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Routes
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United States
Wisconsin
Milwaukee County

Shorewood

The best cycling routes around Shorewood

4.9

(27)

617

riders

41

rides

Touring cycling around Shorewood, Wisconsin, features routes along the scenic Lake Michigan shoreline and the Milwaukee River. The region is characterized by bluffs, ravines, and woodlands, offering diverse natural settings for cyclists. An extensive network of bike trails, including the Oak Leaf Trail, connects various parks and natural features. The terrain generally includes gentle gradients along the lake and river, with some varied elevation through wooded areas.

Best touring cycling routes around Shorewood

  • The most popular touring cycling route is Oak Leaf Trail: Southern Loop, a 51.8 miles (83.3 km) trail that takes 4 hours 45 minutes to complete. This moderate route explores a significant portion of the comprehensive Oak Leaf Trail system.
  • Another top favourite among local touring cyclists is Lakeshore State Park – Bradford Beach loop from Whitefish Bay, an easy 16.7 miles (26.9 km) path. This route offers views of Lake Michigan and passes through urban parkland.
  • Local touring cyclists also love the Milwaukee Pierhead Lighthouse – Bradford Beach loop from University of Wisconsin-Milwaukee, a 19.5 miles (31.4 km) trail leading through urban landscapes and along the lakefront, often completed in about 1 hour 50 minutes.
  • Touring cycling around Shorewood is defined by Lake Michigan shoreline paths, Milwaukee River banks, and extensive urban parkland. The network offers options for different ability levels, from easy loops to longer, moderate routes.
  • The routes in Shorewood are highly rated by the komoot community with an average score of 4.9 stars from over 20 reviews. More than 500 touring cyclists have used komoot to explore Shorewood's varied terrain.

Last updated: May 21, 2026

5.0

(2)

23

riders

#1.

Oak Leaf Trail: Southern Loop

83.3km

04:46

250m

250m

Cycle the moderate 51.8-mile (83.3 km) Oak Leaf Trail Southern Loop for scenic Lake Michigan views and paved paths in Milwaukee County.

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Moderate

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Easy
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Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Easy

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Easy
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Popular around Shorewood

Hiking around Shorewood

Road Cycling Routes around Shorewood

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Tips from the Community

Grant Gehweiler
July 17, 2025, Shorewood Railroad Pedestrian Bridge

Adjacent to the bridge is a historical marker that commemorates the commuter line and the old 400 passenger train that formerly to crossed a bridge here.

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Billed as "the most accessible beach in America" and as one of the cleanest beaches in the country, this spot can get pretty busy. It's free for day use and has a couple of on-site spots for food and refreshments.

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View of the Milwaukee river as it crosses under the Hoan Bridge at a very active boat landing.

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Nice view of downtown and South Shore Marina. Beer Garden and playground nearby.

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Sue
January 25, 2025, Milwaukee Art Museum

Situated on the city's beautiful waterfront, The Milwaukee Art Museum is the largest in the state. It features a collection of nearly 32,000 artworks across four floors, including modern and contemporary pieces, as well as notable architecture. The collection spans from ancient times to the present and includes European and American paintings, sculptures, prints, drawings, decorative arts, photographs, and folk art.

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General MacArthur was the top cadet of West Point's 1903 class. This sculpture honors him for his leadership in the Pacific during World War II. MacArthur, his father, and his grandfather were all Milwaukee residents. His last visit to the city was on April 27, 1951, when he received an honorary degree from Marquette University.

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The Milwaukee Art Museum is known for its striking architecture, especially the Burke Brise Soleil, which opens and closes like wings. Don’t miss the stunning views of Lake Michigan from the museum’s café. With rotating exhibitions and an impressive permanent collection, it’s worth taking your time to explore both the art and the building itself.

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Take a short break during your ride and enjoy sweeping views of Lake Michigan with a fresh breeze.

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Frequently Asked Questions

How many touring cycling routes are available in Shorewood?

Shorewood offers a wide selection of touring cycling routes, with over 40 options available. These routes cater to various skill levels, including more than 30 easy routes and 10 moderate routes, ensuring there's something for every cyclist.

What is the best time of year for touring cycling in Shorewood?

