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United States

Connecticut

Lower Connecticut River Valley Planning Region

Deep River – Jennings Pond loop from Centerbrook

Routes

Bike touring routes & trails

United States

Connecticut

Lower Connecticut River Valley Planning Region

Deep River – Jennings Pond loop from Centerbrook

Moderate

4.7

(6122)

15,588

riders

Deep River – Jennings Pond loop from Centerbrook

02:00

33.4km

230m

Cycling

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels. The starting point of the route is right next to a parking lot.

Last updated: April 29, 2026

Tips

Temporary access restrictions

Includes segments with temporary access restrictions.

After 31.7 km for 110 m

Customers only

Waypoints

Start point

Parking

Get Directions

2.88 km

Deep River

Highlight • Settlement

This town embodies the quintessential charm of New England, with its picturesque Main Street lined with boutiques, cafes, and historic landmarks.

Tip by

5.80 km

Jennings Pond

Highlight • Lake

Jennings Pond is a pond created by a small dam on the eastern side of the pond which sits between two private properties. The pond is surrounded by trees and …

Tip by

8.78 km

Pattaconk Brook Waterfall

Highlight • Waterfall

There is a cute waterfall right next to the road where Pattaconk Brook flows through Town Park. You get a particularly good view if you are travelling south-east to north-west.

Tip by

9.88 km

Beautiful Cedar Lake is a local recreational area for the residents of Chester. Two springs feed into this 80-acre water body. Its tree-lined shore and tranquil setting make it a beautiful vista when cycling past on W. Main Street.

Tip by

22.5 km

Mount Tom

Highlight • Summit

This peak may be diminutive, but it's still a nice little stopover to enjoy some views. Look for some green open spaces to the southeast, and glimpses of much larger conservation areas to the east, southwest, and west.

Tip by

23.1 km

Town Open Space (West Pond Meadow Road)

Highlight • Forest

Surrounded by tall woodland, this town open space provides a great spot for you to jump off the bike and take a rest. Take care whilst pulling back onto the road.

Tip by

33.4 km

End point

Parking

Way Types & Surfaces

Way Types

25.5 km

7.74 km

190 m

< 100 m

Surfaces

28.7 km

4.19 km

555 m

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

Highest point (120 m)

Lowest point (0 m)

Weather

Today

Saturday 20 June

26°C

16°C

34 %

Additional weather tips

Max wind speed: 19.0 km/h

to get more detailed weather forecasts along your route

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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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Deep River – Jennings Pond loop from Centerbrook

Deep River

Jennings Pond

Pattaconk Brook Waterfall

Cedar Lake

Mount Tom

Town Open Space (West Pond Meadow Road)

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