Things to Do in Southwestern Vermont
Southwestern Vermont is known for its rich history, vibrant arts and culture scene, and breathtaking mountain views. With endless opportunities for relaxation and adventure, there’s no shortage of ways to spend your days amidst this pastoral landscape. Whether you’re dreaming of a peaceful escape, a couple’s retreat, or a last-minute getaway, this beautiful region is the ideal destination for any occasion. So, what are you waiting for? Read on to learn about the best things to do in The Shires of Vermont. Then, start planning your getaway!
Adventures in Arlington
Nestled between the Taconic Range and the Green Mountains, Arlington, VT, is an outdoor enthusiast’s dream. The Battenkill River flows through the heart of the historic village, making it the perfect place to explore and reconnect with nature. From hiking and kayaking to skiing and snowshoeing, this quintessential Vermont village offers something to visitors in every season!
Snowmobiling: Vermont Mountain Adventures www.vermontmountainadventures
Downhill Skiing / Snowboarding: Bromley Mountain, www.bromley.com – Opening November 28, 2025
Cross Country Skiing: Wild Wings Ski Touring Center, Peru www.wildwingsski.com
Cross Country Hildene Touring Ctr, Manchester, www.hildene.org
Killington Mountain www.killington.com – Open
- Summer
- White Water Rafting Discover the excitement of rafting on the West River, a true gem of Vermont. This journey offers breathtaking scenery and an exciting ride that will leave you with lasting memories.
- Enjoy panoramic views of Equinox Mountain
- Dorset Playhouse, Box Office:802.867.5777
- Weston Playhouse 703 Main St, Weston · (802) 824-8167
- Old Castle Theater 331 Main Street, Bennington – (802) 447-0564
- Embark on an outdoor adventure on the Battenkill River
- Go fly fishing for Native Brown trout
- Indulge in Vermont maple syrup at The Sugar Shack & visit the Norman Rockwell Exhibit
- Hike in the Green Mountain National Forest on part of the Appalachian Trail or Long Trail
- Enjoy the great outdoors at Green Mountain National Forest
- Taste your way through the Vermont Cheese Trail
- Satisfy your sweet tooth at the Village Peddler Chocolatorium
- Tour The Shires of Vermont’s Historic Covered Bridges
- Enjoy fresh produce, live music, at the seasonal Arlington Village Farmers Market
- Stay in a romantic room at the Arlington Inn & Spa
- Spoil yourself with one of our “In House” Massages
Must See Manchester
Just 15 minutes away from Arlington, Manchester is another quaint New England town full of history, art, and culture. Beautiful marble sidewalks line the downtown, white church steeples dot the skyline, and awe-inspiring art galleries fill the streets. Admire the lovely natural landscape in one of the two shire towns in Bennington County, Vermont.
Must See Manchester
Just 15 minutes away from Arlington, Manchester is another quaint New England town full of history, art, and culture. Beautiful marble sidewalks line the downtown, white church steeples dot the skyline, and awe-inspiring art galleries fill the streets. Admire the lovely natural landscape in one of the two shire towns in Bennington County, Vermont.
Our Favorite Manchester Attractions
- Hear beautiful music at The Manchester Music Festival
- Visit Hildene, the historic Lincoln Family Home
- Shop at the Manchester Designer Outlets
- Take a trip to the Southern Vermont Arts Center
- Shop for fresh produce at Manchester Farmers Market
- Sample artisan cheese at North Meadow Farm
- Explore the American Museum of Fly Fishing
- Lost Marble Brewery
Beautiful Bennington
Twenty minutes outside of Arlington is Bennington, VT. This is the second shire town in the county and used to be a mill town. History buffs and nature lovers alike will find something to love in Bennington. Here, you’ll also see many of Vermont’s most famous historic sites, farms, breweries, and farmers’ markets. There is also a beautiful, traditional downtown area with many shops, restaurants, and a popular brewery. How would you prefer to spend a day in this Southwestern Vermont village?
Spend a Day in This Southwestern Vermont Village
- Tour Bennington Museum
- Explore The Robert Frost Stone House Museum, the famous poet’s former home
- Visit The Park-McCullough House, an authentic Victorian mansion
- See a performance at Oldcastle Theatre
- Pick berries and shop for local products at The Apple Barn
- See the historic Bennington Battle Monument
- Spoil yourself with one of our “In House” Massages
- Enjoy a Southwestern Vermont craft beer at a Northshire Brewery