7 Most Charming Small Towns In Vermont

Few states seem to capture that small-town charm quite like Vermont. After all, in towns like Shelburne, you can tour a teddy bear factory that feels straight out of childhood, while in Ludlow, cozy ski resorts and maple syrup shops make even the coldest winter day feel a little warmer. And then there is Woodstock, where the countryside farms honestly look like they belong in a Hallmark movie. These three towns are just a small sampling! The seven towns ahead rank among the most charming places to visit in 2026.

Shelburne

Nothing is more charming than a fluffy teddy bear, and in Shelburne, the Vermont Teddy Bear Factory has plenty. This beloved stuffed animal factory hosts year-round tours, providing a sneak peek at the assembly line where the bears are born and the teddy bear hospital where injured bears receive care. After your visit to the teddy bear factory, you can head over to Shelburne Farms, a working farm, open mid-May through mid-October, where visitors can watch the cheesemaking process, visit with farm animals, see some raptors, or take a walk on one of the farm’s nature trails. Lastly, squeeze in some culture and history at the Shelburne Museum, which is the largest art and history museum in northern New England, spanning 45 acres and 39 buildings.

Manchester

Manchester is a culturally rich town, home to bookstores, art centers, and even the former estate of the Lincoln Family! Travelers wanting to visit this estate can do so at The Hildene, The Lincoln Family Home, a 412-acre property with a Georgian revival home, a 12-mile trail system, and gardens built by President Lincoln’s granddaughter, among other historic gems. The town is also home to the Southern Vermont Arts Center, a lovely center with a modern museum complex, a 400-seat theater, studio facilities, and the largest sculpture garden in the state. You won’t want to leave town without a souvenir! Make sure to stop by the Northshire Bookstore, a family-owned and independent business that has a large collection of new, used, and rare books to browse.

Wilmington

Wilmington sits right on the shores of the Harriman Reservoir, and while fewer than 400 people live there, the town is surprisingly lively. You can easily spend a morning or afternoon browsing the shops and restaurants downtown, popping into spots like 1836 Country Store, which sells maple syrup, fudge, cheddar cheese, candy, apple butters, jams, and much more. For lunch, you can dine at 19 South Main Restaurant, which serves home-cooked meals, brick oven pizza, seasonal cocktails, and craft beers. Leaving the downtown area, you can also spend some time exploring Molly Stark State Park, which has a hiking trail leading to a firetower, a picnic area, and a campground with plenty of tent and RV sites. You are also still in time for a ski trip this year! Mount Snow is just a 15-minute drive north and has 86 ski trails to enjoy.

Brattleboro

About half an hour east of Wilmington is Brattleboro, a charming town that lies on the banks of the Connecticut and West Rivers. For a waterfront meal, you can dine at The Marina, a seafood restaurant on the West River that serves clam chowder, mussels, salmon, fish and chips, and more. Once you are full from the meal, you can head over to the Brattleboro Museum & Art Center, which opened its doors in 1972, showcasing local and regional contemporary art and hosting up to 20 exhibitions annually. Your day can become even more memorable with a concert at the Stone Church, a renovated Victorian Gothic structure that now serves as a beloved music venue, hosting events throughout the year.

Ludlow

Ludlow is perhaps most famous for being home to the Okemo Mountain Resort, a renowned skiing resort that boasts the highest vertical drop in southern Vermont. With 667 skiable acres and 123 trails, you will quickly discover how much there is to explore here. If you are not a big skier, you may also enjoy golfing at the Fox Run Golf Club, a seasonal, 18-hole course set among rolling hills with varying elevation changes. Or maybe do some shopping at Green Mountain Sugar House, a local shop that has been specializing in Vermont maple products since 1955. High-quality maple syrup, pancake mix, maple cream, maple sugar, maple candy, and maple leaf cookies are a few of the products you can buy.

Woodstock

Woodstock is proud of its agricultural roots, and there is nothing the locals love more than sharing their family farms and fresh, seasonal food with anyone passing through. Billings Farm & Museum is the perfect example, a fully operating dairy farm with over 70 Jersey cows and a historic, 1890s farmhouse that visitors can explore. There is also a cheese shop where you can purchase the farm’s signature butter cheddar, Woodstock Reserve, and smoked cheddar cheeses! For more fresh food, stop by Ranch Camp for lunch, which serves burritos, tacos, burgers, wraps, salads, and other delicious dishes. There are also some great places to hike in the area, like Faulkner Park Trail, which features a trail gradually gaining in elevation with lots of switchbacks, leading to beautiful views of Woodstock from the top.

Stowe

Stowe is yet another iconic town for skiing in Vermont, offering the one and only Stowe Mountain Resort. This resort dates back nearly a century, to 1937, and is internationally renowned for its slopes. With a summit elevation of nearly 4,400 feet, 485 skiable acres, and 116 trails, skiers of all levels are practically guaranteed to have a memorable time here. After your ski day, you can have a cozy meal and drink at Idletyme Brewery & Restaurant, which serves both traditional brews and seasonal offerings, along with comfort food like mac n cheese, burgers, and pulled pork. The town’s lodges perfectly round out the weekend, with options like the Green Mountain Inn, which has over 100 comfy guest rooms to lodge in.

Vermont’s Countryside Charm

The Vermont countryside is a special place, with these seven towns showcasing the reason. Not only do they have some of the best ski resorts in New England, but they also have some of the most scenic river towns and state parks you could hope to visit. And then there are the many historic sites as well, such as the Lincoln Family Home and the Shelburne Museum! It looks like your 2026 is about to be the most charming one to date.