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Road cycling routes
United States
Wisconsin
Milwaukee County

Greenfield

The best road cycling routes around Greenfield

4.6

(31)

1,640

riders

86

rides

Road cycling routes around Greenfield are characterized by diverse terrain, ranging from flat, paved paths to routes with significant elevation changes. The area features a mix of urban and natural landscapes, including shorelines and park systems. Cyclists can find routes that traverse along rivers and through various community parks.

Best road cycling routes around Greenfield

  • The most popular road cycling route is Grant Park Beach – Oak Leaf Trail — Shore line loop from Milwaukee Airport, a 50.3 miles…

Last updated: June 2, 2026

46

riders

#1.

Grant Park Beach – Oak Leaf Trail — Shore line loop from Milwaukee Airport

81.0km

03:56

320m

320m

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

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Moderate

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

Moderate
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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

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

Moderate
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Tips from the Community

David Howells
June 28, 2025, Hank Aaron Trail

This 15.6 mile shared used paved trail is named after the baseball legend Hank Aaron. It provides a continuous connection between American Family Field, home of the Milwaukee Brewers, and the Lake Michigan lakefront.

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The Hank Aaron State Trail runs alongside the Menomonee River, and at this point, you can access a viewpoint with nice views of the river and the small greenbelt surrounding it.

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This small pond is located in Three Bridges Park. It’s an easy short detour while cycling the Hank Aaron State Trail, offering a nice spot to take a break by the water.

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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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North Wahl Avenue glides along the shore of Lake Michigan while passing Bradford Beach, North Point Lighthouse, and Lake Park. It's only a short distance but the views from this stretch of road are sure to be a highlight of your ride.

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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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Frequently Asked Questions

How many road cycling routes are available around Greenfield?

Greenfield offers a wide variety of road cycling routes, with over 90 different tours available. These routes cater to various skill levels, from easy scenic rides to more challenging excursions through the region's diverse terrain.

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

Yes, Greenfield is well-suited for easy and family-friendly road cycling. The area features numerous flat, paved rail trails like the Canalside Rail Trail and the Riverside Community Bike Path. For a specific easy route, consider the Highland Memorial Park – New Berlin Recreation Trail loop from New Berlin, which is about 15.8 miles long and leads through park areas.

What kind of terrain can I expect on road cycling routes in Greenfield?

Road cycling in Greenfield offers diverse terrain. You'll find flat, paved paths ideal for leisurely rides, especially along the Connecticut River Valley and rail trails. However, the region also features challenging routes through the 'hilltowns' of Franklin County, offering significant climbs and rewarding views for more experienced cyclists.

Are there any challenging road cycling routes for experienced riders?

Absolutely. For experienced riders seeking a challenge, Greenfield and the surrounding Franklin County offer routes with substantial hills and elevation gains. Events like the Deerfield Dirt Road Randonnée (D2R2) highlight the area's potential for rugged and demanding rides. A moderate route to explore is the Hoyt Park Footbridge – Lincoln Park loop from Milwaukee Airport, which covers 66.6 miles with over 1300 feet of elevation gain.

What scenic viewpoints or landmarks can I see along road cycling routes?

Greenfield's routes offer many scenic viewpoints and landmarks. You can enjoy beautiful vistas of the Connecticut River Valley, especially impressive in autumn. Notable attractions include the Hoyt Park Footbridge, the Milwaukee Pierhead Lighthouse, and the Pebble Beach. Many routes also traverse through extensive park systems and along shorelines, providing picturesque backdrops.

What do other road cyclists enjoy most about cycling in Greenfield?

The komoot community highly rates road cycling in Greenfield, with an average score of 4.6 stars from over 24 reviews. Cyclists often praise the diverse terrain, which includes both scenic shoreline paths and challenging routes, as well as the extensive park systems and dedicated recreation trails that offer varied scenery and options for all ability levels.

Are there any circular road cycling routes around Greenfield?

Yes, many road cycling routes around Greenfield are designed as loops, allowing you to start and end at the same point. An example of a popular circular route is the Grant Park Beach – Oak Leaf Trail — Shore line loop from Milwaukee Airport, which is a moderate 50.3-mile ride.

What is the best time of year for road biking in Greenfield?

The spring, summer, and fall months generally offer the best conditions for road biking in Greenfield. The Connecticut River Valley is particularly stunning in autumn with vibrant foliage. While winter cycling is possible, routes may be affected by snow and ice, requiring appropriate gear and caution.

Are there any routes that pass by lakes or beaches?

Yes, several routes in Greenfield feature beautiful lakes and beaches. The region's extensive shoreline paths provide access to areas like Pebble Beach, Grant Park Beach, and the Lakeshore State Park. The Oak Leaf Trail — Shore line – Pebble Beach loop from Milwaukee Airport is a great option to experience these coastal views.

What are some notable trails or paths for road cyclists in the area?

Beyond the general road network, Greenfield offers dedicated paths like the Canalside Rail Trail and the Riverside Community Bike Path, which are excellent for road cyclists. The Hank Aaron State Trail is another significant path that provides a great cycling experience.

How long are the road bike routes near Greenfield typically?

The length of road bike routes near Greenfield varies significantly. You can find shorter loops, such as the Hank Aaron State Trail – Hank Aaron Trail loop from Alverno College at about 16.9 miles, to much longer, more challenging rides like the Hoyt Park Footbridge – Lincoln Park loop from Milwaukee Airport, which extends over 66 miles.

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