10 Most Beautiful Small Towns In Vermont You Should Visit
As the days begin to get shorter, and the air once more becomes crisp, the state of Vermont enters into one of its most popular tourist seasons, autumn. However, no matter when visitors play a trip to Vermont, tourists here will be astounded by all the beautiful towns awash with natural and historical appeal. While there are many American towns for which the same could be said, Vermont has an incredible ability to intertwine its small town history with its natural beauty, making the towns in this state special. However, with so many options, it can become challenging to choose where to visit. But have no fear! We have compiled a list of our favorite beautiful Vermont small towns that a visit to will guarantee a tranquil immersion into Vermont’s stunning aesthetic.
Manchester
Nothing is more relaxing than experiencing a beautiful sunrise over the autumnal foliage-covered foothills of the Adirondack Mountains, particularly from the balcony of a luxury hotel. It is this type of view that a stay in Manchester, Vermont, offers, along with a more curated local beauty that includes the many historic buildings found throughout Manchester’s townsite. Some of the prettiest historic buildings in Manchester are the old Bennington County Courthouse and the restored Equinox Hotel, now known as the Equinox Resort & Spa, a lovely, if somewhat pricey, place to stay. Other great accommodation options include the Kimpton Taconic Hotel, The Inn at Manchester, and Ormsby Hill.
Approximately 10 miles north of Manchester, you will find Emerald Lake State Park. If you are a hiker, this park is definitely for you. It has miles of trails around its namesake central feature, Emerald Lake, which is particularly pretty during the fall season. A must-see site in this region is the Georgian Revival home of Hildene Mansion, the estate owned and lived at by Robert Lincoln, the son of Abraham Lincoln. This property offers hiking and biking trails, with the historical mansion open to the public for tours.
Middlebury
With beautifully preserved and restored heritage sites, the village of Middlebury, Vermont, founded in 1761, is a highlight of central Vermont. Spend part of your visit exploring the gorgeous regional historic buildings, such as the Emma Willard House and the Thaddeus Chapman House, both along Vermont Route 30, and the Henry Sheldon Museum of Vermont History at number 1 Park Street. If you are looking to slow down for a day but still want to explore the beauty that surrounds Middlebury, booking a Vermont Wine Tasting Tour out of Middlebury will allow you both to taste local wine and witness Vermont in all its glory. Popular local wineries on many tasting tours include Lincoln Peak Vineyard and Winery, Neshobe River Winery, and Charlotte Village Winery.
Westminster
Not to be confused with the City of Westminster borough in London, England, the town of Westminster, Vermont, which owes its name to British society, is the oldest in the state, and as such, the local history spans back centuries. Much of historic Westminster has been preserved, including the Bradley Law Office along US Route 5, which dates back to 1810. The Westminster Terrace Historic District is also a great place to take in the historic visual delights of Westminster, with many landmark buildings standing in the shadows of the same trees planted as saplings when these buildings were built. One cannot help but marvel at this profound example of the cohesion of natural and human-made beauty. After exploring historic Westminster, spend some time hiking in the many local forests and parks, including Westminster Town Forest, Fanny Mason Forest, and Bellows Falls Village Forest, each offering a range of hikes and viewpoints.
Bennington
Looking for a town that combines American history and modern elegance? If so, Bennington, Vermont, is for you. Best known as the site of the Bennington Battle of 1777 during the Saratoga Campaign of the Revolutionary War, today, the soldiers lost in this battle are commemorated at the Bennington Battle Memorial, where a 93-meter obelisk has stood for nearly a century, the tallest man-built structure in all of Vermont.
While Bennington has a historic downtown area, some of the oldest and most visually appealing buildings fall beyond the town line. These include the Colonel Nathaniel Brush Home, built in 1775, the Walloomsac Inn, built in 1771, and the Jedidiah Dewey House, built in 1763, each stunning in their own right. For those interested in literature, the Robert Frost Stone House Museum is also in Bennington and open to visitors. Just south of Bennington, you will find the One World Conservation Center, a 96 acre property devoted to preserving and highlighting the magnificence of this region's natural meadowlands and wetlands.
Waitsfield
Welcome to Waitsfield, home to Vermont's best hiking, hunting, and fishing. Outside of Waitsfield, you will find some superb local hiking trails, such as those in the Roxbury State Forest, as well as the Warren Falls Trail and Moretown Falls Trail, each popular amongst locals and visitors alike, and which take hikers up close to experience the beauty of these two sets of waterfalls. If you have a way to get out of town a little farther, paying a visit to Camel's Hump State Park and Mount Mansfield State Forest will not be a regret, with these parks’s trails being particularly spectacular after the leaves change in the fall.
