Wisconsin Wanderlust Rail Trail Bike Tour

Come discover and explore  Central Wisconsin on this six day bike tour!

Enjoy 6 car free days on this rail-trail ride between Lake Michigan and the Mississippi River in the heart of Wisconsin; including a day on the famous Elroy-Sparta Trail. This trail is famous as it is the first rails-to-trails project in the US, completed in 1965.  Since then, Wisconsin has built over 1,800 miles of rail trails. It’s time to go explore Wisconsin’s efforts while enjoying the sights, towns, and beauty of this mid-western state.


You will ride the Ozaukee Interurban Trail, Glacial Drumlin State Trail, Badger State Trail, Sugar River State Trail, Military Ridge State Trail, Capital City Trail, Elroy-Sparta State Trail, Great River State Trail and more!

Tour Highlights

Downtown Milwaukee

Glacial Drumlin State Trail

Elroy-Sparta Rail Trail

New Glarus Brewing

Lodging Options

Washington House Inn - Night 1

The Edgewater Madison - Nights 2, 3 & 4

The Charmant Hotel - Night 5

Day 1:   

The first day will be spent exploring Milwaukee, starting on the shores of Lake Michigan traveling north towards the town of Cedarburg. Our ride includes the Ozaukee Interurban Trail, which was once an electrified trolleyway that ran between Milwaukee and Sheboygan.


You will enjoy a night at The Washington House Inn – a  Select Registry B&B in Cedarburg.


Day 2: 

A short shuttle ride brings us to the Glacial Drumlin State Trail which opened in 1986 and follows the old Chicago and North Western Railway track. This trail provides a glimpse into the past when glaciers bore down on southeastern Wisconsin in the last Ice Age. Keep your eyes open for Drumlins, low, teardrop-shaped hills formed by rock and sand moving under glaciers. The trail passes through wetlands and rivers. Some of the wildlife frequently seen include large sandhill cranes, deer, wild turkeys, foxes, and other critters. Sixteen wooden bridges are situated along the trail; of these, two are more than 300 feet long!


The trail concludes in Cottage Grove where we will take a short shuttle to Madison.  The lovely “Edgewater” in Madison will be our base for three nights.


Day 3:  

A day to explore! Madison has a lot to offer. From The Edgewater we will ride the Military State Trail out to Mt. Horeb for lunch. Since we’re exploring Wisconsin, there better be some cheese and ice cream involved! We will stop for a tour of the Babcock Hall Store for Dairy and Ice Cream; this gem is run by the University of Wisconsin Agricultural Department. Enjoy a relaxing day of exploring and then head out to town for dinner on your own.


Day 4:

Again we’ll depart from The Edgewater, hopping on our bikes to pedal our way along the Badger State Trail to the town of New Glarus.  Settled in 1845 by Swiss immigrants, this picturesque community is a showcase of Swiss heritage, architecture, customs, and cuisine. New Glarus residents observe Swiss traditions throughout the year; you may hear yodeling and alphorns in a village famous as “America’s Little Switzerland.” It’s a great place to refuel with a stop at New Glarus Brewing, lunch in town, and plenty of chocolate and ice cream to be enjoyed!


The Badger State Trail travels 40 miles between Madison and the Wisconsin-Illinois border while traversing farmlands, woods, rolling hills, scenic meadows, remnant prairies, ravines, glacial topography, and several small communities. Highlighting the trail is the 1,200-foot long Stewart Tunnel. The tunnel is unique because it is built on a curve and visitors cannot see the other end when first entering the tunnel. We’ll ride the Badger State Trail to the intersection of the Sugar River State Recreation Trail which will take us directly to New Glarus.


Day 5:

This is it! Finally the day has come to ride the granddaddy of all rail-trails – the Elroy-Sparta. We will shuttle to the trailhead in Elroy after breakfast to begin this ride.


The Elroy-Sparta State Trail remains one of the most popular trails in the country. With three rock tunnels and five small towns along its 32.5-mile route, the trail is a favorite bicycling destination. The trail stretches through communities and passes by wetlands, prairies, farmland, and non-glaciated areas (the Driftless Area).  Three railroad tunnels highlight the trail which are each over 140 years old.


Lodging for your final night is at the The Charmant Hotel – a Luxurious Boutique Hotel In The Heart Of La Crosse. The hotel is a renovated candy factory, built in 1898.  Architectural details of the original building have been preserved and re-imagined, including maple wood flooring, wood beams, and exposed brick, some say that the sweet smell of candy still emanates from the bones of the building.  The group will stroll to town to enjoy a final group dinner together. Be sure to wander down from the hotel to the banks of the mighty Mississippi River!


Day 6: 

Your final ride departs from the hotel along the Mississippi and heading to the Great River State Trail. The trail travels through prairies and backwaters of the upper Mississippi River Valley. Built on an abandoned Chicago-Northwestern railroad line, the trail has a finely crushed limestone surface and passes through two National Wildlife Refuges.


The trail is in Wisconsin’s scenic Coulee Region, part of the Driftless Area that was untouched by glaciers during the last Ice Age. Visitors to the Great River Trail will enjoy the changing wetlands of the Mississippi River backwaters, 500-foot bluffs, hardwood forests, unique sand prairies and oak savannahs.


Twenty-one miles later you’ll arrive at The Historic Trempealeau Inn Restaurant in the town of Trempealeau. Pro-tip: Try the Walnut Burger! Following lunch we’ll load up in the van for the final shuttle – the return ride to Milwaukee. It’s time for farewells.

I love the fact that each bike is outfitted with a Garmin with the route for each day pre-programmed so it’s ok if the group gets spread out a bit. We were all together but still had a sense of ‘freedom’

Bill B  Saint Paul, Minnesota

Trip Information


Trip Length - Days

Tour Type
Rail Trail
Tour Rating
New York Finger Lakes Bike Tour Elevation
View Trip Profile

Daily Mileage

Check In Location
Milwaukee, Wisconsin
Wisconsin Wanderlust bike tour map
Tour Area
SAG Vehicle New York Finger Lakes Bike Tour
Support & Gear Vehicle

Minimum Age


5 Breakfasts | 6 Lunches | 3 Dinners

  • PP Double Occupancy

  • Single Supplement*

  • Bike Rental


*This is required if you are traveling solo or if you are traveling with someone but require separate beds.


Select your departure date and click to reserve your bike tour!

  • 2019 Dates
  • If your desired date is no longer available, to be placed on a waitlist, please follow the ‘Request Itinerary’ button below & send us a message or call our office number below to speak to one of our reservation staff. We may open additional tours, and those on the waitlist receive priority on future tours