Routes

Planner

Features

Updates

App

Get the App

Western Connecticut Planning Region

Western Connecticut Planning Region

The best running trails in Western Connecticut Planning Region

4.6

(15)

1,519

runners

271

runs

Running in Western Connecticut Planning Region is one of the best ways to explore more of this region. To help you discover the most beautiful places to run, we’ve reviewed our full collection of routes in Western Connecticut Planning Region—and are proud to present the best running trails. Click on any of the routes for more details and browse real tips and photos uploaded by other runners.

Last updated: October 25, 2025

runners

1. Old Mine Park loop via Pequonnock Valley Greenway — Trumbull, Connecticut

12.9km

01:22

120m

Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Navigate

Send to Phone

Save

Intermediate

runners

2. Bridgeport Seaside Beach Path — Seaside Park

5.61km

00:35

Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Navigate

Send to Phone

Save

Intermediate

Let us show you the way with the komoot mobile app

With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures in England and beyond.

runners

3. Twin Brooks Park loop via Pequonnock River Trail — Bridgeport, Connecticut

13.3km

01:24

70m

Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Navigate

Send to Phone

Save

Intermediate

runners

4. Indian Ledge Park loop — Trumbull, Connecticut

8.53km

01:03

90m

Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Navigate

Send to Phone

Save

Intermediate

runners

5. Sherwood Island Trail loop — Sherwood Island State Park

4.77km

00:30

10m

Easy run. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Navigate

Send to Phone

Save

Easy

5.0

(1)

runners

6. Saugatuck, Bedford, & Troop Trail loop — Devil's Den Nature Preserve

11.6km

01:26

120m

Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Navigate

Send to Phone

Save

Intermediate

runners

7. Stepney & Newtown Rail Trail — Trumbull, Connecticut

23.3km

02:32

130m

Expert run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Navigate

Send to Phone

Save

Expert

runners

8. Saugatuck Trail from Davis Hill Road — Easton, Connecticut

20.0km

02:29

260m

Expert run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Navigate

Send to Phone

Save

Expert

runners

9. Saugatuck Trail from Black Rock Turnpike — Easton, Connecticut

17.9km

02:13

250m

Expert run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Navigate

Send to Phone

Save

Expert

runners

10. Long Beach Trail & Pleasure Beach Park loop — Stratford, Connecticut

5.72km

00:39

10m

Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Navigate

Send to Phone

Save

Intermediate

Get access to more routes and recommendations from other explorers.

Already have an account?

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

Other adventures in Western Connecticut Planning Region

East Coast Greenway — An unforgettable ride along the Atlantic Seaboard

Cycling Collection by

Sue

The Appalachian Trail — America’s most iconic long-distance hike

Hiking Collection by

Jamie S.

Most popular routes in Western Connecticut Planning Region

Hiking in Western Connecticut Planning Region

Easy hikes in Western Connecticut Planning Region

Cycling in Western Connecticut Planning Region

Road Cycling Routes in Western Connecticut Planning Region

MTB Trails in Western Connecticut Planning Region

Waterfall hikes in Western Connecticut Planning Region

Gravel biking in Western Connecticut Planning Region

Most popular attractions in Western Connecticut Planning Region

Places to see

Lakes

Get inspired with the komoot mobile app

With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures around London and beyond.

Join komoot Now

Didn’t find what you were looking for?

Check out more Running Trails & Routes throughout Western Connecticut Planning Region below and find the perfect route in your destination.

Branchville Norwalk Lordship Noroton Heights Newtown Bethel Greenwich Sandy Hook Birchbank Mountain Open Space Taylor Corners Murray Shelton Bridgeport Indian Field Lakes West Putnam Memorial State Park Wilton Center Poplar Plains Knollcrest Kellogg Point Sherman Long Hill Greens Farms Old Greenwich Oronoque Stratford Downtown Paugussett State Forest Pootatuck State Forest Wooster Mountain State Park Stewart B. Mckinney National Wildlife Refuge Sheffield Island Unit Trout Brook Valley State Park Reserve Collis P. Huntington State Park Seth Low Pierrepont State Park Reserve Plattsville Candlewood Knolls Sail Harbor Route 7 Gateway Squantz Pond State Park Stamford Rocky Glen State Park Scenic Reserve Cos Cob Botsford Brookfield Center Ridgefield Georgetown Danbury Noroton Riverside Topstone Westport Village Candlewood Lake Club Stepney Ball Pond Darien Downtown South Wilton Lakeside Woods Redding Center Fairfield University Old Hill West Mountain New Canaan Candlewood Shores Cannondale Compo Candlewood Orchards East Village Dodgingtown Hawleyville Inglenook Mamanasco Lake Mianus River State Park Scenic Reserve Mill Plain Tokeneke Bigelow Corners Trumbull Center Tashua Rock Ridge Ridgebury Indian Well State Park Coleytown Glenville Lakes East Staples Southport Bogus Hill Daniels Farm Weston Saugatuck Pemberwick Byram Candlewood Isle Devils Den

Explore more

Browse the best Running Trails & Routes in other regions.

Capitol Planning Region South Central Connecticut Planning Region Lower Connecticut River Valley Planning Region Northeastern Connecticut Planning Region Southeastern Connecticut Planning Region Tolland County Northwest Hills Planning Region

The best running trails in Western Connecticut Planning Region

1. Old Mine Park loop via Pequonnock Valley Greenway — Trumbull, Connecticut

2. Bridgeport Seaside Beach Path — Seaside Park

3. Twin Brooks Park loop via Pequonnock River Trail — Bridgeport, Connecticut

4. Indian Ledge Park loop — Trumbull, Connecticut

5. Sherwood Island Trail loop — Sherwood Island State Park

6. Saugatuck, Bedford, & Troop Trail loop — Devil's Den Nature Preserve

7. Stepney & Newtown Rail Trail — Trumbull, Connecticut

8. Saugatuck Trail from Davis Hill Road — Easton, Connecticut

9. Saugatuck Trail from Black Rock Turnpike — Easton, Connecticut

10. Long Beach Trail & Pleasure Beach Park loop — Stratford, Connecticut

Other adventures in Western Connecticut Planning Region

Most popular routes in Western Connecticut Planning Region

Most popular attractions in Western Connecticut Planning Region

Get inspired with the komoot mobile app

Didn’t find what you were looking for?

Explore more

Get ready to conquer new peaks

We value your privacy ⛰️

We value your privacy ⛰️