9 Old-World Towns to Visit in Vermont
Ever feel like your to-do list is a marathon and your inbox is a never-ending sprint? The state of Vermont might just be the answer to your frantic lifestyle. Here, “hurry up” is replaced with “take your time,” and locals might give you a strange look if you ask them where the nearest express lane is. Historically, this state has held much significance for the United States as a whole. It even was the first to outlaw slavery in 1777, setting an example for the rest of the nation. Its mountainous geography is also part of its charm—rising peaks like Mount Mansfield (the highest in Vermont) make the Green Mountains an outdoor playground with great hiking and skiing. Start searching for flights now because Vermont’s small towns are calling your name, and these nine destinations have the loudest voices.
Middlebury
Middlebury may not be the first place you think of when planning a getaway, but this town’s charm is the sort that grows on you like a good Vermont cheddar. Founded in 1761, the town is steeped in colonial history, not least because it’s home to Middlebury College, a prestigious institution that’s been shaping minds since 1800. If you are a fan of old-school educational architecture, the campus is filled with historic buildings that will make any lover of classic college campuses swoon. Meanwhile, the Henry Sheldon Museum is a goldmine of Vermont artifacts that tell stories from the state's early days. During your stay, book a room at the Middlebury Inn, which first opened in 1827 and grants a dose of old-world hospitality with all the modern comforts you need. On the other hand, Otter Creek, Vermont’s longest river, runs right through town and welcomes adventurers for kayaking and canoeing.
St. Johnsbury
The Fairbanks Museum and Planetarium, built in 1891, is a must-see for anyone who visits St. Johnsbury—it has been educating visitors with scientific exhibits for over a century, while its planetarium dazzles both adult and child minds with glimpses of the stars. For a taste of art and history, head over to the St. Johnsbury Athenaeum, a library built in 1871 that doubles as an art gallery, with works by the Hudson River School painters hanging on its walls. Moreover, St. Johnsbury has deep roots in railroads, with the St. Johnsbury and Lamoille County Railroad serving as a key transport link during the 1800s, an era you can explore at the Railroad Depot.
This town has a soft spot for “man's best friend”, do not miss Dog Mountain, a 150-acre outdoor art gallery dedicated to the bond between dogs and their owners—because who does not like a bit of quirky charm? In the summer, the Kingdom Maple Festival brings together the region’s best food, music, and art, creating a local buzz that is hard to beat.
Woodstock
Woodstock is everything you could want from a New England town—historic, charming, and more picturesque than you can even imagine. One of its prime attractions, Billings Farm and Museum, is a working dairy farm that offers a glimpse into Vermont’s rural past with live farm demonstrations and tours. The Marsh-Billings-Rockefeller National Historical Park is the only national park in Vermont, offering trails and educational exhibits on conservation and the history of the Rockefeller family. Not to be outdone in architecture, the Woodstock Inn & Resort is a classic, established in 1793, where history meets luxury in a hotel that has hosted presidents and celebrities alike.
Woodstock is also famous for its covered bridges, the most notable being the Middle Bridge, which connects the village to the surrounding countryside. For a greater understanding of the town’s past, the Woodstock History Center uncovers everything from Native American history to the impact of the Industrial Revolution on the local economy. After taking in the past, The Prince & The Pauper Restaurant is right next door, so your afternoon plans practically arrange themselves.
Burlington
Burlington might be Vermont's largest city, but do not expect to find big city chaos here. With just over 40,000 residents, it is a perfect example of how small-town charm can coexist with a lively arts scene while having plenty of outdoor activities. One of Burlington's main attractions is the Church Street Marketplace, a bustling four-block stretch that feels like an outdoor art gallery with a side of artisanal coffee and even a Ben & Jerry’s ice cream parlor. For some history, the Ethan Allen Homestead Museum takes you back to the days of the Revolutionary War and the Green Mountain Boys, offering insight into one of Vermont’s most famous figures.
For nature lovers, Lakeside Park along Lake Champlain is a dream—where you can fish, boat, or simply sit back and watch the sunset over the water. On a similar note, the nearby Lake Champlain Maritime Museum brings Vermont’s maritime role in early American history to life, including its role in the War of 1812.
