Unique Things to Do in Southern Vermont

Vermont marches to the beat of its own drum. We are proudly small town and welcoming here, historic and progressive, and we’re not afraid to do our own thing. Vermont is nothing if not unique, so why not take in the most unique, Vermonty things you can when you visit?

Many visitors get to Vermont from the south coming up I-91, and Brattleboro is the first exit, making it the perfect place to base yourself for a Vermont adventure. Voted “one of the best small towns in America” and named the 2023 Strong Town winner, Brattleboro is an art and nature haven that has always attracted people looking for something a little different.

Stay at a Landmark

There’s no better place to stay when visiting Vermont than a Landmark Trust USA property. Our 5 (soon to be 6 in Fall 2025!) properties are all whole house overnight vacation rentals in historic buildings than have been restored to highlight their unique historic character. Sleeping 2-8 people, with no taxes or fees and rates that meet or beat the chains, you won’t find a more charming and private escape. Plus, since we’re a nonprofit organization with a mission to preserve and restore historic properties, every penny from your stay goes right back into keeping these historic treasures alive and continuing to provide special immersive experiences with history.

Four of our properties are just outside of Brattleboro in the charming village of Dummerston:

• Naulakha, our flagship property, Rudyard Kipling’s 1892 home where he wrote The Jungle Book and other stories that led to his Nobel Prize in Literature, sleeps 8.

• Kipling’s Carriage House, an 1895 smaller version of Naulakha with a huge light-filled kitchen and sweeping views, sleeps 4.

• The Sugarhouse, a 1915 former maple sugarhouse nestled in the surrounding sugarbush, sleeps 2, dog friendly. It doesn’t get any more Vermont than this!

• Dutton Farmhouse, an 1849 Greek Revival farmhouse overlooking the Scott Farm orchard and the mountains of New Hampshire, sleeps 8.

• Coming Soon! Naulakha Stable, the loft in Naulakha’s 1896 Stable, formerly home to horses Nip & Tuck, is being rehabilitated into a cozy new rental option opening Fall 2025, sleeps 2.

And just about 45 scenic minutes west in the beautiful Deerfield Valley, is another overnight stay option for those who want a true escape:

• Amos Brown House, a truly peaceful 1802 brick farmhouse nestled on 30 private acres just steps from the MA border, sleeps 6, dog friendly.

Brattleboro and Beyond

There’s no shortage of activities in bustling Brattleboro. With over 13,000 people, this is a big city by Vermont standards, but it is small enough to feel eminently accessible and welcoming. One of the best ways to get to know the local community is by attending a First Friday Gallery Walk, when streets close, music fills the air, artists take to the streets, and hundreds gather to celebrate creativity and community.

Heirloom Apples

What’s more unique than a Cox’s Orange Pippin apple? Maybe an Esopus Spitzenburg or a Hubbarston Nonesuch? They’re fun to say and delicious to eat, and they’re just a few of the 130+ varieties of heirloom apples being kept alive by our Scott Farm Orchard. In active cultivation since 1791, Scott Farm (just steps from our Dummerston properties) is home to 23 historic structures and 30 acres of hillside orchards. Our apples are available each fall in our Farm Market, through mail order, and at local co-ops throughout New England and serve as the basis for our signature line of unique hard, sweet, and bubbly ciders. We also offer a seasonal outdoor café, pick-your-own orchards, and a fruit CSA in addition to serving as a venue for Vermont farm weddings, business functions, and celebrations of all kinds. A number of community events from Crêpe Nights to our annual Heirloom Apple Day bring people together at the farm to enjoy the harvest, the views, and one another.

Arts Mecca

The arts are at the heart of Brattleboro. Unique workshop spaces abound, from HatchSpace for woodworking to the New England Center for Circus Arts. Galleries are everywhere, and even the historic train station is now the exemplary Brattleboro Museum & Art Center. Not one but two historic church buildings are now devoted to the arts - Epsilon Spires, with its wide array of unique events, and The Stone Church, bringing in musical acts from across the spectrum. And the Latchis Theatre is a stunning “Grecco Deco” 1920s movie theater that will knock your socks off. Beyond Brattleboro, don’t miss the masterful puppetry work at Sandglass Theater or diverse programming of Next Stage Arts in Putney.

Foodie Fun

Vermont is known for beer, but the farm-to-table food, cider, and vegetarian fare are to die for as well. Pippin’s Café at Scott Farm offer sweeping views of the Vermont countryside, perfect baguette sandwiches, and flights of hard cider made on site from the farm’s own apples. One of the most unique spots in town is T.J. Buckley’s, a world-class restaurant with just a few seats in a restored 1925 Worcester dining car. For traditional diner food and ice cream, head to the scrumptious Royal Diner. A local favorite, Yalla offers the best Middle Eastern vegetarian food money can buy. Vegan A.F. also offers delicious eating in a refined environment. If you want to keep the literary vibe going from your stay at Naulakha, don’t miss the classic Kipling’s Tavern, a storied gem in operation since 1926.

The Deerfield Valley and Western Mass

This is nature’s wonderland, all easily accessible from your home base at our dog-friendly Amos Brown House in Whitingham, VT. Laid-back, outdoorsy, and close by you’ll find quaint small towns, welcoming people, and abundant recreational opportunities everywhere you look.

Southern Vermont’s Deerfield Valley

Billed as the place where Vermonting begins, the Deerfield Valley is centered on the bucolic small town charm of Wilmington and the ski haven of Mount Snow. Don’t miss the 100-mile view from Hogback Mountain or the many opportunities to enjoy the great outdoors at the Harriman Reservoir, which Forbes called Southern Vermont’s hidden gem. For breakfast or lunch, you’ll want to grab a seat at Dot’s in Wilmington for nostalgic comfort food. If you time your visit in the summer, the dulcet chamber music at the Marlboro Music Festival, housed at a gorgeous former college campus in the mountains, will add a touch of class.

Western Massachusetts

The charms, culture, and outdoor recreation of Western Massachusetts make this undiscovered corner of New England ripe for exploration. In Franklin County, you’ll find the exquisite Bridge of Flowers (as lovely as it sounds), world class rafting and ziplining at Zoar Outdoor, and the friendliest brewery in the state at The People’s Pint. The Berkshires region, just to the west, has been a cultural hub for generations. There you’ll find the largest contemporary art museum in North America - MASS MoCA. Hiking, biking, bird watching, cross-country skiing, snowshoeing, and snowmobiling are everywhere you look.

Want more?

New England is famous for recycling town names from state to state, but there is only one Brattleboro in the world, and we embrace it! For more on the arts capital of Vermont, check out the Downtown Brattleboro Alliance and Brattleboro Area Chamber of Commerce. And don’t sleep on the natural wonders of the Deerfield Valley next door. The Southern Vermont Deerfield Valley Chamber has everything you need to know.

Vermont is a vacation wonderland for a reason, and quirky and unique is the name of the game here. There are so much more to do in the Green Mountain State, and you can find it all at VermontVacation.com.

And of course we’ll forgive you if your hop over the border into New Hampshire or Massachusetts. They’re just minutes away after all! Franklin County and The Berkshires in MA and NH’s Monadnock Region are right next door and waiting to be explored too.

Wherever you visit, our Landmark Trust USA properties are the most unique places you can stay in Southern Vermont. Our history is waiting to welcome you!