Please click here to jump to Pricing within the Overview section that includes all tour details.

We are excited to announce a brand new road biking tour for 2026 exploring the Midwest’s Driftless Region.

For the last decade, the cycling community has praised this area for its quiet roads and charming small towns. Following a meeting in 2024 between Lizard Head’s founder, John Humphries, and the Sinsinawa Mound Covent, we have developed a premier tour featuring world-class routes and comfortable, local hotels.

We invite you to join us as we explore this exceptional riding destination. Sign up today to secure your spot for our 2026 tour of the Driftless Region.

The Driftless Region Road Bike Tour: Highlights

The Driftless Region Natural History

The Driftless Region is a unique topographical and geological region, spanning the southwestern corner of Wisconsin, southeastern Minnesota, and northeastern Iowa. The region’s topography was established in the last ice age: the area was never covered by ice and therefore lacks the glacial deposits, known as “drift” that define much of the Midwest (hence, “driftless”).

As a result of this historical and geological quirk, the region’s landscape is not at all what one might expect of the Midwest. Instead of flat plains and broad fields, the Driftless Region is defined by steep hills, forested ridges, and deeply-carved river valleys.

This unique landscape makes the Driftless Region an exciting destination for cycling. In recent years local bike shops and event organizers have introduced the region’s riding options to a national audience (and, Trek bikes has proudly touted how critical the region has been in developing their own line of gravel bikes). In light of all of this hype, Lizard Head Cycling Guides cannot wait to run our first trips in the Driftless Region, and check out all the great cycling available!

The Sinsinawa Mound Center: Community-Driven Regenerative Agriculture in America’s Heartland

The Sinsinawa Mound Center was once home to one of the largest groups of Catholic Dominican Sisters in the Midwest. Now, while the campus is still home to a number of Dominican Nuns, much of the space has been devoted to a number of community initiatives, including the Sinsinawa Mound Collaborative Farm and the Fields of Sinsinawa learning center. On our tour, we’ll visit Sinsinawa Mound, tour the historic campus, and hear first-hand about the ways in which these initiatives are helping farmers across the Midwest, and across the world, share best practices, develop regenerative agriculture techniques, and fortify their own local food systems.

The Driftless Region Road Bike Tour: Dates

Potential tour dates are listed below and not all tour dates will run. Lock in your preferred tour date early as unopened tour dates will be closed. Please see the Spring/Autumn Tour Calendar and the Summer Tour Calendar for confirmed departures. Any unopened date can be a Custom Week (9 riders required). Please contact us via email or call 970.728.5891

2026 Tour Dates

• September 29 to October 4, 2026 (Book Now!)

• October 6 to 11, 2026 (Book Now!)

Tour Status Notes: NO STATUS = Date Set, no riders have signed up. TOUR OPENED = Tour Opened, rider minimums not met. TOUR A GO! = Tour is Go, rider minimums met. SOLD OUT = Tour Full, rider maximums met.

Why Should You Sign Up Now And OPEN A Tour Date?
This is the proverbial chicken and the egg conundrum! We need our cyclists to first commit to the date that works for them so we can commit to that date.

When you OPEN a date, you get to pick your preferred departure and there is no penalty if the tour does not run. Once you pick your tour date, Lizard Head closes nearby dates and funnels all additional riders to your chosen date until the tour meets the rider minimum. Don't wait. Just do it!

BONUS: As an added bonus, we can also hold a spot for you on another tour date of your choosing. There is no fee to switch to another tour date.

NOTE: In anticipation and encouragement of future tour sign-ups prior to reaching the tour minimum, the Lizard Head Cycling website may be updated to show TOUR A GO prior to actual tour confirmation. Even if the website says that the tour is a GO, please wait for your official Email Confirmation before booking non-refundable travel reservations.

The Driftless Region Road Bike Tour: Overview

Tour Length: 6-Days Cycling/5-Nights Lodging

Meeting/Ending Town/Hotel: Madison, WI – Dane County Regional Airport (MSN). The meeting/ending hotel will be provided in the tour documents after one completes registration.

Total Miles: 200 to 265 miles on mixed surfaces (additional mileage options available)

Ability Level: Intermediate (2/3) , Upper Intermediate (3) , Advanced (3/4)

Gravel Category Types: Below is a list of the various types of gravel surfaces. Most Lizard Head gravel tours fall within the Category 1 and Category 2 types of gravel surfaces with occasional sections of Category 3, or more rarely, Category 4.