The best time for touring cycling in Shorewood is generally from spring through fall. The region experiences pleasant weather during these seasons, ideal for exploring the scenic Lake Michigan shoreline and Milwaukee River banks. While winter cycling is possible, conditions may vary due to snow and ice.

What are the general terrain and surface types like for cycling in Shorewood?

Shorewood's cycling routes primarily feature gentle gradients, especially along the Lake Michigan shoreline and Milwaukee River. The extensive network, including the Oak Leaf Trail, is largely paved, offering smooth surfaces. Some connecting trails, like the Bugline Trail, may include crushed limestone sections, providing a diverse riding experience through woodlands and urban parkland.

Are there easy touring cycling routes suitable for beginners in Shorewood?

Yes, Shorewood is very beginner-friendly, with over 30 easy touring cycling routes. A great option for an accessible ride is the Veterans Park Lagoon – Lakeshore State Park loop from Whitefish Bay, which is 15.5 miles (24.9 km) long and offers beautiful views of Lake Michigan and urban parkland.

Are there more challenging touring cycling routes around Shorewood?

For cyclists seeking a longer, more challenging experience, Shorewood offers several moderate routes. The Oak Leaf Trail loop — Southern Milwaukee is a notable option, covering 51.8 miles (83.3 km) and exploring a significant portion of the comprehensive Oak Leaf Trail system.

Are there any circular touring cycling routes in Shorewood?

Yes, many of Shorewood's touring cycling routes are designed as loops, allowing you to start and end at the same point. Examples include the Veterans Park Lagoon – Lakeshore State Park loop from Whitefish Bay and the Lakeshore State Park – Milwaukee Art Museum loop from Riverwest, which offers a 19.5-mile (31.4 km) ride through urban landscapes and along the lakefront.

Are there family-friendly touring cycling routes in Shorewood?

Shorewood is an excellent destination for family-friendly cycling. The extensive Oak Leaf Trail system, easily accessible from Shorewood, provides paved, safe routes suitable for all ages. Parks like Atwater Park and Hubbard Park also offer pleasant environments for family outings.

What scenic viewpoints or natural features can I expect along Shorewood's cycling routes?

Cycling in Shorewood offers numerous scenic viewpoints and natural features. You'll encounter breathtaking views of Lake Michigan along the shoreline, especially near Bradford Beach and Pebble Beach. The Shorewood Nature Preserve provides a tranquil escape with its woodlands and bluffs, while the Milwaukee River banks offer a 'north woods river retreat' feel, particularly around Hubbard Park.

Are there any interesting landmarks or attractions to see while cycling in Shorewood?

Absolutely. As you cycle, you can spot landmarks like the historic Milwaukee Pierhead Lighthouse and the iconic North Point Water Tower. The Milwaukee Art Museum is also a prominent feature along some lakefront routes, offering a cultural highlight to your ride.

Where can I find parking for touring cycling routes in Shorewood?

Shorewood's bike-friendly infrastructure includes various access points to its trail network. Parking is generally available near major parks like Atwater Park, Estabrook Park, and Hubbard Park, which serve as convenient starting points for many routes. Specific parking details can often be found on local park websites or within individual route descriptions.

Is public transport accessible to Shorewood's bike trails?

Yes, Shorewood's commitment to sustainable transportation means its bike trails are well-integrated with public transport options. Many local bus routes serve the Shorewood area, providing access to various trailheads and parks. Cyclists can often transport their bikes on buses, making it easy to reach starting points without a car.

Are there places to eat or drink along the touring cycling routes in Shorewood?

Yes, Shorewood offers several convenient spots for refreshments. Hubbard Park, located on the Milwaukee River, features the rustic Hubbard Park Lodge with a restaurant and beer garden, perfect for a mid-ride break. Additionally, Shorewood's vibrant community means you'll find various cafes, restaurants, and local markets easily accessible from the main cycling routes.

What do other touring cyclists enjoy most about cycling in Shorewood?

The touring cycling experience in Shorewood is highly rated by the komoot community, with an average score of 4.9 stars from over 27 reviews. Cyclists frequently praise the region's extensive network of bike trails, the stunning views of Lake Michigan, and the diverse natural settings that blend urban landscapes with serene woodlands and riverbanks.

Most popular routes around Shorewood

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