Exploring Vermont | Southern Vermont

From Rutland to Bennington to Brattleboro to White River Junction –– the four corners, so to speak –– Southern Vermont is dominated by mountains and rivers. Almost anywhere you turn there is a ski area: Killington, Pico, Ascutney, Stratton, Okemo, Bromley and Mt. Snow are the big ones.
Colleges like Castleton, Green Mountain, St. Joseph’s make the Rutland area youthful and vibrant. Brattleboro, Bennington, Manchester and Arlington were some of the first towns to be established in Vermont and help make Southern Vermont the state’s most historic region.
Anyway you slice it, Southern Vermont has a little bit of everything.
A town with plenty of food and shopping, with even more fun close by, Manchester doesn’t have a college but it has just about everything else.
If you’re spending a day here, you could break up your day of shopping at the numerous outlets by stopping for lunch at Zoey’s Deli. Big sandwiches, hot or cold, on homemade bread with fresh, homemade potato chips make Zoey’s hard to beat.
Within 25 minutes, you can go skiing and snowboarding in the winter (Bromley, Stratton), swimming in the summer (the marble quarry in Dorset, the Battenkill River in Arlington, Emerald Lake State Park in East Dorset), or take a tour of Hildene, the stunning home of Abraham Lincoln’s descendents, with its many rooms and manicured gardens.
Getting there: Manchester is located in Bennington County at the crossroads of Route 30 and Route 7, between Rutland and Bennington (about 20-40 minutes in each direction).
It’s awfully close to New Hampshire, but, luckily for Vermont, the biggest town in southeast Vermont is still on the good side of the Connecticut River.
For a bite to eat, try Amy’s Bakery (baked goods, etc…) or Top of the Hill Grill (great barbeque!). Walk off any extra calories with a stroll through downtown, which features many historic buildings still in use, or head to the woods and ponds around the Brattleboro Retreat.
Fun facts: Every year you can see cows taking over the town with the Strolling of the Heifers event, and, if you happen to forget your clothes, Brattleboro has made headlines for its policy on public nudity –– it became more strict last year, so watch out because it’s not allowed now in downtown or near schools and churches.
Getting there: Brattleboro is in the southeast corner of the state, in Windham County, with exits on Interstate 91. Routes 9 and 30 come to an end here.
Woodstock looks, feels and is, in fact, historic. And beautiful to boot.
Woodstock just looks and feels different than a lot of other Vermont towns. The houses seem to be a few feet too close to the street –– almost on the street, really –– and look like something out of the 1800s.
Woodstock, though, is not too old and stuffy for young people. You can go tubing or fishing in the Ottaquechee River, which runs through the town. Also nearby are the Billings Farm and Museum, a slice of history, straight out of 1890, the Quechee Gorge, and the Vermont Institute of Natural Science Nature Center.
Fun fact: The town green is designed to be the exact shape and size of the main deck of the infamous U.S. navy warship, U.S.S. Maine, which was sunk by the Spanish in 1898, sparking the Spanish-American War.
Getting there: Woodstock lies at the junction of Route 4, Route 12 and Route 106. It is about a 15 minute drive east on Route 4 to Interstate 89, or a 30 minute drive west to Rutland.