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Winchester

Winchester

Easy hikes and walks around Winchester

4.6

(94)

1,189

hikers

188

hikes

Exploring Winchester on foot is a delightful way to connect with nature. To help you make the most of your adventures, we’ve compiled the top easy hikes and walks around Winchester. Perfect for short hikes, kid-friendly excursions, and family-friendly outings, these routes offer something for everyone.

Last updated: November 8, 2025

hikers

1. Whipple Hill Conservation Land loop — Lexington, Massachusetts

3.54km

00:59

60m

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

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Easy

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2. Mystic Lakes Trail — Medford

4.54km

01:10

10m

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

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Easy

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3. Bear Hill Observatory loop — Middlesex Fells Reservation

4.42km

01:11

50m

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

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4. Horn Pond loop from Shakerhill

5.56km

01:27

30m

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

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Easy

5.0

(1)

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5. North Reservoir loop from Melrose

4.73km

01:14

30m

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

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Easy

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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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Easy hikes and walks around Winchester

1. Whipple Hill Conservation Land loop — Lexington, Massachusetts

2. Mystic Lakes Trail — Medford

3. Bear Hill Observatory loop — Middlesex Fells Reservation

4. Horn Pond loop from Shakerhill

5. North Reservoir loop from Melrose

Most popular routes around Winchester

Most popular attractions around Winchester

Get inspired with the komoot mobile app

Explore more

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