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Routes
Road cycling routes
United States
Wisconsin
Milwaukee County
Milwaukee

Oak Leaf Trail: Milwaukee River and Lake Loop

Easy

4.7

(4852)

16,640

riders

Oak Leaf Trail: Milwaukee River and Lake Loop

01:44

41.7km

140m

Road cycling

This easy 25.9-mile road cycling loop in Milwaukee offers scenic views of Lake Michigan and the Milwaukee River, passing iconic landmarks.

Last updated: February 26, 2026

Waypoints

A

Start point

Parking

Get Directions

1

2.24 km

Bradford Beach

Highlight • Beach

Bradford Beach is an open, sandy beach just off the side of the Oak Leaf Trail. You pass a number of beaches as you bike along the paved path, and Bradford Beach is the biggest with the most amenities. If you are wanting views of the bay and ferry, this is a great spot for that, too.

Tip by

2

29.4 km

Lincoln Park

Highlight • Rest Area

Lincoln Park has lovely river landscapes in abundance and sports fields. You can also play golf or visit the aquatic center in the park. Opening hours are 6am until 10pm.

Tip by

3

39.2 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 the museum and at noon.

You can visit from 10am until 5pm Wednesday to Sunday (and until 8pm on Thursdays).

Tip by

B

41.7 km

End point

Parking

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Way Types & Surfaces

Way Types

27.0 km

9.27 km

4.56 km

817 m

< 100 m

< 100 m

Surfaces

33.9 km

7.67 km

< 100 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.

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Weather

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Today

Wednesday 6 May

12°C

3°C

0 %

Additional weather tips

Max wind speed: 22.0 km/h

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This route was planned by komoot.

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Frequently Asked Questions

What is the overall difficulty of the Oak Leaf Trail: Milwaukee River and Lake Loop?

This loop is generally considered an easy road ride, suitable for most fitness levels. While there are a couple of short climbs on the southern half of the lakefront section, the majority of the route is accessible. However, be aware that some busier sections can be congested with other users like joggers and walkers.

What kind of terrain and surface can I expect on this route?

The majority of the route consists of smooth asphalt paving, making it ideal for road bikes. You'll primarily ride on dedicated cycleways, roads, and streets. There are only very small, negligible sections that might be unpaved.

What are some scenic highlights or landmarks along the way?

The loop offers stunning waterfront views of Lake Michigan and passes by popular spots like Bradford Beach. You'll also ride through historic Lake Park and Veterans Park, with sights of sailboats and classic Milwaukee architecture. Along the Milwaukee River, you'll enjoy lovely river landscapes, especially in parks like Lincoln Park. The route also provides direct access to the Milwaukee Art Museum.

Is the Oak Leaf Trail: Milwaukee River and Lake Loop dog-friendly?

The Oak Leaf Trail system, including this loop, is generally multi-use and popular with walkers and runners, many of whom bring dogs. It's best practice to keep your dog on a leash and ensure they are well-behaved around other trail users.

What is the best time of year to cycle this loop?

The trail is enjoyable throughout the warmer months. Spring and fall offer pleasant temperatures and beautiful scenery. Summer is also great, but be prepared for potentially more crowds, especially on lakefront sections. Winter cycling is possible but depends on snow and ice conditions.

Where can I park to access the trail, and is public transport available?

The Oak Leaf Trail system has numerous access points throughout Milwaukee County. For this specific loop, you can find parking near many of the parks it passes through, such as Lincoln Park or areas along the lakefront. Milwaukee's public transportation system also provides access to various points along the broader Oak Leaf Trail network.

Do I need any permits or pay entrance fees to use the trail?

No, there are no permits or entrance fees required to cycle the Oak Leaf Trail: Milwaukee River and Lake Loop. It is a public multi-use trail system.

Does this route connect with other trails in Milwaukee?

Yes, this loop is part of the extensive Oak Leaf Trail system. Specifically, it incorporates significant sections of the Oak Leaf Trail Milwaukee River Line, the Oak Leaf Trail Zip Line, and the Oak Leaf Trail Lake Loop. It also overlaps with parts of the Milwaukee Bicycle Route.

How long does it typically take to complete this road cycling loop?

On average, completing the 41.7 km (25.9 miles) loop by racebike takes approximately 1 hour and 44 minutes, depending on your pace and how often you stop to enjoy the sights.

Are there amenities like cafes or restaurants along the route?

Yes, as the trail passes through urban areas and popular parks, you'll find various amenities. There are cafes, restaurants, and pubs accessible near different sections of the loop, particularly in areas close to downtown Milwaukee and along the lakefront.

Is this trail suitable for families with children?

Given its easy difficulty and mostly paved surfaces, the loop can be suitable for families. However, be mindful that some sections, especially along the lakefront, can be busy with other users, which might require more caution with younger or less experienced riders.

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