Hiking in Southern Vermont

Winding Trails, Quiet Woods, and Peak Experiences

Southern Vermont is a hiker’s paradise—home to winding forest paths, panoramic peaks, serene ponds, and one of the country’s most historic long-distance trails. Whether you're seeking a short nature walk, a moderate waterfall hike, or a full-day summit adventure, the towns of Manchester, Dorset, Winhall, Stratton, Arlington, Sunderland, Sandgate, Londonderry, Weston, Peru, Landgrove, Rupert, Pawlet, and Danby offer some of New England’s most rewarding trail experiences.

Hiking by Town

Community Trails, Wilderness Access, and Scenic Summits

Manchester, Vermont

• Equinox Preserve and Pond – Over 11 miles of well-maintained trails at the base of Mount Equinox, with options from gentle woodland walks to steeper, view-filled climbs.
• Mount Equinox via Red Gate Trail or Skyline Drive (foot access) – A challenging hike to the tallest peak in the Taconic Range, with spectacular summit views and a connection to the historic Skyline Drive.
  
• Lye Brook Falls Trail (GMNF) – A moderate 4.6-mile round trip hike through the Lye Brook Wilderness to one of Vermont’s tallest waterfalls.
  

Dorset, Vermont

• Owls Head Town Forest – A short but steep trail to a rocky outcrop with sweeping views of Dorset Valley. Perfect for sunsets and foliage.
  
• Dorset Quarry Trails – Informal forest trails surrounding the famous Dorset Marble Quarry; a great option for casual exploring.
  
• Cutler Memorial Forest – Quiet trails ideal for nature walks and peaceful forest time close to the village.

Winhall

• Winhall Forest Trails – Community-access forest paths with gentle grades, great for dog walking, family outings, and solo rambles.
  
• Grout Pond Recreation Area (GMNF) – An extensive loop trail around a pristine pond, great for hiking, snowshoeing, and camping. Connects to the Long Trail system via nearby side trails.
  

Stratton

• Stratton Mountain via Long Trail (GMNF) – A must-do regional hike to the historic Stratton fire tower, the birthplace of both the Long Trail and Appalachian Trail.
  
• Stratton Pond (GMNF) – A beautiful alpine pond accessed via the Stratton Pond Trail or Long Trail. Options for day hikes or backpacking.
  
• Stratton-Arlington Road Trailheads – Key access point for the Long Trail, Grout Pond, and wilderness hiking.
  

Arlington, Vermont

• Bald Mountain Trail – A rugged and rewarding hike with panoramic summit views, wildflowers, and frequent wildlife sightings.
  
• Roaring Branch / West Ridge Trail (GMNF) – Access to remote and wild areas of the Glastenbury Wilderness via Kelley Stand Road.
  

Sunderland, Vermont

• Lye Brook Falls Trail (GMNF) – Accessed from the Manchester side but located in Sunderland, this scenic trail through the Green Mountain National Forest leads to an impressive cascade.
  
• Branch Pond Trailhead (GMNF) – Connects with Stratton Pond and other remote wilderness routes. Perfect for longer loops and quiet backcountry access.
  

Sandgate, Vermont

• Class 4 Roads and Backcountry Walks – While lacking formal trails, Sandgate offers peaceful gravel roads, wooded lanes, and scenic “walk-in-the-woods” experiences perfect for solitude seekers.
  

Londonderry, Vermont

• Lowell Lake State Park – An easy 3.5-mile loop around a quiet lake with birdwatching, interpretive signage, and a historic cemetery. A local favorite for families and picnics.
  
• Magic Mountain (off-season) – In warmer months, hikers can ascend the ski trails for views of the valley and beyond.
  

Weston, Vermont

• Weston Town Forest – A lesser-known trail system near the village center, offering light hiking and local nature immersion.
  
• Nearby Access to Green Mountain Trails – While Weston itself has smaller trails, it’s within easy driving distance of Peru Peak Wilderness and White Rocks areas.
  

Peru, Vermont

• Hapgood Pond Recreation Area – Short, scenic trails around a forest pond with access to picnic areas, swimming, and the edge of GMNF hiking areas.
  
• Access to Stratton Pond and Long Trail (GMNF) – Peru lies within reach of several trailheads leading into major backcountry routes in the Green Mountains.
  

Landgrove, Vermont

• Landgrove Hollow Trails and Roads – Quiet backroads and wooded trails perfect for scenic, low-impact hiking and snowshoeing. A great area for fall foliage walks.
  

Rupert, Vermont

• Merck Forest and Farmland Center – Over 30 miles of hiking trails winding through working farmland, forests, and ridge views. Great for all-day hikes, family outings, and overnight stays in rustic cabins.
  

Pawlet, Vermont

• Haystack Mountain – A moderately steep 1.6-mile climb with one of the best open-summit views in Southern Vermont. Ideal for sunrise hikes or quick afternoon adventures.
  
• Bromley Brook & Flower Brook Paths – Informal and scenic walking options through the Pawlet countryside.
  

Danby, Vermont

• White Rocks National Recreation Area (GMNF) – Explore the Ice Beds Trail, White Rocks Cliff Trail, and scenic overlooks. Dramatic rock formations, high elevation, and geological features make this a standout.
  
• Peru Peak Wilderness Access (GMNF) – Includes portions of the Long Trail, rugged terrain, and quiet ridgelines for experienced hikers and backpackers.
  

Trails of the Green Mountain National Forest

Iconic Terrain, Peaceful Wilderness, and the Historic Long Trail

Many of the towns above provide direct access to the Green Mountain National Forest (GMNF)—a massive, federally protected wilderness that spans Southern Vermont—and to the legendary Long Trail, the oldest long-distance hiking trail in the U.S.

Highlights:

• Stratton Mountain – Climb to the summit fire tower via the Long Trail.
  
• Stratton Pond – Backpacker favorite with alpine scenery and quiet.
• Lye Brook Wilderness – Waterfalls, ridge trails, and solitude just outside Manchester.
  
• Grout Pond & Branch Pond – Excellent loops and winter-friendly routes.
• White Rocks National Recreation Area – Dramatic views and Ice Beds Trail near Danby.
  
• Peru Peak Wilderness – Rugged, remote, and rewarding for the seasoned hiker.
  
• Roaring Branch & West Ridge Trails – Remote Glastenbury Wilderness access via Arlington/Sunderland.

Take a Hike — Southern Vermont Style

With its mix of town trails, scenic lookouts, quiet backroads, and vast wilderness routes, Southern Vermont is a hiker’s dream. Whether you’re out for an hour or a weekend, there’s always something new to discover—one step at a time.