Vermont's Beautiful Byway Is A Perfect Road Trip For Hikers Seeking Classic New England Charm And Views

If you're looking for the perfect Vermont road trip, look no further than the Molly Stark Byway. Named for the wife of the "Hero of Bennington," Revolutionary-era General John Stark, this route crosses the southern part of Vermont from east to west, although you can start on any end you like. Take the VT-9, and you'll discover trailheads leading to wonderful Green Mountain views and little hamlets with tales of historic figures, from military heroes such as Ethan Allen to poets like Robert Frost, as in the "I took the road less traveled by" Robert Frost.

The full route is 48 miles long, starting from the west side of the historic and walkable town of Bennington, and finishing in the quaint and artsy town of Brattleboro, or vice versa. You could finish the drive in an hour easily, but that would defeat the purpose of enjoying all the fantastic stopping points along the way. Here are the best places to eat and things to do along the Molly Stark Byway.

No matter which city you start and end in, you will want to take the time to explore Brattleboro and Bennington equally. Brattleboro has great stores downtown for vintage shopping, including Boomerang and Twice Upon a Time, and you can also check out the local art galleries. In Bennington, must-see landmarks are the famously photogenic covered bridges, such as the Paper Mill Village Bridge and Burt Henry Covered Bridge.

Going from east to west, key stops along the way include the Hogback Mountain Scenic Overlook, the "100-Mile View" that looks out over three states, and the Vermont Museum of Natural History in Marlboro, which has live animal exhibits with owls and bald eagles. After this, you'll pass through Molly Stark State Park, the byway's namesake, where the most popular trail is the 1.7-mile Mt. Olga Trail that leads to a fire tower with panoramic views. 

In the next town of Wilmington, a popular ski town near one of the best East Coast ski resorts, Mount Snow, you can find a hotel for the night or continue onward to the 306-foot-tall Bennington Battle Monument, which commemorates the 1777 defeat of British troops on this site during the Revolutionary War. This is the end of the byway, but you can extend your trip past Bennington by heading north to Shaftsbury and stopping at a major highlight for poetry fans, the Robert Frost Stone House Museum.

If you like to eat, Vermont is a great place to be. Farm-to-table restaurants are plentiful here, as are comfort food favorites like pancakes drenched in real maple syrup and microbreweries pumping out funky and innovative craft beers and ciders, such as the Madison Brewing Company in Bennington. In Brattleboro, go for lunch or dinner at Plated, which sets the scene for Vermont's robust and locally-minded culinary landscape with offerings that include espresso-rubbed pork chops and a charcuterie slate with local cheese. In Wilmington, you can stop at Dot's for coffee and a classic diner experience. If Bennington is your final destination, make reservations in advance at The Grille at Mount Anthony Country Club, which is open to the public for lunch and dinner.

If you've got a sweet tooth, it's also worth stopping at the Maple Museum in Marlboro, where you can learn how syrup is tapped and processed and pick up a souvenir to take home. This is also a great spot to buy artisan cheeses such as cheddar, which Vermont is famous for.