• Category 1: Smooth, well-maintained dirt roads with little to no small gravel chunks
• Category 2: Dirt roads with potholes, washboards and loose corners
• Category 3: Poorly maintained roads with bigger rocks, ruts and/or sand
• Category 4: Non-maintained tracks or roads with deep layers of sharp gravel

Tour Cost: $3,695 per person. Add $695 per person to this Tour Cost for a private room each night of the tour (includes 5-Nights). Please see our Reptile Rewards & Tour Discounts page for more information on Group Discounts. Please note that for discounts to apply the tour minimum must be met.

Tour Includes: 6 days of guide service, 5 nights of accommodation, all meals from lunch on Day 1 through lunch on Day 6 aside from 1 dinner and 1 breakfast, energy food, liquid refreshments, shuttles, and mechanical support. Alcoholic beverages and bike rental are not included.

Lodging for 5 Nights: (subject to change)

• Night 1: Galena Inn or DeSoto House Hotel, Galena, IL
• Nights 2 & 3: Hotel Julien Dubuque or Redstone Inn and Suites, Dubuque, IA
• Night 4: Waterfront Hotel or River District Hotel, Prairie du Chien, WI
• Night 5: Steampunk Manor B&B, Spring Green, WI or Silver Star B&B, Avoca, WI

Meeting Hotel and Ending Hotel reservations and costs are NOT included unless specified otherwise. Guests are on their own to make reservations at the Meeting Hotel or Ending Hotel, or other nearby hotels.

Road Bike Rentals

The make, model, and specifications of rental bikes may differ from what is described below. Please contact us if you have any specific needs or have any questions about our rental bikes.

Lizard Head Cycling Guides is proud to rent Scott Bikes. The Scott Addict 10 Disc was designed from the ground up with those longer days in mind. With geometry that is less focused on racing and more on enduring, the Addict 10 will be your go-to when you’re looking to put the miles in.

The Scott Addict 10 Disc features: Carbon Frame and Fork, Shimano Ultegra 2x11 Drivetrain, 34x32 Compact Gearing, 30mm Tires, and Hydraulic Disc Brakes. Approx. Weight: 16.89 lbs / 7.66 kg (without pedals)

Road E-Bike Rentals

Click Here for more information on our Road E-Bike Rentals, including pricing. E-Bike rental availability is limited, so please reserve early. Although E-Bikes are great, our tours were originally designed to be ridden without motorized assistance. We keep our cyclists together with a variety of techniques, including staggered starts and "bumps" along the road.

If you have any further questions, please read more on our Rental Bikes FAQ page. You can also email us at info@lizardheadcyclingguides.com or call us at 970.728.5891

☛ Learn more about our Rental Bikes and Equipment

Meals On Tour

Lizard Head Cycling Guides provides most meals on all tours (unless otherwise noted), including breakfast, lunch, and dinner. Guides will prepare a daily lunch en route for nearly every tour, both road and off-road, as well as provide nutritious snacks at periodic aid stations during the day.

Most of our road tours utilize local restaurants for all meals and, occasionally, guides may prepare a dinner or two during a tour. Due to the nature of being "off the grid", most of our off-road tours feature guides preparing meals for breakfast, lunch, and dinner. FUN NOTE: When guides prepare a meal in camp and the guests sit around and watch, this is called "Guide TV".

We also pride ourselves on being able to cater to specific dietary requests and needs, so rest assured that you will be able to get the nutrition that works best for you during your tour. Gluten free, Dairy free, Vegan, or someone who loves it all – we will keep you well-fed during the tour!

Lunches: Lizard Head Cycling Guides prepare healthy lunches to keep you going. We will serve you fresh organic fruits and veggies, salads, hummus, sandwich fixings, nuts, gourmet cheeses and, of course, plenty of salty/sweet snacks such as chips and cookies.

Dinners: On our road tours, Lizard Head Cycling sources our favorite restaurants in each town that we visit. Our guides focus on establishments that offer fresh and local ingredients and guests choose whatever they desire to eat off the menu, including: appetizer, salad, entrée, and of course, dessert... yum! Also, while on tour, if a guest wants to dine early before the group and go to bed, this is fine. We understand that on some days, sleep is the most important post-ride element.

Ability Level: Can I Ride This Tour?

