Retreat Trails are an extensive network of two trail systems totaling over 11 miles adjacent to downtown, managed by the Windham Foundation. Many of these trails are over 100 years old, and mostly well-graded, offering pleasant walking and mountain biking. Highlights include the Retreat Tower and the Brattleboro Outing Club 90-meter ski jump.

Location: 4 trailheads with kiosks: 1) Route 30, north of downtown at the Retreat Farm and Grafton Village Cheese; 2) on Cedar Street, 0.2 mi. from Route 30 or 0.5 mi. from Western Avenue Route 9); 3) at Solar Hill, 289 Western Avenue (Route 9), 0.25 mi. east of Exit 2; and 4) on Upper Dummerston Road, 0.4 mi. from Route 30, just before the Interstate 91 underpass.