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Bike touring routes & trails

Winthrop Harbor

Simmons Island Beach – Anna's on the Lake loop from Winthrop Harbor

Bike touring routes & trails

Winthrop Harbor

Simmons Island Beach – Anna's on the Lake loop from Winthrop Harbor

Moderate

2.8

(15)

35

riders

Simmons Island Beach – Anna's on the Lake loop from Winthrop Harbor

02:38

44.9km

100m

Cycling

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels. The starting point of the route is accessible with public transport.

Last updated: August 2, 2026

Tips

Cycling is not permitted along parts of this route

After 28.4 km for 54 m

After 29.6 km for 55 m

Waypoints

A

Start point

Train Station

1.14 km

Spring Bluff Forest Preserve

Nature Reserve

5.05 km

Chiwaukee Prairie State Natural Area

Nature Reserve

28.4 km

Bay

Bay

4

28.8 km

Simmons Island Beach

Highlight • Beach

A lovely beach and park on the shores of Lake Michigan. There's a paved bike trail along the waterfront. It's a big beach, so plenty of space to spread out your volleyball net and have a picnic.

Tip by

5

29.6 km

Anna's on the Lake

Highlight • Cafe

Awesome cafe and restaurant with great vibes and views over the lake. Quaint indoor seating and plenty of patio space as well. Vegetarian and vegan food options.

Tip by

B

44.9 km

End point

Train Station

Way Types & Surfaces

Way Types

21.9 km

19.4 km

2.87 km

375 m

235 m

130 m

Surfaces

34.4 km

9.34 km

947 m

222 m

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Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

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Weather

Powered by Foreca

Today

Friday 9 October

21°C

9°C

50 %

Additional weather tips

Max wind speed: 18.0 km/h

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