Five Points Historic District – Glacial Drumlin State Trail loop from Waukesha

Bike touring routes & trails

Five Points Historic District – Glacial Drumlin State Trail loop from Waukesha

Moderate

4.7

(2500)

7,146

riders

Five Points Historic District – Glacial Drumlin State Trail loop from Waukesha

02:23

41.2km

180m

Cycling

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels. The starting point of the route is accessible with public transport.

Last updated: September 25, 2026

Waypoints

Start point

Bus stop

Get Directions

382 m

Five Points Historic District

Highlight • Historical Site

The Five Points Historic District in Waukesha, at the intersection of Broadway, Main St., and Grand Ave, showcases the history of some of the city's most iconic buildings. Post-1857, the …

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779 m

Veterans Park

Highlight • Monument

The park is a tribute to veterans and a cherished community gathering area. This is a good spot to take a break and enjoy the serene surroundings in this urban park.

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11.5 km

The Glacial Drumlin State Trail stretches 53 miles from Cottage Grove to Waukesha, offering a scenic journey through southeastern Wisconsin's glacial history. Formed during the last Ice Age, this area …

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18.3 km

Cushing Park Road Recreational Trail (Route of the Badger)

Highlight (Segment) • Trail

The Cushing Park Road Recreational Trail, part of the Route of the Badger, stretches for 3 miles. Though short, it serves as a crucial link in the regional trail system, …

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20.8 km

Lapham Peak

Highlight • Viewpoint

Lapham Peak formed over 10,000 years ago when a glacier covered vast swathes of Wisconsin. It's a perfect destination for hiking and cross-country skiing. Located in Kettle Moraine State Forest, it's open from dawn until dusk daily.

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25.1 km

Ice Age Trail – Lapham Peak Segment

Highlight • Trail

28.2 km

Wooden Bridge Over Trail

Highlight • Bridge

Just east of Wales, Wisconsin is this bridge over the trail. This is where the climb ends as you are heading west.

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40.5 km

Grede Park (Parade Memorial)

Highlight • Monument

This riverside park's primary focus is the Waukesha Parade Memorial, dedicated to lives lost and support of those surviving from the 2021 Christmas Parade Tragedy.

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