The best road cycling routes around Naugatuck
4.9
(31)
388
riders
53
rides
Last updated: October 16, 2025
5.0
(8)
103
riders
1. Granite Hill view loop from Prospect
50.5km
02:05
240m
240m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
15
riders
2. Judd Hill Pond – Cox Nature Reserve loop from Middlebury
47.6km
02:23
640m
640m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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5
riders
3. Judd Hill Pond – Sherman Hill loop from Southbury Historic District No. 1
53.3km
02:37
640m
640m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
2
riders
4. Sherman Hill – Fenn Pond loop from Hillside Historic District
42.0km
02:02
550m
550m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
3
riders
5. Long Meadow Pond – East Spring Brook loop from Middlebury
53.4km
02:38
670m
670m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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