Sherman Hill – Quassy loop from Waterbury
Sherman Hill – Quassy loop from Waterbury
3.1
(2)
79
riders
Sherman Hill – Quassy loop from Waterbury
02:08
42.4km
560m
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: May 18, 2026
Waypoints
Start point
Bus stop
Get Directions
25.4 km
Sherman Hill
Highlight • Climb
Tip by
28.9 km
Quassy
Highlight • Structure
Tip by
32.9 km
Fenn Pond
Highlight • Lake
Tip by
33.4 km
Middlebury Greenway (Chase Road Section)
Highlight (Segment) • Cycleway
Tip by
42.4 km
End point
Bus stop
Way Types & Surfaces
Way Types
19.3 km
14.7 km
4.48 km
3.87 km
Surfaces
38.1 km
3.78 km
419 m
< 100 m
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Elevation
Highest point (240 m)
Lowest point (70 m)
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Weather
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Today
Sunday 12 July
30°C
16°C
0 %
Additional weather tips
Max wind speed: 6.0 km/h
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Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
Description
If you're looking for a road cycling route that truly tests your legs and offers a rewarding mix of terrain, the Sherman Hill – Quassy loop from Waterbury is a moderate 26.3-mile (42.4 km) ride with 1828 feet (557 metres) of climbing, typically taking around 2 hours and 8 minutes. This route is perfect for experienced cyclists seeking a challenge beyond flat stretches and a journey through varied landscapes.
What to expect on Sherman Hill – Quassy loop from Waterbury
Expect a ride of contrasts, from the paved roads with their significant elevation changes to the potentially rougher, unpaved sections within the Trolley Bed Preserve Trail, which follows South Brook past a small pond and dam. You'll pass by the Middlebury Greenway, leading towards Quassy Amusement Park and offering glimpses of Lake Quassapaug. Be prepared for steep inclines, including a long, steep hill climb on the return, making this route best suited for road cyclists with good fitness who enjoy varied terrain and a bit of a challenge.
Planning your visit
Parking is available, with the Old Sherman Hill Road parking lot mentioned as a return point. Given the varied terrain and potential for rougher sections, checking local conditions before you go is always a good idea. This route is best enjoyed when the weather is clear, allowing for optimal cycling conditions on both paved and unpaved segments.
Trail details
- Distance: 26.3 miles (42.4 km)
- Elevation gain: 1828 feet (557 metres)
- Difficulty: moderate
- Estimated time: 2 hours and 8 minutes
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