Hiking in Brattleboro & the Southeast

Southeastern Vermont trades alpine terrain for ridgeline hardwood walks: Putney Mountain, Wantastiquet, and the Windmill Hill ridge are short, scenic, and hikeable weeks earlier in spring than the high Greens.

29Mapped trails

74 miTotal distance

515 ftAverage gain

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)

All 29 trails in Brattleboro & the Southeast

Sorted by popularity. Every distance and elevation figure below is computed from the trail-snapped route geometry, not estimated from a map.

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

Frequently asked questions

How many hiking trails are there in Brattleboro & the Southeast?

RidgeSync maps 29 hiking routes in Brattleboro & the Southeast, totalling about 74 miles with an average of 515 ft of elevation gain per hike.

What is the hardest hike in Brattleboro & the Southeast?

Putney Mountain via West Cliff Trail climbs the most, at 1,435 ft of gain over 5.6 miles.

What is the longest hike in Brattleboro & the Southeast?

Putney Mountain via West Cliff Trail is the longest mapped route at 5.6 miles.

When is the best time to hike in Brattleboro & the Southeast?

Late June through mid-October is the reliable window, and late September through mid-October is usually the best of it. Green Mountain Club and Vermont Forests, Parks & Recreation ask hikers to stay off trails above 2,500 ft during mud season, roughly mid-April through Memorial Day.

Nearby hiking areas

Glastenbury & the Southern Greens13 trails Peru, Bromley & Stratton32 trails Bennington & the Southwest Corner11 trails Manchester & the Taconic Range28 trails

All Vermont hiking areas