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Road cycling routes

South Central Connecticut Planning Region

Sherman Hill – Quassy loop from Waterbury

Road cycling routes

South Central Connecticut Planning Region

Sherman Hill – Quassy loop from Waterbury

Moderate

3.1

(2)

79

riders

Sherman Hill – Quassy loop from Waterbury

02:08

42.4km

520m

Road cycling

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride. The starting point of the route is accessible with public transport.

Last updated: August 19, 2026

Waypoints

A

Start point

Train Station

1

25.4 km

Sherman Hill

Highlight • Climb

Sherman Hill is a 604-foot hill on Old Sherman Hill Road in Woodbury. This is a nice little climb in a quiet residential area surrounded by forest and old stone walls.

Tip by

2

28.9 km

Quassy

Highlight • Structure

A one-stop shop for thrills, spills, and summer fun, offering classic amusement park rides, a water park called Splash Away Bay, and even access to Lake Quassapaug for swimming and relaxation.

Tip by

3

32.9 km

Fenn Pond

Highlight • Lake

Fenn Pond is a small freshwater pond between Middlebury Avenue and Charcoal Road. This attractive body of water is in an open field and surrounded by reeds, making it a peaceful spot to ride past.

Tip by

4

33.5 km

Middlebury Greenway (Chase Road Section)

Highlight (Segment) • Cycleway

This section of the Middlebury Greenway near Chase Road is an especially scenic bit of riding on this popular, paved multi-use path. You ride on the raised trail above a …

Tip by

B

42.4 km

End point

Train Station

Way Types & Surfaces

Way Types

18.8 km

13.5 km

6.61 km

3.38 km

117 m

< 100 m

Surfaces

38.5 km

3.42 km

455 m

< 100 m

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Elevation

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

Highest point (240 m)

Lowest point (70 m)

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Weather

Powered by Foreca

Today

Thursday 22 October

16°C

5°C

0 %

Additional weather tips

Max wind speed: 20.0 km/h

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