Brattleboro
Brattleboro is a town with a creative spirit, and that energy is apparent from the moment you arrive. The Brattleboro Museum and Art Center, the transformed town rail station established in 1972, showcases contemporary art, focusing on works that connect the community. If you are in the mood for an unconventional outing, The Retreat Tower offers a unique view of the town—once home to a mental hospital, now stands as a monument from the 19th century. At the heart of Brattleboro is the Brattleboro Common, a historic town square that’s hosted public events since the 1700s. Whether it's a lively farmers market in the summer or a cozy winter market, this open space brings the whole town together.
If you are in town on Friday, attend the weekly Gallery Walk, where you will be treated to local galleries, artisan booths, food trucks, and a general celebration of Brattleboro's vibrant creative community. Need to travel by rail? The Brattleboro Transportation Center links you to the Amtrak Vermonter service, putting Brattleboro on the map as a great point to explore the region.
Newport
Newport is a town tucked away on the shores of Lake Memphremagog, and though it might be small, it is bursting with things to do. This lake, which stretches into Canada, offers boating, fishing, and unparalleled lakefront views. The Memphremagog Historical Society Of Newport is a great option for anyone interested in learning of the town’s origins—from its early settler days to its development into a resort town. Alternatively, one can take a moment to relax in the iconic St. Mary Star of the Sea Catholic Church along Clermont Terrace.
While in town, if you need a place to get your heart rate up, the trails at Memphremagog Trails and Eagle Point Trail provide you sweeping views of both the lake and the surrounding Green Mountains. Lastly, The Waterfront Plaza is the spot for events, with local craft fairs, live concerts, and more.
Montpelier
Montpelier may hold the title as the smallest state capital in the U.S., with a population hovering around 8,000, but do not let its size fool you—it is brimming with things to explore. The Vermont State House, completed in 1859, is the heart of the city, showcasing Greek Revival architecture and its iconic gold dome, standing tall amidst the city’s tree-lined streets. The Vermont Historical Society Museum outlines some of the state’s key moments, including Vermont’s critical role in the abolitionist movement. Furthermore, one can take a step back into religious history at the Saint Augustine Church, a massive Gothic Revival structure in town.
After a morning of history, step into nature by taking a stroll through Hubbard Park, an excellent spot to enjoy an afternoon walk with the family dog, or find a tree to sit under and read a good book. This urban oasis features miles of hiking trails, with the Pavilion atop the hill providing fantastic city views. In the evenings, catch a performance at the Lost Nation Theater, known for its community-driven productions that showcase local talent year-round.
Castleton
The list of things to do in Castleton never seems to run out. The town is perched beside Lake Bomoseen, where opportunities for your family to enjoy boating, swimming, and fishing await in all seasons. For history buffs, Castleton University, founded in 1787, is one of the oldest public colleges in the state and remains a staple of local life. The Castleton Village Historic District, listed on the National Register of Historic Places, is a walk back in time, with its collection of 19th-century buildings still standing proud. On the other hand, those interested in a different type of culture can visit the Granger House or Fine Art Center in town. These galleries showcase various art styles, creating a unique environment full of creativity.
Stowe
As far as relaxing and enjoyable vacation destinations go, Stowe can go toe-to-toe with the best of them. The town was first chartered in 1763. However, most settlers did not arrive to establish the town until 1793. Known as a haven for those with a passion for the great outdoors, it first gained its reputation as a summer resort destination in the mid-1800s, so it has long since been a place where you can actually forget about your to-do list.
The historic district is packed with 19th-century architecture, like The Meeting House, built in 1818, is the town's oldest still active public building. Stowe is also home to the Trapp Family Lodge, founded by the von Trapps themselves in the summer of 1950 (yes, those von Trapps from The Sound of Music), so you can wander the hills that inspired the famous family’s musical escape. Furthermore, the town’s main street, lined with charming shops and local cafes like Woodland Baking & Coffee, practically dares you to take your time—and take it all in. Whether you are here to ski the slopes of Mount Mansfield, less than ten miles from town, or simply sip hot cocoa while watching the snow fall outside a cozy inn, Stowe is all about slow living.
Conclusion
Forget the hustle; these communities embrace the idea that life’s best moments are the ones that take a little longer. You could be savoring a locally made wool sweater, hiking up a mountain, or enjoying an impromptu chat with a farmer at the market; these towns give you room to breathe. It is all about slowing down, soaking in the quiet, and discovering the kinds of experiences that make you wonder why you did not slow down sooner. So, if you are in search of a getaway where you can actually “unplug,” Vermont’s small towns are your antidote to the fast-paced world.
