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Routes
Road cycling routes
United States
Wisconsin
Milwaukee County
River Hills

Lakeshore State Park – Pebble Beach loop from Bayside

Routes
Road cycling routes
United States
Wisconsin
Milwaukee County
River Hills

Lakeshore State Park – Pebble Beach loop from Bayside

Hard

4.9

(4412)

15,331

riders

Lakeshore State Park – Pebble Beach loop from Bayside

05:03

114km

430m

Road cycling

Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride. The starting point of the route is right next to a parking lot.

Last updated: May 22, 2026

Tips

Includes a segment in which cycling is not permitted

After 18.2 km for 65 m

Waypoints

A

Start point

Parking

Get Directions

1

18.7 km

Milwaukee Art Museum

Highlight • Monument

Founded in 1988, the Milwaukee Art Museum houses almost 25,000 art works, as well as unique exhibitions and workshops. The building is spectacular; the Burke Brise Soleil 'wings' open with …

Tip by

2

19.6 km

Lakeshore State Park

Highlight • Lake

This 22-acre state park has a restored prairie and pebble beach. You can get views of the city of Milwaukee and views of Milwaukee Bay.

Tip by

3

20.2 km

Pebble Beach

Highlight • Beach

Pebble Beach within Lakeshore State Park is a small patch of beach along Lake Michigan. This particular section of beach is on a small inlet created by the patch of …

Tip by

4

27.8 km

View of Downtown Milwaukee from South Shore Drive

Highlight (Segment) • Viewpoint

Riding down South Shore Drive is a great way to take in the beautiful views of Downtown Milwaukee and the lake. There's a park and a number of restaurants and …

Tip by

5

31.4 km

Oak Leaf Trail — Shore line

Highlight (Segment) • Cycleway

A beautiful path with expansive views of Lake Michigan. A perfect path to cycle on, on a still summers day.

Tip by

6

39.5 km

Grant Park Beach

Highlight • Beach

Grant Park Drive runs along the coast but is separated from Grant Park Beach by a strip of woodland. There are some trails through the woods so you can access …

Tip by

7

45.8 km

Abandoned Ladish Sand Pit

Highlight • Structure

The Abandoned Ladish Sand Pit is often filled in with water and right off of the Oak Creek Trail. Oak Creek runs right behind it, making this spot a nice …

Tip by

8

65.6 km

Oak Leaf Trail

Highlight • Trail

A great little pond to make a rest stop along your bike ride on the Oak Leaf trail There are usually people fishing on the shore to take a look at.

Tip by

B

114 km

End point

Parking

Loading

Way Types & Surfaces

Way Types

52.9 km

40.8 km

12.2 km

7.88 km

167 m

< 100 m

< 100 m

Surfaces

82.2 km

30.9 km

723 m

232 m

< 100 m

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Elevation

Elevation

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

Highest point (240 m)

Lowest point (170 m)

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Weather

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Today

Tuesday 7 July

28°C

15°C

0 %

Additional weather tips

Max wind speed: 13.0 km/h

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Description

The Lakeshore State Park – Pebble Beach loop from Bayside is one of those road cycling routes that truly tests your endurance: a difficult 70.8-mile (113.9 km) journey with 1427 feet (435 metres) of climbing over roughly 5 hours and 2 minutes. This challenging ride is best suited for experienced road cyclists looking for a long day in the saddle, combining urban landscapes with serene waterfront views.

What to expect on Lakeshore State Park – Pebble Beach loop from Bayside

As you embark on this extensive loop from Bayside, you'll find yourself navigating a diverse landscape that transitions from suburban roads to the vibrant Milwaukee cityscape. The highlight is undoubtedly Lakeshore State Park itself, an urban oasis offering spectacular panoramic views of Lake Michigan and the city skyline. You'll cycle past iconic landmarks like the Milwaukee Art Museum, known for its striking architecture, before entering the park's restored prairie, alive with native grasses and wildflowers. The tranquil pebble beach within the park provides a peaceful respite. While the park's internal trails are generally flat and well-paved, the overall difficulty of this route comes from its considerable distance and cumulative elevation gain, making it a demanding ride for those seeking a significant challenge.

Planning your visit

Accessing Lakeshore State Park is straightforward, as no state park vehicle admission sticker is required. The park's paved trails seamlessly connect to the broader Oak Leaf Trail and the Hank Aaron State Trail, offering options for extending your ride if you're feeling ambitious. Spring and fall are particularly excellent times to visit, especially if you're interested in birdwatching, as the park lies on a major migratory flyway. Be prepared for a long day on the bike, ensuring you carry adequate hydration and nutrition for the full 5 hours and 2 minutes estimated duration.

Trail details

  • Distance: 70.8 miles (113.9 km)
  • Elevation gain: 1427 feet (435 metres)
  • Difficulty: difficult
  • Estimated time: 5 hours and 2 minutes

Nearby routes

Easy

3.0

47

Oak Leaf Trail: Milwaukee River and Lake Loop

01:44h

41.7km

140m

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