Bennington offers an outdoor recreation program that sponsors a variety of off-campus outdoor activities. Fall term excursions include a range of activities from canoeing and hiking to caving and rock climbing; spring activities include cross-country skiing, white-water rafting, and overnight snowshoeing trips.

Students can walk or bike the campus Blue Trail, an easy hike winding through the wooded parts of campus and connecting to several trails throughout the region, including the Mile-Around Woods. The trailhead is located at the north end of campus, behind the Davis Alumni House. Access to the Long Trail, Vermont's oldest long-distance hiking trail, is a short drive from campus.

Through the Bennington bike-share program, Bennington College community members can borrow one of ten hybrid bikes, helmet, and lock at no cost through the Crossett Library.

In warmer weather, students can visit the nearby Walloomsac and Battenkill Rivers or Lake Paran for fishing, canoeing or tubing, and swimming. Bennington and its surroundings are also home to numerous natural watering holes, water tubs, and water slides.

In the winter months, Bennington College is only a short drive to some of the best skiing and riding in the Northeast, as well as some of the region's best snowshoeing and cross-country skiing trails. The Crossett Library carries an expansive collection of area guidebooks for these and many other outdoor activities.