The best road cycling routes around Wolfeboro
5.0
(1)
82
riders
21
rides
Last updated: November 11, 2025
21
riders
1. Lake Winnipesaukee loop — Wolfeboro
108km
05:01
1,180m
1,180m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
2
riders
2. Lake Wentworth loop — Wolfeboro
60.8km
02:37
530m
540m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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11
riders
3. Wolfeboro Town Forest – Goodwins Basin loop from Wolfeboro
36.9km
01:36
330m
330m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(1)
6
riders
4. Back Bay – Lake Wentworth loop from Wolfeboro
50.1km
02:16
480m
480m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
5
riders
5. Wolfeboro Town Forest loop from Wolfeboro
23.1km
01:13
340m
340m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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