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Bike Tour of Madison and Southeastern Wisconsin

A Six Day Cycling Tour of Wisconsin's Capital, Lake Geneva & Taliesin

Come see for yourself why this region is annually rated as one of the top ten bicycling destinations in the country!  We start and end in Madison, a city which effortlessly blends big city culture with small town charm.  Scenic lake views, miles of rolling terrain, a visit to Frank Lloyd Wright’s home Taliesin, and of course, the famous local Wisconsin brews and cheese cap off this Midwestern adventure to what is quickly becoming a foodie paradise!

This tour destination is available to private groups in 2020.  A great time to take this tour is the first or second week of June.  Contact us soon to start planning for your group.

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Best of Madison

Madison, Delafield & Lake Geneva, WI

Tour Difficulty

Rolling Hills and a few Short Climbs


6 Days, 5 Nights


Madison, WI

Nearest Airport

MSN Dane County Regional


From $2295 per person


6/2/19 - 6/7/19 6/9/19 - 6/14/19
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ItineraryDownload Itinerary

Day 1

23–42 miles, hilly

We meet in Madison, the heart of south central Wisconsin.  After bike fitting and a quick lunch, we’ll pedal miles of paved bike trails along lakes Mendota and Monona that border the heart of the city.  Stand up paddle boarders, sailors and kayakers dot the lakes as we pedal by. Popping out into the countryside, pastoral views of rolling farm fields dotted with Holsteins and iconic red barns provide views worth stopping for.  The afternoon’s spin ride is just the thing to warm us up for a great week of cycling in America’s Dairyland!

 We regroup at The Edgewater, our home for the next three nights.  Entirely remodeled in 2014, the hotel is situated in the heart of the city with views of both the resplendent Capitol Dome and the shores of Lake Mendota.  Enjoy your in room view of the first blush of sunset over the lake before dining as a group tonight at a local favorite steps from our hotel.

Day 2

31–68 miles, hilly

Next, we explore one of Wisconsin’s small town great escapes!  A pleasant morning ride transports us to New Glarus, established in 1845 by emigrants from Glarus, Switzerland.

Beautiful rolling hills, farms, wooded pastures and grazing cattle are much like the alpine meadows around Glarus, Switzerland.  Pedal through the quiet streets lined with chalets and Swiss museums and listen for the sound of yodeling and alphorns!  A short distance south of town is a chance to sample at your first authentic Wisconsin brew pub.  Savor the view on the beautiful terrace overlooking the town and surrounding countryside.  Venture into the charming town for lunch on your own in one of the many cafes before heading back to Madison via roads with ridge views of the distant city skyline.  Should you opt to shuttle back, the afternoon is yours to explore vibrant State Street, the pedestrian avenue which embodies the soul of the city, or a tour of the Capital with it's awe inspiring architecture and history.  Hundreds of shops, galleries and restaurants line this street that connects the University of Wisconsin campus to the Capital region of downtown.

Join us for a beverage of choice on the Edgewater’s new lakeside terrace before dinner on your own tonight.  Numerous farm-to-table options are within walking distance of the inn.

Day 3

44–53 miles, hilly

The work and inspiration from Wisconsin’s famous native son, Frank Lloyd Wright, can be seen throughout the cities and countryside of south central Wisconsin.  We begin our day after breakfast with a short shuttle to Frank Lloyd Wright’s personal home and studio, Taliesin.  A private guided tour awaits us of the Taliesin estate, truly one of the architecture world’s great treasures.  Even those not generally interested in architecture will be fascinated by the quirky and imaginative rooms that Wright built and lived in for 50 years.

We spin our way after our tour through the prairie edge of the Wisconsin River Valley to the natural beauty of the Wisconsin Heights. Craggy hills rise above the fertile valleys through which we bike.  We land early afternoon in the whimsical town of Mount Horeb. Norwegian heritage, artists, hipsters and farmers all can be found in this pleasant but decidedly urban feeling village.  We will pedal along the main drag known as “Trollway,” complete with a collection of carved Scandinavian wooden trolls - some gardening, some biking, some eating - but all welcoming us to the heart of the town.  Explore the streets dotted with specialty shops before dining on the delicious gourmet pizzas and great pub fare of The Grumpy Troll Brew Pub.  Should you wish, pop into the Fisher King Winery for a sip of Wisconsin’s local wines.

Spend the remainder of the afternoon in vibrant Madison before we gather as a group to savor yet another of Madison’s infinite number of fresh local foodie restaurants.

