City Escape: Brattleboro, Vermont

City Escape: Brattleboro, Vermont

The word “pastoral” is overused when describing Vermont, but that might be because it fits the place to a tee. This north-to-south loop takes you through everything this beautiful state has to offer. You’ll pass gently flowing rivers, dense forests, small towns, and open fields with old stone fences before finishing it all with a climb up Hogback Mountain.

The scenery on this route is stunning, with each season adding its own flair to the mix. The entire route is paved, so you can ride this relaxing loop with whatever’s in your garage. I recommend reserving the whole day for this tour, as you’ll find many natural and historical sights that are absolutely worth a stop.


Approximately 174 miles

Lunch Stop

Mamma Tamara and Famiglia serves authentic, rustic southern Italian cuisine. This family-owned restaurant’s menu features to-die-for pasta, pizza, and sandwiches—just like Mama used to make. Find it at 137 North Main St, Wallingford, VT, (802) 446-6060.

Points of Interest

Hamilton Falls

Hamilton Falls, near Jamaica, VT, consists of a series of waterfalls, cascading through pines and hemlock into a series of large pools. This popular swimming hole is a great way to refresh on a hot summer day, but be careful as the rocks are steep and slippery.

Vermont Country Store

The Vermont Country Store is a huge establishment that has been in business since 1946. Tourists from far and wide flock here to browse clothes, hardware, food, furniture, and more in a historical setting. Find it at 657 Main St, Weston, VT.

Hildene, the Lincoln Family Home

The Hildene was the summer home of President Lincoln’s son, Robert Todd Lincoln, and his descendants from 1905 to 1975. Today, the Georgian Revival-style house is a gorgeous museum containing priceless furniture and objects belonging to the Lincoln family. Find it at 1005 Hildene Rd, Manchester, VT.

Robert Frost Stone House

World-renowned poet Robert Frost bought this 1769-built house for himself and his family, but fate tragically didn’t have a happy life in store for them. While living here, Frost wrote many of his famous poems, including “Stopping by Woods on a Snowy Evening.” Find it at 121 SR 7A, Shaftsbury, VT.