Running Between Madison And Milwaukee Is Wisconsin's Scenic State Trail Connecting 10 Lovely Small Towns

Wisconsin has some truly beautiful landscapes, and there's no better way to see them than from the seat of a bicycle. This bike-friendly state has over 1,000 miles of bicycle trails to choose from, but one of the best is the Glacial Drumlin Trail, running between Madison and Milwaukee. This 52-mile-long scenic trail connects Cottage Grove to Waukesha via a route through eight other lovely small towns. 

As a rail trail, the Glacial Drumlin Trail is mostly flat with a crushed stone surface, making it a fairly easy ride for most cyclists. There is an asphalt-paved section on the Waukesha end of the route for a few miles, and a section in Jefferson that isn't separated from traffic, but the rest of the trail is blissfully vehicle-free, so you're not constantly buffeted by passing cars or sucking down exhaust while you ride.

Rural countryside, serene lakes, and shade tree tunnels all grace the route at one stretch or another. Enjoy a day of exercise, cycling in the fresh air, without having to drive far from the city first. Thanks to Wisconsin's extensive trail system, it's easy to connect to other trails that feed right into the downtown areas of both Madison and Milwaukee. Besides the natural scenery, stopping in small towns along the way is also worthwhile. Several have cute eateries trailside or nearby, perfect for a little rest and pick-me-up before continuing on your journey through southern Wisconsin's open fields and forested wetlands.

The trail meanders through ten towns: Cottage Grove, Deerfield, London, Lake Mills, Jefferson, Helenville, Sullivan, Dousman, Wales, and Waukesha. Some are unassuming small towns, and others are fast-growing suburbs, connecting the state's two biggest urban areas with the quiet countryside after just a few miles' easy ride from either direction. Cottage Grove is one of Wisconsin's fastest-growing cities, 20 minutes east of Madison, the "Biking Capital of the Midwest," and Wisconsin's capital city. Waukesha anchors the eastern end of the trail, 30 minutes west of Milwaukee and Lake Michigan. 

In between, the other towns each offer something different, with cute boutiques, family-owned restaurants, and plenty of local parks for anyone who wants a quick break. Lake Mills has Korth Park, and the Jerzey Junction Ice Cream & Candy Shoppe, and Cottage Grove has the Olde Town Coffee House for breakfast or the 1855 Saloon and Grill for lunch or dinner. In Dousman, the Bicycle Doctor Nordic Ski Shop is right by the trail in case you need to fix anything that the trailside aid station can't fix. The trail ends at the Fox River Sanctuary in Waukesha. There's plenty to see along the route!

If you're more interested in the views than stopping in the towns, you have options. According to Reddit users, the most scenic stretch of the Glacial Drumlin Trail is between London and Lake Mills. In Lake Mills, the trail passes by Sandy Beach and over Rock Lake before coming to a spur trail that connects to Korth Park or continuing on the main trail to London. If you're looking for even more scenic places, the Military Ridge Trail has stunning scenery, which is on the other side of Madison and passes through two state parks.

The Wisconsin DNR trail map has lots of valuable information, like where major trailheads with parking are and what kinds of amenities are available at each one. Most have real flushing toilets, while a few have only vault toilets. Some have playgrounds or picnic areas, and others have no amenities at all. 

The map also provides distances between each town on the route, so you can choose your midpoint ahead of time without guessing at the mileage or save it to your phone and make a decision while out on the trail. The only thing it doesn't show in great detail is the section of trail in Jefferson that isn't separated from traffic. Signs direct users onto country roads to reconnect to the separated path on the other side of town, but you will be riding on the roadside shoulder in between. Be prepared for that if riding through Jefferson. Google Maps shows it pretty well if you think you missed a sign.

Before you head out for your ride, be prepared to pay for a trail pass. Biking or inline skating on the Glacial Drumlin trail requires a state trail pass, but walking or hiking on the same trail does not. A daily or annual trail pass is required for everyone aged 16 or older while using the trail. Buy passes online or at a kiosk at a trailhead.