Despite all the local natural beauty in and around Waitsfield, the Waitsfield Village Historic District is this town’s true star. It includes buildings like the General Wait House, the oldest frame house in Waitsfield, first built in 1793. During peak tourist season, there are in-person walking tours of this district during which you can revel in the historic and natural ambiance of Waitsfield.
Warren
The small Vermont community of Warren has an approximate population of just under 2,000 residents. It is surrounded by mountains and sits in the Mad River Valley. For a gorgeous aerial view of Warren, take one of the various routes to the top of Mount Ellen, of which Jerusalem Trail, Long Trail from Lincoln Gap, and Long Trail from the Appalachian Gap are options. From the highest point of these trails, you will have an unparalleled view of the surrounding landscape, mountains, and Warren itself. This view is breathtaking in the fall season, making the trek up well worth it. Other great hikes in this beautiful region include Sunset Ledge Trail and Blueberry Lake Trail, with Warren Falls Trail taking hikers to the spectacular Warren Falls themselves.
Grafton
Ranked amongst the friendliest towns in Vermont, the village of Grafton, Vermont, is renowned for its abundance of well-preserved historical buildings. With a large historic district, Grafton marries nature and human infrastructure to perfection, each complimenting the other. Some of the oldest buildings in Grafton include the Enos Lovell House, dating to 1795, the Butterfield House (turned library), dating to the early 1800s, the Congregational Church, dating to 1834, and the Grafton Inn, which used to be a rural stagecoach hotel, and dates to 1801. Outside of town, there are a multitude of picturesque hiking options, some of the most popular trails including the Athens Dome Trail and the many trails that depart from Grafton’s Outdoor Center. After a long day of hiking, you will want to return to a relaxing environment, with Inn Victoria and Rowell’s Inn, located just outside of town, and the historic Grafton Inn, in the center of town, being lovely options.
Burlington
Once the mayoral district of current Vermont Senator Bernie Sanders, Sanders was the mayor of Burlington for eight years. In Burlington’s charming historic downtown, there are some fabulous markets, including the Church Street Marketplace, which has street performers, artisan crafts, and a range of events, including the New Year’s First Night Celebration and the Burlington Discover Jazz Festival. It is these festivals and community events that have created, in Burlington, an aesthetic beyond the physical that creates a beautiful atmosphere in Burlington. Around this community, you will find picturesque natural landscapes, with the Shelburne Pond Natural Area, Charlotte Park and Wildlife Refuge, and Charlotte Town Beach being some of the loveliest green spaces in and around town. If you are a history lover, a visit to Ethan Allen Tower and Ethan Allen Homestead Museum and Historic Site will enthrall you, visually and intellectually.
Waterbury
Home to the Waterbury Village Historic District, Waterbury, Vermont, is a history lover’s paradise. Visitors will want to visit some of the stunning local historic buildings, including the United Church of Christ, built in 1824, the Dr. Henry Janes House, home to Civil War surgeon Dr. Henry Janes, and now a public library per Dr. Janes’s will. Get to know the regional beauty around Waterbury by exploring the stunning green spaces, inside and outside of Waterbury, such as Little River State Park, CC Putnam State Forest, and Camel's Hump Forest Reserve. Cap your visit by staying at a converted historical building, such as the Old Stagecoach Inn, or slow down at one of the Bed and Breakfasts just outside of town, where you can enjoy the natural beauty of Vermont any time of year.
Brattleboro
Named for Major-General William Brattle, who never visited his namesake town once, Brattleboro, Vermont, is one of the oldest towns in the state. Brattleboro was one of Vermont's first non-indigenous permanent communities, founded in 1753. In its early years, this town was populated by mills and factory facilities, and collectively, it was not a visually appealing community. However, in the past half-century, Brattleboro has transformed into a visually appealing town in which historical buildings have been restored and repurposed, while there has also been a range of natural species re-introduced to this local.
Brattleboro is home to the largest organ factory in the United States, run by the Vermont Estey Company. It is no surprise then that Brattleboro has an Estey Organ Museum. This museum displays America’s gorgeous organ history, a visual timeline with samples of beautifully restored instruments going back to the beginning. If you are looking for some outdoor family fun in a scenic and pretty local, visit Pliny Park or Brattleboro Common. If you want a more strenuous activity, the trails at Wantastiquet Mountain Natural Area, notably the Wantastiquet Mountain Summit Trail, are popular and offer stunning views.
The Take Home
Vermont is filled with immense natural beauty that fills this entire state and surrounds most small towns in Vermont. From historic city centers, beautiful green spaces, and luxury accommodations, each of these discussed towns, and many others, guarantees a memorable visit to Vermont. No matter which small town you choose to visit, you need not sacrifice history for nature or vice versa, there are more than enough towns to enjoy where these things go hand in hand and produce a unique beauty all of Vermont’s own.
