Hiking Near Brattleboro, VT

Southeastern Vermont, with ridgeline hardwood walks that melt out weeks before the high peaks. 36 mapped hiking routes sit within 25 miles, each with a real elevation profile computed from the trail geometry.

36Trails within 25 mi

19Rated easy

699 ftAverage gain

4.1 miClosest trailhead

Waterfall Hikes (13)Lake & Pond Hikes (26)Summit Hikes (331)Hikes to Shelters (35)Loop Hikes (88)Easy Hikes (186)Hardest Hikes (60)Long Day Hikes (67)Short Hikes (213)Fire Tower Hikes (13)

Closest trailheads to Brattleboro

Trail	From town	Distance	Gain	Difficulty
Pleasant Valley Reservoir via French Road	4.1 mi	1.9 mi	120 ft	Easy
Prospect Hill Trail	6.3 mi	1.1 mi	334 ft	Easy
Ridgeline Trail and West Cliff Trail Loop	10.3 mi	1.3 mi	172 ft	Easy
Putney Mountain via Ridgeline Trail	10.3 mi	1.2 mi	159 ft	Easy
Mount Olga via Bishop Trail	11.8 mi	1.5 mi	462 ft	Easy
Bishop Trail and Rim Run Loop	11.8 mi	1.9 mi	469 ft	Easy
Hogback Mountain via White's Loop	12 mi	2.2 mi	211 ft	Easy
Hogback Mountain via Douglas Trail	12.1 mi	2.4 mi	340 ft	Easy
Mount Olga via Tower Trail	12.1 mi	1.1 mi	253 ft	Easy
Putney Mountain via West Cliff Trail	12.6 mi	5.6 mi	1,435 ft	Hard

All 36 trails near Brattleboro

Ranked by popularity. Every figure is computed from the trail-snapped route geometry.

Trail	Area	Distance	Gain	Difficulty
Stratton Mountain via Appalachian Trail	Bromley & Stratton	6.7 mi	1,612 ft	Hard
Putney Mountain via West Cliff Trail	Brattleboro	5.6 mi	1,435 ft	Hard
Glastenbury Mountain via Appalachian Trail	Glastenbury	11.7 mi	1,857 ft	Strenuous
Bearclaw and Loop Trail	Brattleboro	1.9 mi	290 ft	Easy
Haystack Mountain Trail	Glastenbury	4 mi	1,008 ft	Moderate
Windmill Mountain via Holden Trail	Brattleboro	2.8 mi	461 ft	Moderate
Windmill Mountain via Jamie Latham Trail	Brattleboro	4.1 mi	428 ft	Moderate
Windmill Mountain via Radford-Smith Trail	Brattleboro	3.7 mi	983 ft	Moderate
Windmill Mountain via Cascade Trail	Brattleboro	2.7 mi	944 ft	Moderate
Windmill Mountain via Townline Trail	Brattleboro	3.8 mi	909 ft	Moderate
Hagar Hill via Appalachian Trail	Glastenbury	18.4 mi	1,575 ft	Strenuous
Hogback Mountain via White's Loop	Brattleboro	2.2 mi	211 ft	Easy
Hogback Mountain via Douglas Trail	Brattleboro	2.4 mi	340 ft	Easy
Hogback Mountain via Ware Road Connector	Brattleboro	3.9 mi	464 ft	Moderate
Hogback Mountain via Raponda Ridge Trail	Brattleboro	4.6 mi	545 ft	Moderate
Ridgeline Trail and West Cliff Trail Loop	Brattleboro	1.3 mi	172 ft	Easy
Bemis Hill Loop via Hemlock Trail	Brattleboro	3.2 mi	484 ft	Moderate
Putney Mountain via Ridgeline Trail	Brattleboro	1.2 mi	159 ft	Easy
Bemis Hill via Athens Access Path	Brattleboro	1.9 mi	657 ft	Easy
Stratton Mountain via Stratton Ridge Trail	Bromley & Stratton	1.2 mi	102 ft	Easy
Rice Hill via Loop Trail	Brattleboro	1.8 mi	258 ft	Easy
Mount Olga via Bishop Trail	Brattleboro	1.5 mi	462 ft	Easy
Mount Olga via Tower Trail	Brattleboro	1.1 mi	253 ft	Easy
Bemis Hill via Hemlock Trail	Brattleboro	3 mi	240 ft	Easy
Mount Olga Trail	Brattleboro	1.4 mi	525 ft	Easy
Prospect Hill Trail	Brattleboro	1.1 mi	334 ft	Easy
Lake Raponda via Whites Road to West Lake Road	Brattleboro	5.4 mi	593 ft	Moderate
Ledges overlook trail Loop	Brattleboro	1.4 mi	641 ft	Easy
Pleasant Valley Reservoir via French Road	Brattleboro	1.9 mi	120 ft	Easy
Ledges overlook trail	Brattleboro	1.6 mi	630 ft	Easy
Goddard Shelter via Appalachian Trail	Glastenbury	19.4 mi	2,088 ft	Strenuous
Bishop Trail and Rim Run Loop	Brattleboro	1.9 mi	469 ft	Easy
Hemlock Trail	Brattleboro	3.3 mi	897 ft	Moderate
Kid Gore Shelter via Appalachian Trail	Glastenbury	16.6 mi	1,992 ft	Strenuous
Ledges overlook trail (1.4 mi)	Brattleboro	1.4 mi	630 ft	Easy
Mount Olga Trail (1.5 mi)	Brattleboro	1.5 mi	389 ft	Easy

Frequently asked questions

Where can you hike near Brattleboro?

There are 36 mapped hiking routes within 25 miles of Brattleboro, 19 of them rated easy and 1 with 2,000 ft of climbing or more. The closest is Pleasant Valley Reservoir via French Road, about 4.1 miles out.

What is the best hike near Brattleboro?

Stratton Mountain via Appalachian Trail is the most popular: 6.7 miles with 1,612 ft of gain, rated hard, about 24.8 miles from town.

Are there easy hikes near Brattleboro?

Yes — 19 of the 36 routes within 25 miles are rated easy, averaging well under an hour of climbing.

Wider area

Peru, Bromley & Stratton32 trails Brattleboro & the Southeast29 trails Glastenbury & the Southern Greens13 trails

All Vermont hiking