Brattleboro is a region in southeastern Vermont, characterized by its diverse landscape of rolling hills, dense forests, and the prominent Connecticut and West Rivers. This varied terrain provides a natural setting for a wide range of outdoor pursuits. The area's geography makes it suitable for several sports like hiking, jogging, road cycling, gravel biking, and more, offering varied experiences from riverside paths to challenging climbs.
Brattleboro offers a variety of outdoor activities and routes for…
47
Routes
5
(6)
Average rating
225
People visited

7
hikers
3.37km
01:03
120m
120m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

2
hikers
2.45km
00:46
90m
90m
Moderate hike. Great for any fitness level. Mostly accessible paths. Sure-footedness required.

2.93km
01:09
210m
20m
Moderate hike. Great for any fitness level. Mostly accessible paths. Sure-footedness required.

2.91km
00:45
20m
10m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
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3
runners
6.19km
01:04
290m
290m
Hard run. Good fitness required. Sure-footedness, sturdy shoes and alpine experience required.

1
runners
4.85km
00:32
50m
50m
Easy run. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

9.74km
01:00
30m
30m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

3.90km
00:26
80m
80m
Easy run. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
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15
riders
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

2
riders
30.8km
02:17
710m
710m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

4
riders
33.4km
02:00
490m
490m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

3
riders
23.1km
01:29
410m
410m
Moderate gravel ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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14
riders
63.1km
03:07
660m
660m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

8
riders
53.1km
02:17
460m
460m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

8
riders
94.3km
04:16
960m
960m
Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.

7
riders
55.6km
02:31
600m
600m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
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7
riders
24.9km
01:40
200m
200m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

4
riders
24.1km
01:39
310m
310m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

5
riders
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

4
riders
24.7km
02:03
340m
340m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Brattleboro offers a range of outdoor activities including hiking, jogging, road cycling, and gravel biking. The region features 21 routes with an average rating of 4.85 stars from 382 visitors on komoot. These activities utilize the diverse landscape of rolling hills, forests, and rivers.
Popular hiking options in Brattleboro include the Retreat Trails, a 10-mile (16 km) network of paths, and the West River Trail, which offers a 36-mile (58 km) scenic path along the West River. Fort Dummer State Park also provides several easy hiking paths. For more options, refer to the Hiking around Brattleboro guide.
Yes, Brattleboro offers several easy hiking options. Fort Dummer State Park has easy paths like the Sunset and Sunrise loop trails within its 217 acres. The lower section of the West River Trail is also accessible from Brattleboro and features a relatively flat, soft dirt surface suitable for easy walks. The Easy hikes around Brattleboro guide provides more details.
Many hiking trails in Brattleboro are suitable for jogging. The West River Trail is particularly noted for its relatively flat and soft dirt surface, which is easy on the knees. Other options include the Fort Hill Recreational Rail Trail and the Retreat Farm Trails. More routes are available in the Running Trails around Brattleboro guide.
Cyclists can explore miles of scenic byways and quiet country roads throughout Windham County. These routes often feature rolling hills and picturesque valleys with historic farmhouses. Komoot highlights several road cycling routes around Brattleboro, including loops around Sawyer Pond and Weatherhead Hollow Pond. Consult the Road Cycling Routes around Brattleboro guide for specific tours.
Brattleboro is a hub for gravel biking due to its abundance of well-maintained dirt roads. The 'Roundabout Brattleboro' is a notable 2-3 day bikepacking loop that features a mix of doubletrack, gravel, backroads, and some singletrack. The Gravel biking around Brattleboro guide offers additional routes.
Trails near Brattleboro offer various scenic views. Wantastiquet Mountain Natural Area, located across the Connecticut River, provides panoramic views of the Connecticut River Valley and Green Mountains. Putney Mountain also offers over 15 miles (24 km) of trails with views of surrounding ski areas.
Komoot offers several guides for Brattleboro, including Hiking around Brattleboro, Easy hikes around Brattleboro, Running Trails around Brattleboro, Road Cycling Routes around Brattleboro, Gravel biking around Brattleboro, and Cycling around Brattleboro.
Brattleboro is a popular destination on komoot, with 21 routes available across various sports. These routes have been explored by 382 visitors and hold an average rating of 4.85 out of 5 stars, indicating high satisfaction among users.
The Brattleboro region is defined by the Connecticut and West Rivers, which offer scenic views and recreational opportunities. The landscape also includes rolling hills, dense forests, and notable features like Round and Black mountains. Iconic covered bridges add to the picturesque charm.
Yes, several trails in Brattleboro are suitable for families. Fort Dummer State Park offers easy hiking paths, and the lower section of the West River Trail provides a relatively flat surface ideal for walking. The Bonnyvale Environmental Education Center (BEEC) also has 2 miles (3.2 km) of trails showcasing nature.
For official tourism information about Brattleboro, the Love Brattleboro VT website is a comprehensive portal. The Town of Brattleboro's official website is also available for general inquiries.
The Town of Brattleboro can be contacted by phone at +1-802-254-4541 for general inquiries. The Downtown Brattleboro Alliance can be reached at 802-257-4886 for information related to the downtown area.