Definition of Ability Levels

= Intermediate (2/3) Rides and/or takes spin classes 1 to 3 times a week for a total of 50 or more miles.
= Upper Intermediate (3) Rides and/or takes spin classes 2 to 4 times a week for a total of 75 or more miles.
= Advanced (3/4) Rides and/or takes spin classes 3 to 5 times a week for a total of 100 or more miles. Has ridden multi-day tours and done a century ride.
= Expert (4) Rides 4 or more times per week totaling 150 or more miles. Rides E.F.I. with regularity. Has done numerous multi-day tours, century rides and races.

How Fit do I Have to Be? If one month prior to the tour, you can ride 2 to 3 times a week, equaling a total of 75 or more miles a week, you'll do just fine. We like to jokingly say that "one is ready for a Lizard Head Cycling Tour when they are finished with the tour" and this is true! The only way to simulate a week-long bike tour is to go on a week-long bike tour.

Our average rider age is 55 years. These are bike tours, not races, so we take our time to stop, take pictures and see the sights. We have all day to reach our destination and most riders take "bumps" at some point. We offer reduced mileage options for each day. Of course, if someone wants to ride E.F.I. (Every Freaking Inch), we love to show them all the extra climbs, loops and hidden canyons that can be included!

Do the Bump! Daily mileage options allow cyclists of varying abilities to enjoy this tour. One of our favorite options is to give cyclists a "bump" via the support vehicle, or a 10 to 20-mile lift down the road representing an hour of pedal time. After the bump, the rider is "off the front" and riding at his or her own pace without feeling they are being left behind the group. They'll then have time to linger and take in the spectacular scenery. All cyclists come together in time for lunch. Afterward, cyclists can take another bump and/or continue riding.

Seamless Mileage Options. Lizard Head Cycling Guides designs multiple mileage options for each tour – something we're well known for in our business. This technique is similar to heliskiing in that one does not ski everything, they ski the best. 🙂

Slow or Fast? Many cyclists who sign up for our tours have worried themselves silly about not being able to keep up, but then they're surprised to find that all the worrying was about nothing. They do just fine! Slow and Fast only exist relative to other cyclists. Speed does not matter as long as one is moving on the bike. As long as one is moving, they are truly going fast enough.

Questions? If you have questions about your ability to ride this tour, please contact our office via email or call us at 970.728.5891, we will be more than happy to guide you!

Please also see this blog post for more information.

Overall Route Map

Below is an example of the daily routes for this tour, which are subject to change based on season, available accommodations, road closures, and other factors. The actual routes will be made available to registered participants before their tour, so please view these routes as a general outline of what to expect.

The Driftless Region Road Bike Tour: Itinerary*

*PLEASE NOTE: Tour itineraries are subject to change and modification based on the group, available accommodations, road construction, road closures, and other unforeseen circumstances including weather, wildfires, flooding, hurricanes, landslides and/or other acts of nature. Also, the distances and elevation profiles shown below may not reflect the actual distances and elevations while on tour as these are provided here to give an idea as to the anticipated mileage and terrain. Please view this itinerary, the distances, and elevation profiles as a general outline of what to expect while on this tour.

Day 1: Sinsinawa Mound to Galena
27 miles with up to 1,500 feet of climbing (100% paved)

Starting early morning at our meeting hotel in Madison, Wisoconsin, we set-up bikes, load gear, discuss the week ahead, and then shuttle westward to arrive at Sinsinawa Mound Center, the mother house of the Sinsinawa Dominican Sisters, to embark on a self-guided tour of this historic place. Following the tour and a gourmet lunch, we depart for todays ride along quiet farm roands to meander between southwestern Wisconsin into northwestern Illinois to finally end the day in the delightful small town of Galena, Illinois.

Day 2: Galena South Loop
35 miles with up to 2,000 feet of climbing (80% paved/20% category 1 gravel)

The route this day is a mixed surface loop ride through the lush country side starting from Galena, then heading south to Hanover, and finally turning back north to pedal along the eastern shore of the Mississippi River. The final section of the route follows the Galena River via the Galena River Trail to return back to Galena and lunch at Depot Park. From the park we load up and shuttle a short distance across the Mississippi River to Dubuque, Iowa to visit the National Mississippi River Museum & Aquarium with exhibits exploring life in and around America’s riverways.

