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Routes
Bike touring routes & trails
United States
Vermont
Windham County
Brattleboro

Cushman Park – Weatherhead Hollow Pond loop from Brattleboro

Routes
Bike touring routes & trails
United States
Vermont
Windham County
Brattleboro

Cushman Park – Weatherhead Hollow Pond loop from Brattleboro

Moderate

4.9

(6137)

8,008

riders

Cushman Park – Weatherhead Hollow Pond loop from Brattleboro

03:30

55.5km

440m

Cycling

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels. The starting point of the route is accessible with public transport.

Last updated: May 22, 2026

Waypoints

A

Start point

Train Station

Get Directions

1

22.4 km

Sawyer Pond

Highlight • Lake

Sawyer Pond lies on both sides of Old Vernon Road. This is a pretty spot to ride by because you are surrounded by water on both sides.

Tip by

2

29.7 km

Cushman Park

Highlight • Natural

Cushman Park, being right next to the Darwin Scott Wildlife Management Area, provides a green space for the public to enjoy. The park was donated back in 1908, and the …

Tip by

3

41.2 km

Weatherhead Hollow Pond

Highlight • Lake

A place of tranquility. Weatherhead Hollow pond is the ideal place to relax yourself and embrace some of nature's finest gifts: the soothing of the mind with smooth sound.
The …

Tip by

41.7 km

Weatherhead Hollow Pond

Lake

B

55.5 km

End point

Train Station

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Way Types & Surfaces

Way Types

36.8 km

16.2 km

2.46 km

< 100 m

Surfaces

50.6 km

4.80 km

< 100 m

< 100 m

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Elevation

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

Highest point (220 m)

Lowest point (60 m)

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Weather

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Friday 10 July

28°C

19°C

-- %

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Description

If you're looking for a touring cycling adventure that combines a solid workout with scenic Vermont charm, the Cushman Park – Weatherhead Hollow Pond loop from Brattleboro offers a moderate challenge. This route covers 34.5 miles (55.5 km) with 1427 feet (435 metres) of elevation gain, typically taking around 3 hours and 30 minutes to complete. It's a great option for cyclists who enjoy rolling terrain and are comfortable navigating less formally documented routes in the Brattleboro area.

What to expect on Cushman Park – Weatherhead Hollow Pond loop from Brattleboro

While specific details for this particular Cushman Park – Weatherhead Hollow Pond loop are not widely published, you can generally expect a classic Brattleboro touring cycling experience. The region is known for its picturesque routes through Vermont's rolling hills, often utilizing a mix of paved and well-maintained dirt roads. You'll encounter a balance of challenging climbs and rewarding descents, with views of the natural landscape. This route is best suited for confident touring cyclists who appreciate exploring local roads and perhaps discovering hidden gems, rather than following a strictly defined, formally marked trail.

Planning your visit

Given the limited public information on this specific loop, planning your visit will require a bit more local insight. For the best experience on Brattleboro cycling routes, it's highly advisable to consult local cycling maps, forums, or speak directly with local bike shops in Brattleboro. They can provide up-to-date information on road conditions, suitable sections for touring bikes, and any specific points of interest along the way. Parking in Brattleboro is available in various downtown locations, which could serve as a convenient starting point.

Trail details

  • Distance: 34.5 miles (55.5 km)
  • Elevation gain: 1427 feet (435 metres)
  • Difficulty: moderate
  • Estimated time: 3 hours and 30 minutes

Nearby routes

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Ashuelot Recreational Rail Trail

03:47h

42.0km

130m

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