To help you find the best hikes and walks around Bridgeport, we’ve reviewed our full collection of trails and routes in the region. Browse all of the details of each route below — and explore more of the nature around Bridgeport.

Last updated: October 2, 2025

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1. Pequonnock Mountain Trail – Pequonnock River Valley Park

8.85km

02:20

80m

Intermediate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

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Intermediate

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2. Long Beach & Pleasure Beach loop — Bridgeport

5.73km

01:26

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. Mondo Ponds Nature Preserve loop — Milford

1.50km

00:23

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

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Easy

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4. Lake Mohegan Recreation Area – Lake Mohegan loop from Bridgeport Downtown North Historic District

4.54km

01:11

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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5. Lake Mohegan – Lake Mohegan Recreation Area loop from Bridgeport Downtown North Historic District

2.79km

00:44

20m

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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The best walks and hikes around Bridgeport

1. Pequonnock Mountain Trail – Pequonnock River Valley Park

2. Long Beach & Pleasure Beach loop — Bridgeport

3. Mondo Ponds Nature Preserve loop — Milford

4. Lake Mohegan Recreation Area – Lake Mohegan loop from Bridgeport Downtown North Historic District

5. Lake Mohegan – Lake Mohegan Recreation Area loop from Bridgeport Downtown North Historic District

Most popular routes around Bridgeport

Most popular attractions around Bridgeport

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