By Jason McDowell Creative Director Published Jun 13, 2023 at 3:01 PM

Pack your panniers and fill your water bottles: Here is your one-stop shop for riding from Milwaukee to any of the 11 days of the Kwik Trip Tour of America's Dairyland, which takes place between June 15-25.

Each route includes a RideWithGPS map that can be downloaded and used for turn-by-turn instructions. All routes start from a Milwaukee County Park with convenient parking. These are one-way routes, so if you're planning on making it a round trip, remember to double everything.

For routes that make use of state trails, don't forget to pick up your Wisconsin State Trail Pass.

At the bottom there is also a point-to-point map, for those who want to ride all 420 miles, from one location to the next.

Many of these routes have been created through the helpful assistance from Kelly Lambeth, general manager of Wheel & Sprocket in Bay View. (She also happens to be my wife.)

Day 1: Janesville

Map from Greenfield Park to Janesville ToADX

Much of your travels can be covered by off-street bike trails, including the Oak Leaf Trail, Hank Aaron Trail, New Berlin Interurban Trail, Glacial Drumlin Trail, Glacial River Trail, and the Ice Age National Scenic Trail.

RideWithGPS map: Greenfield Park to Janesville
Distance: 75 miles
Elevation: 1,700 feet

Day 2: East Troy

Map from Greenfield Park to East Troy ToADX

Spend some time on the Root River Parkway, Franklin's Hike and Biking Trail, but you'll mostly be on beautiful back roads for this one.

RideWithGPS map: Greenfield Park to East Troy
Distance: 40 miles
Elevation: 1220 feet

Day 3: Grafton

Map from Estabrook Park to Grafton ToADX

Almost the entirety of this route can be ridden on the Oak Leaf and Ozaukee Interurban trails.

RideWithGPS map: Estabrook Park to Grafton
Distance: 18 miles
Elevation: 420 feet

Day 4: Manitowoc

Map from Estabrook Park to Manitowoc ToADX

The route to Sheboygan is largely on the Ozaukee Interurban and Sheboygan Interurban trail and routes through Kohler-Andre State Park. After, you'll stick close to Lake Michigan until you reach Maritime Drive.

RideWithGPS map: Estabrook Park to Manitowoc
Distance: 85 miles
Elevation: 1800 feet

Day 5: De Pere

Estabrook Park to De Pere ToADX

The longest route of the series takes advantage of the Oak Leaf Trail and the Ozaukee Interurban Trail to get you as far as Cedarburg, then jogs slightly west to connect to the Eisenbahn State Trail all the way up to Eden.

Trails disappear around Lake Winnebago (which feels like a missed opportunity) but eventually connects back to the Fox River Trail, which takes you the rest of the way into De Pere.

RideWithGPS map: Estabrook Park to De Pere
Distance: 119 mi
Elevation: 3,000 ft

This route was created with insights from Tristan Klein, co-owner of the former Coast In Bikes.

Day 6: West Allis

Map of Estabrook Park to West Allis ToAD
Estabrook Park to West Allis.
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Map of Humboldt Park to West Allis ToAD
Humboldt Park to West Allis.
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From the north, the Hank Aaron State Trail is your main off-street bike path to get to West Allis. From the south, the Kinnickinnic River Parkway will do a bit of the heavy lifting.

RideWithGPS map: Estabrook Park to West Allis
Distance: 14 miles
Elevation: 313 feet

RideWithGPS map: Humboldt Park to West Allis
Distance: 7 miles
Elevation: 228 feet

Day 7: Mount Pleasant

Map from Humboldt Park to Mount Pleasant ToADX

From Humboldt Park you can follow the Oak Leaf Trail to Grant Park and then you meander along the Oak Creek Parkway. After, the scenic back roads will take you past farmer stands to Mount Pleasant.

You can cut 10 miles off your route if you start in Grant Park instead.

