Mile Around Woods

The Mile Around Woods Trail begins at the Park-McCullough House parking area on Park Street in North Bennington, Vermont, and makes a full circuit through scenic, conserved land managed by the Bennington Area Trail System and local land trusts. This route follows gently graded carriage roads and forest paths through open meadows, mixed hardwood forest, and quiet farm fields. From the trailhead, hikers can walk in either direction to complete the loop—both ways quickly lead to a broad, well-maintained path with minimal elevation change. Along the way, expect views of the Green Mountains in the distance, especially where the trail opens onto high meadows. Occasional benches offer places to pause and enjoy the landscape. The route passes through a mix of wooded and open terrain, making it especially enjoyable for families or anyone seeking a mellow outing in southern Vermont. This area is open year-round and is also popular for snowshoeing in winter. Leashed dogs are allowed, but fires and camping are not permitted. While this is a low-hazard area, ticks are common in warmer months, and some sections may be muddy during spring thaw. The route’s ease, scenic variety, and proximity to historic North Bennington make it one of the best easy hikes in the region.