The best road cycling routes around Winnetka
4.8
(133)
2,020
riders
81
rides
Last updated: November 11, 2025
5.0
(21)
142
riders
1. Skokie Lagoon No. 3 – Skokie Lagoons loop from Indian Hill
37.8km
01:31
70m
60m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
3.5
(2)
224
riders
2. Lakefront Trail, Chicago – Lincoln Park loop from Kenilworth
52.0km
02:06
100m
100m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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5.0
(20)
196
riders
3. Skokie Lagoons – Skokie Lagoon No. 3 loop from Hubbard Woods
38.4km
01:30
60m
60m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
5.0
(27)
71
riders
4. Christ Church Churchyard – Gillson Park loop from Hubbard Woods
23.4km
01:23
60m
60m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
13
riders
5. Skokie Lagoon No. 3 loop from Hubbard Woods
7.80km
00:18
10m
10m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
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