When it comes to things to do in Southern Vermont, the opportunities and experiences are endless. Whether it’s a Hogback Mountain hike, Southern Vermont skiing, checking out Brattleboro attractions, experiencing one of our many Vermont fall festivals or local breweries, or Lake Whitingham boating with the kids, there are activities for every kind of traveler in every season. Here are just a few.
Downtown Wilmington, Vt.
Historic district with charming local shops, art galleries, cafés, and restaurants
Home to artisan crafts, antiques, and handmade Vermont goods with shops including: Bartleby’s Books, Incurable Romantic, Pickwell’s Barn, 1836 Country Store, Hogback Mountain Country Store, Hayseed Gifts, River Valley Market, Quaigh Designs, The Village Roost, Matterhorn Apothecary, The Fashion Plate, Vermont Bowl Company, Jasper Decor & more.
Restaurants in Wilmington, Vt.
- Maple Leaf Tavern
- La Casita
- Village Roost (breakfast & lunch only)
- Valley Craft Ales
- 19 South Main
- Anchor Seafood Restaurant
- Alpenglow Bistro
- Dot’s (breakfast & lunch only)
- Folly
- Clara’s Cucina Italiana (in The White House)
- Wilmington Village Pub
- Wahoo’s Eatery
- North Star Pizza
- Cup n Saucer
Skiing, Snowboarding & Snowshoeing
Winter in Southern Vermont: Stay at The Crafts Inn and enjoy ski slopes, cross-country trails, and cozy winter vibes near Mount Snow and Wilmington’s festive village.
- Ski or snowboard the slopes of Mount Snow (10 minutes away) or Stratton Mountain (45 minutes away)
- Explore cross-country trails at nearby Prospect Mountain
- Strap on your snowshoes and trek some of the many trails in Wilmington, nearby Dover and beyond
Hiking
Within a half hour of Wilmington, Vermont, hikers will find an incredible variety of trails that showcase the natural beauty of Southern Vermont. From panoramic fire tower climbs like Mount Olga to peaceful woodland walks in Molly Stark and Woodford State Parks, the region offers trails for every ability and interest. Nearby Haystack Mountain provides a rewarding summit hike just minutes from downtown, while Hogback Mountain’s 100-Mile View offers breathtaking vistas with minimal effort.
Breweries, Wineries & Distilleries
Southern Vermont is home to a growing craft beverage scene, offering a unique blend of local breweries, distilleries, and wineries nestled among the region’s scenic mountains and small towns. You’ll find everything from small-batch spirits and award-winning IPAs to hand-crafted ciders and estate-grown wines.
- Beer Naked Brewery – Marlboro
- Snow Republic – Dover
Veteran-owned brew pub with food, wine, cocktails, live music, and positive vibes. - Vermont Distillers – Marlboro
Producers of the Metcalfe’s family of Liqueurs, Maple Bourbon, Honey Bourbon & Catamount Vodka as well as other limited edition spirits & liqueurs. - Putney Mountain Winery & Spirits – Putney
Swimming, Kayaking & Paddleboarding
Harriman Reservoir (Lake Whitingham)
- Vermont’s largest lake entirely within the state.
- Boating, kayaking, swimming, and picnicking
- Known for its calm waters and beautiful mountain views