Day 4

40–73 miles, rolling hills

We reluctantly leave Madison behind today as we make our way east to land dotted with rolling ridgelines, open prairie, and small lakeside communities.  Glacial forces carved this gorgeous landscape, forming the gentle hills, sparkling lakes, and clear river streams that continue to captivate visitors.  We will stop for a catered lunch at Aztalan, one of Wisconsin’s most important archaeological sites.  Explore the grounds that were home to the ancient middle-mississippian culture that thrived here in 1000 A.D. before heading out on the bike to continue to our journey to Delafield.

Nestled along the shore of Lake Nagawicka in the Kettle Moraine hills, Delafield has a quiet charm all its own.  Its historic downtown is a pleasant blend of housing, specialty shops, award-winning restaurants, and day spas.  Historic sites include Hawks Inn, a colorful frontier stagecoach stop, and the campus of St. John’s Northwestern Military Academy, the oldest military academy in Wisconsin.  Our home for the night is the Delafield Hotel steps away from the charming business district.  Unwind with a massage or treatment at the on-site spa before dining on your own this evening at one of the many downtown options.

Day 5

42–56 miles, rolling hills with a few steep hills

Between Delafield and Lake Geneva lies the southern end of the Kettle Moraine, the landscape shaped by the glaciers that covered the region thousands of years ago.  Forests and bogs rise from the prairie and welcome us along our route to charming Lake Geneva.  Lunch is on your own today in one of the numerous options in this vibrant lakeshore resort town.

Historically, Lake Geneva has been a summertime playground for Chicago’s wealthiest families, which can be seen in the grand palatial homes that surround the beautiful lake.  The lake itself is spring-fed, which accounts for the crisp, clean, clear water.

Opt to explore some of the boutique shops, pedal along the scenic lakeshore to catch a glimpse of the beautiful homes, try your hand at stand up paddle boarding, or simply relax in your lakefront room savoring the peaceful water view from at The Geneva Inn, our home just outside the bustling town.

Join us for happy hour on the lake before dining as a group on the lovely cuisine of the Geneva Inn.

Day 6

32–46 miles, rolling hills

Our final day begins with one last breakfast on the shores of Lake Geneva before a short shuttle to the northwest.  Our final ride spins toward Madison on empty backroads seemingly created for road cycling enthusiasts!  Rolling wooded terrain interspersed with ridgetop views of the surrounding open pastureland dotted with cows provides perfect views of quintessential Wisconsin.  One last trip on the vast network of Madison’s paved bike paths takes us the final stretch home.  Lunch and showers await before departure.


$2,295 - $2,395
Bike Rental
Single Room Supplement

Low end of tour price range reflects the 6 month Early Bird Discount.  High end of price range reflects no Early Bird Discount. 

What's Included in Your Tour Price


5 nights at boutique inns


Dinner on Nights 1, 3, & 5 All lunches except 1; All breakfasts; snacks; and hors d'oeuvres most nights.

Services of Expert Guides

Carolina Tailwinds maintains a guest to guide maximum ratio of 7:1 on all our tours.  Guides are ready to show you the hidden wonders of each and every destination.

Full Route Support & Luggage Transfer

Service of 1 – 2 support vans on route every day.

Complimentary Airport Transportation from Madison

Carolina Tailwinds picks up on the morning of Day 1 and drops off in the late afternoon on Day 6 at the Madison, WI airport (MSN) to and from our tour start at the Sheraton in Madison, WI.  Timing formally coordinated 2 weeks prior to tour date.

More details on what's included: 

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Nights 1, 2 & 3

The Edgewater

Located on the shores of Lake Mendota, The Edgewater is just down the street from the Capitol Square, the heart of downtown Madison.  It's within walking distance of State Street and its eclectic restaurants and shops.  The hotel offers over 200 guest rooms, an outdoor plaza and pier, several restaurants and lounges, a luxurious spa, and extraordinary facilities for meetings, events, and weddings.

The Delafield Hotel

Night 4

The Delafield Hotel

With sophisticated elegance and classic old-world charm, The Delafield Hotel is a sought-after, full service boutique hotel just outside of the Milwaukee area.  Is is one of only ten properties recognized as Four Diamond in the state of Wisconsin and the specialty shops and stores of quaint downtown Delafield are just steps away from the hotel front doors.

Night 5

The Geneva Inn

Located on the scenic shores of Geneva Lake, The Geneva Inn is home to panoramic lake side views from our hotel and restaurant.  With charming accommodations, attentive staff and award winning cuisine, The Geneva Inn is one of the most sought after year round retreats in Lake Geneva, Wisconsin.



