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Routes
Road cycling routes
United States
Wisconsin
Milwaukee County

Hales Corners

The best road cycling routes around Hales Corners

4.8

(17)

751

riders

33

rides

Road cycling around Hales Corners, Wisconsin, is characterized by its expansive park system and well-maintained trail networks. The area features extensive green spaces, including Whitnall Park, the largest park in the Milwaukee County system. Cyclists will find diverse natural features, such as the Root River Parkway, which is integrated into many popular cycling routes. The terrain primarily consists of paved surfaces, offering varied experiences for road cyclists.

Best road cycling routes around Hales Corners

  • The most popular road cycling route…

Last updated: August 9, 2026

56

riders

#1.

Highland Memorial Park – New Berlin Recreation Trail loop from Nathan Hale High School

56.5km

02:22

180m

180m

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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Moderate

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy
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Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy
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Popular around Hales Corners

Hiking around Hales Corners

Cycling around Hales Corners

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Tips from the Community

Martin
August 20, 2026, Grant Park Beach

The cobalt blue background of Lake Michigan provides a nice backdrop and gives the impression of bing in some places tropical during the summer months. The combination of Grant Park Beach along with Oak Leaf Trail offers a multitude of outdoor activities.

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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 cafes to stop at if you'd like to stay a while.

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As you cycle by Highland Memorial Park on the New Berlin Recreation Trail, you'll notice a peaceful and serene environment. This section of the trail offers a refreshing change with well-maintained grass and lush green trees, providing a picturesque backdrop to your ride. The tranquil atmosphere makes it a perfect spot to slow down and enjoy the scenery.

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The New Berlin Recreation Trail is a 7-mile paved path running east-west from New Berlin to Waukesha in the Milwaukee suburbs. Although it lacks trestles and tunnels, it’s popular among commuters for its convenience and speed, following power lines. Starting at Lincoln St., the trail heads east with a 3-mile stretch free of street crossings. It runs parallel to an active railroad, maintaining a safe distance. Highlights include a bike shop and cafes at Calhoun St., restrooms at Buena Park, and the scenic Gatewood Park further along.

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Alex
January 29, 2024, Oak Leaf 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.

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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 area to keep an eye out for birds and other wildlife.

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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 the beach from a number of different places, but the best option is to use the Oak Creak parking lot near Ferch's Beachside Grille. There are plenty of services here such as a playground and café, and you can walk right onto the beach.

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South Milwaukee Lagoon Pond is a popular fishing spot fed by Oak Creek (which flows out into Lake Michigan) along the Oak Creek Parkway in South Milwaukee, Wisconsin. This is a nice place to ride past as you explore the area.

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Frequently Asked Questions

How many road cycling routes are available around Hales Corners?

You'll find over 30 road cycling routes in the Hales Corners area, catering to various preferences. The majority, about 25, are classified as easy, while 7 offer a moderate challenge.

What kind of terrain and elevation can I expect on road cycling routes in Hales Corners?

The routes around Hales Corners primarily feature well-maintained paved surfaces, ideal for road cycling. While some segments might include unpaved or gravel sections for varied experiences, the area generally offers moderate elevation gains, making it accessible for different fitness levels.

Are there easy or family-friendly road cycling routes in Hales Corners?

Yes, Hales Corners is an excellent destination for easy and family-friendly road cycling. Many routes are classified as easy, such as the Highland Memorial Park – New Berlin Recreation Trail loop from New Berlin, which is 15.8 miles long and leads through well-maintained parkland. These routes often utilize the extensive green spaces and park systems, providing a pleasant and safe environment.

What natural features or landmarks can I see while road cycling in Hales Corners?

Road cycling routes in Hales Corners often pass through or near significant natural features and landmarks. You can explore the expansive Whitnall Park, which houses the tranquil Wehr Nature Center and the beautiful Boerner Botanical Gardens. The Hales Corners Park also offers well-maintained paths and a dog-friendly environment.

Are there longer road cycling routes for more experienced cyclists?

Yes, for those seeking a longer ride, routes like the Grant Park Beach – Oak Leaf Trail — Shore line loop from Mangan Woods offer a moderate challenge, covering nearly 68 kilometers with over 345 meters of elevation gain. Another option is the Little Menomonee River Parkway – Hoyt Park Footbridge loop from Valley View Park and Ride, which is almost 60 kilometers long.

What do other cyclists say about road cycling in Hales Corners?

The road cycling routes in Hales Corners are highly regarded by the komoot community, boasting an average rating of 5.0 stars from 5 reviews. Cyclists frequently praise the well-maintained trail networks, the scenic green spaces, and the diverse experiences offered by routes like the Oak Leaf Trail and Root River Parkway.

Are there circular road cycling routes available in Hales Corners?

Yes, many of the road cycling routes in Hales Corners are designed as loops, offering convenient starting and ending points. Examples include the popular Oak Leaf Trail loop from Franklin and the Hank Aaron Trail – Hoyt Park Footbridge loop from West Allis, allowing you to enjoy the scenery without retracing your path.

What is the best time of year for road cycling in Hales Corners?

The best time for road cycling in Hales Corners is typically from spring through fall (April to November), when the weather is mild and the natural landscapes are at their most vibrant. The Boerner Botanical Gardens, for instance, are open during these months, adding to the scenic beauty of the routes.

Are there amenities like cafes or restrooms along the road cycling routes?

While specific amenities vary by route, the Hales Corners area, with its numerous parks and proximity to urban centers, offers various opportunities for refreshments and restrooms. Many routes connect to or pass through areas where cafes, shops, and public facilities are accessible, especially near larger parks like Whitnall Park and Hales Corners Park.

Can I bring my dog on the road cycling trails in Hales Corners?

Many of the parks and multi-use trails in Hales Corners, including Hales Corners Park, are dog-friendly. However, it's always recommended to check specific trail regulations for leash requirements and any restrictions before heading out with your pet.

How can I access the broader trail network from Hales Corners?

Hales Corners is well-connected to the wider Milwaukee County trail system, most notably through the renowned Oak Leaf Trail. This multi-use path provides seamless access for cyclists, allowing you to connect to hundreds of miles of additional trails in surrounding counties and explore beyond the immediate Hales Corners area.

Where can I find parking for road cycling routes in Hales Corners?

Parking is generally available at various access points for the trail networks in Hales Corners. Many parks, such as Whitnall Park and Hales Corners Park, offer dedicated parking facilities. For specific routes, checking the starting point on komoot will often provide details on nearby parking options.

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