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 …

Last updated: September 12, 2025

4.8

(5)

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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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. Fire roads around Pasture hill loop from Medford

15.4km

01:18

120m

Intermediate mountain bike ride. Great for any fitness level. Advanced riding skills necessary.

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Intermediate

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

28.0km

02:27

360m

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

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Intermediate

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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. Fire roads around Pasture hill loop from Medford

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

Most popular routes around Winchester

Most popular attractions around Winchester

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