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Wisconsin Rail Trails Bike Tour 01
Wisconsin Rail Trails Bike Tour 02
Wisconsin Rail Trails Bike Tour 03
Wisconsin Rail Trails Bike Tour 04
Wisconsin Rail Trails Bike Tour 05

6-Day Wisconsin Rail Trails Bike Tour

Roll through Wisconsin on a 6-day rail trails bike tour. Smooth paths, friendly trail towns, and relaxed daily mileage with dependable support.

Start - End: Milwaukee - Milwaukee

Total trip: 6 days

Average group size: 12 people

from USD 3,599/pp including taxes and fees

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Trip Inquiry - 6-Day Wisconsin Rail Trails Bike Tour

Wisconsin Rail Trails Bike Tour 01
Wisconsin Rail Trails Bike Tour 02
Wisconsin Rail Trails Bike Tour 03
Wisconsin Rail Trails Bike Tour 04
Wisconsin Rail Trails Bike Tour 05
Wisconsin Rail Trails Bike Tour 01
Wisconsin Rail Trails Bike Tour 02
Wisconsin Rail Trails Bike Tour 03
Wisconsin Rail Trails Bike Tour 04
Wisconsin Rail Trails Bike Tour 05
Wisconsin Rail Trails Bike Tour 06
VIEW DATES

Trip Inquiry - 6-Day Wisconsin Rail Trails Bike Tour

Enter your details below, and we'll send the itinerary straight to your inbox!

Roll through Wisconsin on a 6-day rail trails bike tour. Smooth paths, friendly trail towns, and relaxed daily mileage with dependable support.

With over 2,000 miles of rail trails, Wisconsin is a cyclist’s dream. On this 6-day tour, you pedal five scenic trails: Glacial Drumlin, Glacial River, Sugar River, Badger State, and Military Ridge. Spin along these quiet routes and explore glacier-sculpted landscapes, prairie meadows, sparkling rivers, and historic towns. Cultural highlights include staying in the village of New Glarus — which retains the charm of a Swiss Alpine village. You can also visit two amazing architectural sites: the famous Frank Lloyd Wright home called "Taliesin", and the eclectic and surreal "House on the Rock". Finish with a visit to Cave of the Mounds, a National Natural Landmark with stunning limestone formations.


Surfaces for this tour: 65% Crushed Limestone, 35% Paved

Trip Highlights

Itinerary

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After brief introductions, we'll take a short shuttle, arrive at the trailhead of the Glacial Drumlin Trail. You cycle past glacial features called drumlins — low-lying hills created by the massive sheets of ice that passed over Wisconsin in the last Ice Age. Along the way, look for sandhill cranes perched on the remains of old railroad bridges with their wooden pilings now slowly disappearing into the wetlands below. Wrap up your ride near Lake Mills, then shuttle to the Best Western in Jefferson, our home for the night.

Relax before heading out for a celebratory dinner at a nearby brewing company.
Accommodation: Best Western Plus Jefferson 
Meals: Lunch, Dinner

Biking: 45 miles (72.4 kilometers)
Elevation Gain/Loss: 1,073 feet (327 meters) ascent, 1,031 feet (314 meters) descent
Terrain: Intermediate 

After a hearty breakfast, load up and shuttle to the start of the Glacial River Trail. This ride takes you through serene farmland, across wooden bridges, and past Native American effigy mounds. You have the chance to pedal through a beautiful covered bridge, and you’re on your own for lunch - there are plenty of options en route.

At the end of the day, shuttle to the Chalet Landhaus Inn in New Glarus, a Swiss-inspired town settled in 1845. Dine together with the group tonight at the inn’s charming restaurant. 
Accommodation: Chalet Landhaus Inn, New Glarus
Meals: Breakfast, Dinner

Biking: 46.3 miles (74.5 kilometers)
Elevation Gain/Loss: 1,115 feet (340 meters) ascent, 1,099 feet (335 meters) descent
Terrain: Intermediate 

Today’s ride follows the Sugar River Trail, designated a National Recreational Trail. You cross 14 trestle bridges and pass through tranquil countryside. Whether you choose a shorter one-way ride or a full out-and-back, you have time to explore New Glarus. 
In the afternoon, tour the Chalet of the Golden Fleece, home to one of the most curious collections in the Midwest.

Dinner tonight is just a short walk from the inn. 
Accommodation: Chalet Landhaus Inn, New Glarus
Meals: Breakfast, Dinner

Biking: 43.4 miles (69.8 kilometers)
Elevation Gain/Loss: 841 feet (256 meters) ascent, 840 feet (256 meters) descent
Terrain: Easier or Intermediate 

After breakfast, pack up and shuttle to the Badger State Trail, which winds through farmlands, rolling hills, and scenic meadows. You pass through small towns and scenic vistas before ending your ride in Madison. (Note: the Stewart Tunnel along the trail is currently closed. A detour is used until the tunnel reopens.)

