New Canaan – Siscowit Reservoir loop from Ridgefield

Western Connecticut Planning Region

Ridgefield

New Canaan – Siscowit Reservoir loop from Ridgefield

Moderate

4.8

(4738)

6,390

riders

New Canaan – Siscowit Reservoir loop from Ridgefield

02:31

53.8km

480m

Road cycling

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride. The starting point of the route is right next to a parking lot.

Last updated: September 26, 2026

Waypoints

Start point

Parking

Get Directions

971 m

Branchville Road Open Space

Highlight • Natural

This is the only protected open space right off Branchville Road, which makes it a great stopover if you're cycling this scenic route.

Tip by

5.99 km

Deer Run Pond

Highlight • Lake

Want a break from a scenic ride along Nod Road or nearby Whipstick Road? Pull off onto Nod West Drive for a few moments beside this small pond.

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6.94 km

Whipstick Road Open Space

Nature Reserve

8.96 km

Millstone Road Open Space

Nature Reserve

17.1 km

Cheese Spring Pond

Highlight (Segment) • Lake

This is a lovely road section on the way up to Pine Hill. All along this wetland, the trees, streams and ponds freshen the air to make your ride absolutely …

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22.4 km

Mill Pond Park

Highlight • Lake

Mill Pond Park is located off Millport Avenue and contains a large pond. There are some lovely walking trails nearby and if the weather is right you can ice skate …

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32.0 km

New Canaan

Highlight • Settlement

New Canaan is a wealthy little town about an hour's train ride away from Manhattan.

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37.1 km

West Road Pond

Highlight • Lake

39.6 km

Siscowit Reservoir

Highlight • Lake

The first dam across Rippowam River is thought to have been built here sometime in the 1700s by John Raymond. Throughout the years it has been rebuilt about as often …

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47.3 km

Onatru Reservation and Onatru Park

Highlight • Trail

Lewisboro Parks & Recreation are owned by the Town of Lewisboro. It encompasses the house, buildings, fields and a preserve that were donated to the local community in order to …

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53.8 km

End point

Parking

Way Types & Surfaces

Way Types

29.5 km

20.1 km

4.29 km

Surfaces

40.3 km

13.4 km