Shaftsbury’s streams are home to trout and offer some of the finest small stream fishing to be found in The Shires region. The small ponds by Airport Road and the old Whipple Mill are stocked each year and are ideal for youth to experience the excitement of their first catch. Hunters enjoy the seasonal taking of game such as white tail deer, turkey, bear, and moose… all in a tightly controlled way that is humane and vital to preserve the habitat that those populations rely upon. The Vermont Department of Fish and Wildlife provides detailed information on rules and regulations for enjoying hunting and fishing.

Outdoor enthusiasts will discover natures beauty in every corner of the town, including the Lake Shaftsbury State Park with it's trail system, swimming facilties, boat rentals, event pavilion, and other amenities. Shaftsbury is located near the heart of the Green Mountain National Forest, where there are literally hundreds of miles of wilderness and trails just to the east of town, including one of Vermont’s only "ghost" towns… the town of Glastenbury.

A favorite for hiking is the Robert Frost Trail. Located near the southern border with Bennington off Route 7A, the trail links the Robert Frost Stone House Museum with Lake Paran in North Bennington.