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Western Connecticut Planning Region

Sail Harbor

Western Connecticut Planning Region

Sail Harbor

Easy hikes and walks around Sail Harbor

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Exploring Sail Harbor 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 Sail Harbor. Perfect for short hikes, kid-friendly excursions, and family-friendly outings, these routes offer something for everyone.

Last updated: November 16, 2025

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1. Still River Greenway — Brookfield, Connecticut

5.31km

01:21

20m

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

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2. Squantz Pond State Park loop — New Fairfield, Connecticut

3.76km

01:02

60m

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

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3. Williams Park loop — Brookfield, Connecticut

4.20km

01:08

60m

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

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4. Bear Mountain Reservation loop from Boulder Ridge

4.09km

01:09

80m

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

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5. Cranberry Mountain loop from Patterson

6.14km

01:42

110m

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

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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 Sail Harbor

1. Still River Greenway — Brookfield, Connecticut

2. Squantz Pond State Park loop — New Fairfield, Connecticut

3. Williams Park loop — Brookfield, Connecticut

4. Bear Mountain Reservation loop from Boulder Ridge

5. Cranberry Mountain loop from Patterson

Most popular routes around Sail Harbor

Most popular attractions around Sail Harbor

Get inspired with the komoot mobile app

Explore more

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