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Winchester

Winchester

The best MTB trails around Winchester

4.5

(53)

610

riders

rides

Mountain biking around Winchester is a great to experience more of the landscape. But it’s often tough to know where to start. To help you find the best mtb routes around Winchester, here are the best rides!

Last updated: December 16, 2025

4.8

(6)

riders

1. Middlesex Fell Reservation — Reservoir Trail Loop

9.99km

00:52

80m

Easy mountain bike ride. Great for any fitness level. Suitable for all skill levels.

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Easy

4.7

(6)

riders

2. Green Blazed and Reservoir Trails loop — Middlesex Fells Reservation

10.3km

00:55

100m

Easy mountain bike ride. Great for any fitness level. Suitable for all skill levels.

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Easy

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riders

3. Whipple Hill – Short Technical Loop

3.92km

00:22

60m

Easy mountain bike ride. Great for any fitness level. Suitable for all skill levels.

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Easy

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4. North Reservoir Shore – Fire roads around Pasture hill loop from Winchester Center

28.4km

02:29

350m

Moderate mountain bike ride. Good fitness required. Advanced riding skills necessary.

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Moderate

5.0

(1)

riders

5. North Reservoir Shore – Fire roads around Pasture hill loop from Countryside

31.7km

02:25

360m

Moderate mountain bike ride. Good fitness required. Advanced riding skills necessary.

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Moderate

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Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

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The best MTB trails around Winchester

1. Middlesex Fell Reservation — Reservoir Trail Loop

2. Green Blazed and Reservoir Trails loop — Middlesex Fells Reservation

3. Whipple Hill – Short Technical Loop

4. North Reservoir Shore – Fire roads around Pasture hill loop from Winchester Center

5. North Reservoir Shore – Fire roads around Pasture hill loop from Countryside

Most popular routes around Winchester

Most popular attractions around Winchester

Get inspired with the komoot mobile app

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