Bennington, New Hampshire offers a hands-on encounter with autumn’s vivid transformation and vibrant birdlife. Fall foliage here doesn’t just decorate the landscape; it challenges the hiker to move through a forest alive with rustling leaves that crunch underfoot, their fiery colors pushing forward like an eager audience urging you on. The trails wind through mixed hardwoods and gentle swells—terrain that invites both casual walkers and seasoned hikers to tune in to the natural rhythms of the season.

Start with the Lipsky Farm Trail, a moderate 3.5-mile loop with an elevation gain of around 700 feet. The forest canopy leans in close along shaded paths, letting shafts of autumn sunlight drip through, spotlighting maple and birch leaves burning in gold and red. Keep your eyes sharp for the ebony flash of a black-capped chickadee darting between branches—this trail gives a front-row seat to fall bird migrations, and its diverse habitat welcomes ruffed grouse and cedar waxwings.

For those eager to stay closer to water, the Dunbar Brook Trail introduces a gentler hike. In just under two miles with a modest 300-foot elevation increase, this path hugs the brook’s edge where the water dares you to follow its brisk current. The birdlife here includes belted kingfishers sending sharp calls and the occasional great blue heron standing stoic in the shallows. Alongside bright yellow viburnum and blazing sumac, this trail offers a quieter side of fall’s drama.

Plan your outings between mid-September and late October to catch the peak colors and peak birdwatching activity. Early starts reward you with calmer air and dew-touched leaves, while late afternoon brings a warmer glow perfect for photography. The ground can turn slippery from fallen leaves and early frost—choose footwear with good traction, and pack water; the crisp autumn air can still dry you out faster than it seems.

Bennington’s trails are fierce in their own way: the terrain demands respect but is never unforgiving. Shoulder your pack with enough layers to meet sudden temperature shifts and bring binoculars to truly engage with the resident and migratory birds. Whether you’re stepping lightly or pressing forward, these walks are a call to meet a landscape vividly alive and fiercely itself.