RideWithGPS map: Humboldt Park to Mount Pleasant
Distance: 31 miles
Elevation: 850 feet

RideWithGPS map: Grant Park to Mount Pleasant
Distance: 21 miles
Elevation: 560 feet

Day 8: Bay View, Milwaukee

Map from Estabrook Park to Bay View ToAD
Estabrook park to Bay View.
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Map from Hoyt Park to Bay View ToAD
Hoyt Park to Bay View.
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From Estabrook Park, there are slightly more direct routes to Bay View, but this one ambles through scenic Lakeshore State Park before arriving at the race course.

The Hoyt Park route takes advantage of the parkways along the Menomonee River. You could also save some mileage by starting in Doyne Park instead.

RideWithGPS map: Estabrook Park to Bay View
Distance: 9 miles
Elevation: 150 feet

RideWithGPS map: Hoyt Park to Bay View
Distance: 10 miles
Elevation: 250 feet

Day 9: Shorewood

Map from Cupertino Park to Shorewood ToAD
Cupertino Park to Shorewood.
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Map from Hoyt Park to Shorewood ToAD
Hoyt Park to Shorewood.
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As with the Bay View route, there are more direct routes from Cupertino Park to Shorewood, but we've added some little diversions around Lakeshore State Park and Veteran's Park.

The Hoyt Park route takes advantage of the downhills of State Street, avoids having to climb out of downtown and is routed on low-traffic streets like Brown and the Fratney Bicycle Boulevard. (If you want an alternate route, check the reverse route to Wauwatosa below.)

RideWithGPS map: Cupertino Park to Shorewood
Distance: 11 miles
Elevation: 250 feet

RideWithGPS map: Hoyt Park to Shorewood
Distance: 11 miles
Elevation: 300 feet

Day 10: Downer Ave., Milwaukee

Map of Cupertino Park to Downer Ave. ToAD
Cupertino Park to Downer Ave.
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Map of Hoyt Park to Downer Ave. ToAD
Hoyt Park to Downer Ave.
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Map of Estabrook Park to Downer Ave. ToAD
Estabrook Park to Downer Ave.
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Since Downer Ave is so centrally located, we've created three routes from the north, south, and west.

RideWithGPS map: Estabrook Park to Downer Ave
Distance: 4 miles
Elevation: 100 feet

RideWithGPS map: Hoyt Park to Downer Ave
Distance: 9.5 miles
Elevation: 280 feet

RideWithGPS map: Cupertino Park to Downer Ave
Distance: 8.8 miles
Elevation: 230 feet

Day 11: Wauwatosa

Map of Estabrook Park to Wauwatosa ToAD
Estabrook Park to Wauwatosa.
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Map of Cupertino Park to Wauwatosa ToAD
Cupertino Park to Wauwatosa.
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Close out the series with these cruises up State Street, which is noted for its lighter traffic flow, or the Hank Aaron State Trail.

RideWithGPS map: Estabrook Park to Wauwatosa
Distance: 10 miles
Elevation: 310 feet

RideWithGPS map: Cupertino Park to Wauwatosa
Distance: 9.5 miles
Elevation: 250 feet

Complete point-to-point map

For those who want to ride the entire epic 11-day loop without having to reset back in the city every day, here is a point-to-point map covering all 420 miles, starting in Janesville and ending in Wauwatosa.

Point-to-point map for all stops on ToAD 2023X

RideWithGPS map: Point-to-point map
Distance: 418 miles
Elevation: 10,300 feet

Jason McDowell Creative Director

Jason McDowell grew up in central Iowa and moved to Milwaukee in 2000 to attend the Milwaukee Institute of Art and Design.

In 2006 he began working with OnMilwaukee as an advertising designer, but has since taken on a variety of rolls as the Creative Director, tackling all kinds of design problems, from digital to print, advertising to branding, icons to programming.

In 2016 he picked up the 414 Digital Star of the Year award.

Most other times he can be found racing bicycles, playing board games, or petting dogs.