You check into the The Edgewater, Madison for the next two nights. Tonight is yours to explore and enjoy Madison’s lively dining scene. 
Accommodation: The Edgewater, Madison
Meals: Breakfast

Biking: 39 miles (62.8 kilometers)
Elevation Gain/Loss: 1,020 feet (311 meters) ascent, 1,122 feet (342 meters) descent
Terrain: Intermediate 

Today, you swap the bike saddle for visits to two architectural and artistic wonders. After breakfast, shuttle to Spring Green for a tour of Taliesin, Frank Lloyd Wright’s historic estate. After lunch at the Spring Green General Store, explore the wildly whimsical House on the Rock, a maze of fascinating collections and surreal design. Riders who prefer to explore Madison on their own can opt to ride the Capital City Trail, accessible from the hotel.

Back in Madison, gather for a final group dinner at Eno Vino, a local favorite restaurant with stunning views.  
Accommodation: The Edgewater, Madison
Meals: Breakfast, Dinner

Biking (Optional): 19.4 miles (31.2 kilometers)
Elevation Gain/Loss: 610 feet (186 meters) ascent, 612 feet (187 meters) descent
Terrain: Easier 

Load up luggage after breakfast and set off on your final ride: the Military Ridge Trail. This scenic rail trail once served as a military route and today winds through woodlands, wetlands, and prairie as it traces the Sugar River. 
Your final stop is Cave of the Mounds, a National Natural Landmark with stunning limestone formations.

You enjoy a picnic lunch, explore the cave’s colorful depths, then shuttle back to Courtyard by Marriott Milwaukee Airport for farewells. 
Accommodation: Not applicable
Meals: Breakfast, Lunch

Biking: 28 miles (45.1 kilometers)
Elevation Gain/Loss: 940 feet (286 meters) ascent, 496 feet (151 meters) descent
Terrain: Intermediate 
 

Inns

Chalet Landhaus Inn - Wisconsin Rail Trails Bike Tour

Chalet Landhaus Inn, New Glarus

The Chalet Landhaus Inn blends Swiss charm with warm Midwestern hospitality, offering cozy alpine-style rooms, hearty homemade breakfasts, and a welcoming spot to unwind in the heart of New Glarus.

Best Western Plus, Jefferson

A warm welcome awaits at the Best Western Plus Jefferson Inn — comfortable, well-appointed rooms in the heart of southern Wisconsin. It's a great base for exploring the region's scenic trails and rich history, with everything you need for a relaxed, enjoyable stay between rides.

The Edgewater (Madison)

The Edgewater, Madison

The Edgewater in Madison offers a refined lakeside escape, where elegant rooms, exceptional dining, and stunning views of Lake Mendota come together just steps from the vibrant heart of the city. It is perfect for your relaxing stay with a touch of luxury.

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Frequently Asked Questions

We know you might have a few questions before you book. Our frequently asked questions cover everything you need to know to feel ready for the ride.

On the first morning of the tour please meet at the Courtyard by Marriott Milwaukee Airport at 8:30 am. You are welcome to book your pre-tour stay at this hotel directly or any other hotel in Milwaukee, though you must make your own way to the pick-up point at the pre-designated time.

Your tour ends with a drop-off back at the Milwaukee Mitchell International Airport or Courtyard by Marriott Milwaukee Airport at 4:30pm.
 

Arrival: We recommend arriving in Milwaukee at least the day before your tour starts. Many guests like to arrive a day or two early to accommodate potential flight delays and/or explore the city prior to your tour start.

Departure: Flying out on the last day of the tour, we recommend departing from Milwaukee after 6pm. Earlier flight times will require a separate transfer booked at your own expense.

If you plan to drive to the tour’s pick-up location, please ensure you arrange parking for the duration of your tour. If the pick-up point is a hotel, we recommend contacting them directly to inquire about parking availability. Keep in mind some hotels do not permit non-guests to park on-site, so you may need to find alternative parking options.

You’ll be fully supported throughout the tour with two experienced tour leaders — one riding alongside the group and another following in a support vehicle. The support van travels with you on all riding days, stocked with snacks and tools, and ready to help with repairs or provide a lift whenever needed.

Your tour leaders are there for more than just the cycling. They’re happy to assist with logistics, help arrange transport, and share local insights and recommendations to help you make the most of each stop along the way.

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What's included

  • 5 nights’ accommodation
  • 5 breakfasts, 3 lunches, 4 dinners
  • Our own highly experienced trip leaders, with you from start to finish
  • Industry leading Guest-to-Guide ratio (averaging 6:1)
  • Your own ‘Account’, an online space with everything required for your adventure
  • Our knowledgeable Customer Service Team to answer your queries - just a phone call, email or chat away
  • Customer Service pre-trip phone calls to ensure you’re 'trip ready'
  • Delicious snacks and non-alcoholic drinks to keep you fueled
  • Gravel bikes with drop handlebars, Hybrid with flat-bar handlebars or E-Bikes, equipped with a front handlebar bag or rear carrier, branded water bottle, mirror and flat pedals
  • Ride with GPS for navigation along with the detailed maps and itineraries
  • Branded t-shirt and bag
  • All activities outlined in the itinerary
  • All necessary equipment (well-maintained and safe) for activities
  • Transportation in our air-conditioned vans - safe, clean, modern and comfortable!

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