The terrain is a combination of gently rolling terrain, hills, and, in a few spots, challenging climbs.  As with all Carolina Tailwinds tours, less ambitious cyclists can take advantage of short cuts and strategic "leap frog" van shuttles along the route to tailor the route to their needs.

Tour Point of Origin:

Comfort Inn, 722 John Nolen Dr, Madison, WI  (608) 255-7400

Getting to the Tour Start (Madison, WI):

Driving:  Driving distance to Madison, WI from:

  • Chicago: 143 miles
  • Minneapolis: 268 miles
  • Cincinnati: 444 miles
  • Nashville:  622 miles
  • Washington: 853 miles
  • Charlotte: 905 miles


Dane County Regional Airport (MSN)
Service by Delta, United, American Eagle, & Frontier Airlines with 11 non-stop destinations to airline hubs.

6 miles from tour start/end location in downtown Madison.

Most airlines recommend that you arrive at the airport 1 1/2 to 2 hours before your flight's scheduled departure time.

Ground Transportation:  Taxis and rental cars are available at the airport.  

A complimentary Carolina Tailwinds shuttle will be available to and from the airport at a designated time before and after the tour.

Parking:  We have arranged for long term parking there for the duration of your tour.  We will end the tour at the same inn with an opportunity to shower there prior to departure.

Arrival & Departure Timing:

Arrive at the tour start location no later than  12:00 p.m. on Day 1 (11:00 a.m. if renting a bicycle.)  Arrive a day or more early to enjoy all that Madison offers on your own.  We will return to Madison on Day 6 by 2 p.m.

Extend Your Stay:

Madison  is a vibrant, effortlessly cool town that is full of fun things to see and do:

Olbrich Botanial Gardens & Bolz Conservatory:  Olbrich Botanical Gardens, winner of the national Garden of Excellence Award, features 16 acres of outdoor specialty gardens, including a sunken garden with an eighty-foot reflecting pool and a perennial garden with a meandering stream. A two-acre rose garden with a two-story, stone rose tower highlights Midwest-hardy shrub roses. The exotic Thai Pavilion and Garden is the only one in the continental U.S. The year-round tropical Bolz Conservatory, a sunny 50-foot-high glass pyramid, houses ferns, palms, and flowering plants along with a waterfall, birds, and fish.

Madison Museum of Contemporary Art:  Changing exhibits and collections of contemporary and modern art. Exhibitions are free and open to the public. The museum's permanent collection includes nearly 5,000 works of art, with a solid core of American prints, photographs and drawings. The collection also encompasses paintings, sculptures, and other works by some of the most innovative artists of our time.

Wisconsin State Capitol:  Rising between the picturesque waters of Lake Monona and Lake Mendota, the magnificent granite structure of Wisconsin's Capitol glows like a beacon, accenting the Madison skyline. The best way to experience the beauty of the Capitol is to see it yourself. Free tours are offered daily, year-round except for select holidays.

Overture Center for the Arts:  Overture Center for the Arts is a stunning architectural landmark in the heart of Madison’s thriving cultural arts district. In addition to housing ten resident organizations and presenting more than 200 performances, art exhibitions, and educational and community events each year, Overture offers a variety of venues for performances, corporate meetings, conventions, trade shows, weddings, banquets, and receptions.

State Street:  Lined with restaurants, charming boutiques and specialty shops, the real heart of downtown Madison can be found on State Street. During the summer, State Street comes to life with musicians, dancers, and outdoor patio dining. Spanning seven blocks, State Street has something to interest everyone–from art galleries and coffee shops to bookstores and pubs. Take in the best Madison has to offer by relaxing on a warm summer evening with a beer on a warm summer evening on State Street.

Monona Terrace:  Designed by Frank Lloyd Wright himself, the Monona Terrace is often an unseen treasure just steps away from the State Capitol building. Featuring rooftop dining, the popular Lake Vista Café overlooks both Lake Monona and downtown Madison’s cityscape. The café offers fresh seasonal specialty foods in addition to menu offerings like Tandoori Chicken Skewers and tossed salads, making this Café an ideal place to enjoy a meal. Additionally, Monona Terrace is home to the William T. Evjue Rooftop Garden. This rooftop garden features exquisite trees, plants and foliage with wonderful views of the city, securing Monona Terraces' spot as a top summer destination in Madison.

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