The best road cycling routes around Wakefield
4.6
(24)
709
riders
14
rides
Last updated: October 22, 2025
5.0
(1)
26
riders
1. Lake Quannapowitt – Pond Pasture at Baldpate Pond loop from Greenwood
102km
04:09
560m
560m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(1)
14
riders
2. Field Pond – Harold Parker State Forest loop from Wakefield
39.5km
01:39
200m
200m
Intermediate road ride. Great for any fitness level. Some segments of this route may be unpaved and difficult to ride.
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12
riders
3. Middleton Pond loop from Wakefield
37.1km
01:52
200m
200m
Intermediate road ride. Great for any fitness level. Some segments of this route may be unpaved and difficult to ride.
5.0
(3)
11
riders
4. Roadbike loop from Greenwood
32.2km
01:17
130m
130m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
6
riders
5. Harold Parker State Forest – Lake Quannapowitt loop from Wakefield
61.3km
02:30
360m
360m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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