Middlebury is an beautiful college campus in an idyllic college town. There is wonderful running around the campus and in the surrounding area. The Trail Around Middlebury (TAM) is an 18-mile loop, which encircles the town and links hundreds of acres of land, schools, and other local landmarks.
The Jackson Trail is a great 4 mile segment (out and back) of the TAM for running, easily accessible from town. It starts in line with a normally cow-filled field and then follows a stream bank, complete with sights of a small gorge before opening up to a meadow.
Another beautiful route is the around the Middlebury College Trails. Start west of the Middlebury College baseball fields, on South Street. Follow signs for the TAM west as you boarder the perimeter of the Middlebury College Golf Course. The final section goes through a mix of open and wooded land, with wonderful Adirondack views from one rocky knoll. This section ends at the Jackson Trailhead on Rt. 23 in Weybridge for a total of 4.6 miles.Route Map