Wisconsin Wanderlust Rail Trail Bike Tour

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

Enjoy 5 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, 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

Mt. Horeb

Miller Brewery

Lodging Options

The Charmont Hotel - Night 1

The Edgewater Madison - Nights 2 & 3

The Iron Horse Hotel - Night 4

Day 1:   

We begin the day with meeting everyone in Milwaukee before heading to the western side of Wisconsin. We’ll work away back across the state through the week. Our first day brings us to one of the riding highlights of this trip: 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.


Before starting the ride, we’ll enjoy lunch at The Historic Trempealeau Inn Restaurant in the town of Trempealeau. Pro-tip: Try the Walnut Burger!

Lodging for this first 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 2: 

A short shuttle brings us to today’s ride and the rail-trail that started it all: The Elroy-Sparta State Trail! It  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.

Tonight we transfer to Madison to enjoy our first of two nights at the lovely Edgewater Boutique Hotel located on the edge of Lake Mendota


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. Mt Horeb is well known for it’s Norwegian heritage and trolls will welcome you to town! Lining the streets, in stores, it’s where trolls play. We’ll enjoy lunch at the Grumpy Troll Brewery.

After you’ve taken in the charm of this small town, you will have the option of riding back to Madison should you want more miles on your bike, or returning with the van. Relax for the rest of the afternoon or set out to explore Madison.


Day 4:

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!

Tonight we’ll explore Milwaukee from the Iron Horse Inn


Day 5:

Wake up and say hello to Milwaukee! This city is full of places to explore. We’ll leave from the hotel by bike, heading to the Historic Third Ward and along the banks of Lake Michigan. We’ll end this day with a tour of the historic Miller Brewery before bidding our 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
Route Overview

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*

  • Standard 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!

  • 2021 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. If you would like a Private Tour, please fill out this request form, or call our office.