsome residents ready to welcome you to their home. So, whether you want to sample a smorgasbord of Vermont food staples, dive into a popular swimming hole, or stroll along the shores of Lake Champlain, these eight towns are the best for enjoying Vermont summers. Just don’t forget to call the top bunk!