Following the museum, and if one were so inclined, it is a short 10 minute walk to our lodging at Hotel Julien which will help stretch the legs and keep you limber for the days ahead.

Day 3: Field of Dreams and Heritage Trail
42 miles with up to 1,500 feet of climbing (30% paved/70% category 1 gravel)

With a layover day in Dubuque, we start the day with a casual morning breakfast and then shuttle a short distance west to the small town of Epworth, Iowa to start our ride. Soon after departing Epworth, we visit the “Field of Dreams” Movie Site which was where the film of the same name was filmed in 1989. Here visitors can walk the iconic diamond nestled in the cornfields, tour the original farmhouse, and play catch with legendary Ghost Players.

Departing Field of Dreams, we jump onto the smooth gravel of the Heritage Trail, enjoy lunch along the way, and return back to Dubuque and to Hotel Julien. In the afternoon will be an optional stroll along the iconic Mississippi Riverwalk to take in the views of this mighty river.

Day 4: Upper Mississippi River
60 miles with up to 3,500 feet of climbing (90% paved/10% category 1 gravel)

This day offers the longest route of the tour thus far as we head north from Dubuque along the mighty Mississippi. The riding starts from O’Leary’s Lake Recreation Area which offers terrific views of the river along with the nearby dam and lock system. The riding weaves along the Mississippi with majestic views and then bobs back and forth into the adjacent lush farmland, all along narrow and quiet roads.

We take a break for another gourmet lunch at Riverside Park in the small town of Cassville, Wisconsin – founded in 1828 and initially speculated to become the capital city of the newly established Wisconsin Territory, but those plans fell through in the late 1830’s which abruptly ended the town’s growth. We continue north through the Upper Mississippi River National Wildlife and Fish Refuge to end at Wyalusing Beach where we shuttle a short distance to our lodging in Prairie du Chien, Wisconsin’s second-oldest city.

Day 5: The Driftless Ride
68 miles with up to 4,000 feet of climbing (80% paved/20% category 1 gravel)

We have finally arrived at the Queen’s Stage! The riding today will truly offer the best taste of the Driftless region as it undulates up and down 10% grades along the southern edge of the Wisconsin River Valley in terrain untouched by any glacial activity. The climbs are many, the surfaces are mixed, the views are spectacular, and the riding is driftless!

The final dozen or so miles offers a respite from the hills with a gentle ride in the Wisconsin River basin into the town of Spring Green, Wisconsin to end the day.

Day 6: Horribly Hilly and Blue Mound
42 miles with up to 3,500 feet of climbing (100% paved)

Spring Green, Wisconsin is home to Taliesin – the former estate of famed architect Frank Lloyd Wright – and soon after we depart on our ride for this final of the tour, we will make a stop at the Frank Lloyd Wright Visitor Center along the way.

Departing the visitor center, we head south into the area which holds the annual cycling event called the “Horribly Hilly Hundreds“. Some of our riding will be along the route for this event, but we guarantee that it will not be horribly hilly! Halfway through tooday’s route we stop at Blue Mound State Park and take in the views from one (or both?) of the Observation Towers. The final miles roll through the Driftless region where we end the riding near the town of Cross Plains and then shuttle back to Madison, Wisconsin to end the tour.

The Driftless Region Road Bike Tour: Logistics & FAQs

General Tour & Cancellation Policies

Please take a moment to familiarize yourself with all of our tour and cancellation policies, which can be found by clicking here.

Travel Insurance

If you have not already, now would be a great time to consider adding travel insurance to your tour. You are welcome to use any travel insurance company you would like. We recommend Generali/Trip Mate.

American Guests - use this link: http://www.generalitravelinsurance.com/get-a-quote.html?partner=LIZA0855

• The Premium Plan is the only plan which offers Pre-Existing coverage so long as the plan is purchased prior to Final Payment.
• The Premium Plan is the only plan that offers an optional Cancel For Any Reason - the policy must be purchased within 24 hours of initial trip deposit, the full trip cost must be insured, and if they cancel for Any Reason, it must be 48 hours prior to departure, and the reimbursement for an Any Reason claim is 60% of pre-paid, insured, non-refundable trip cost.
• Customer Service can be reached at 1-800-874-2442 for coverage questions and policy modifications or to purchase by phone. Agency Code: LIZA0855

Canadian Guests - use this link: https://tripmate.catravelins.ca/?utm_source=lizardhead