Introducing the cycling gem of the upper Midwest. Not only has Madison, Wisconsin been voted one of the “Best Places on Earth to Bike,” it is also home to Trek Travel and Trek Bicycle headquarters. Join us for a warm welcome into our hometown, and we’ll treat you like family. You’ll stay at the luxurious Mansion Hill Inn, a historic Trek-owned luxury property located a half-block from the Lake Mendota shoreline and just minutes from downtown. Madison, the college town to the University of Wisconsin, is not only ideal for cycling, it is also a hub for foodies with a wide selection of restaurants committed to local, farm-to-table menus. This is a self-guided trip with everything, from premium accommodations to great food and wine to, of course, outstanding cycling in the hills surrounding this cosmopolitan Midwest mecca. Learn more about Self-Guided trips and if they're right for you »
Enjoy fantastic routes through pastoral landscapes and views of Lake Mendota and Lake Monona
Experience Madison's unforgettable farm-to-table food scene—traditional cheese curds, brats, craft brews, and artisanal cheeses
Stay at The Mansion Hill Inn, Madison's most celebrated boutique hotel located in downtown Madison with luxurious accommodations and historic charm
Visit Olbrich Botanical Gardens, winner of the national Garden of Excellence Award, featuring 16 acres of outdoor specialty gardens
Explore the bike capital of the Midwest, boasting over 200 miles of biking (and hiking) trails
Beautiful rural landscapes surrounding Madison, Wisconsin
A very well-conceived trip with fun routes, excellent food, and interesting side tours. We felt Trek was fully behind us whilst enjoying the freedom of self-guidance. And the Trek bikes inspired confidence!
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We very much enjoyed our trip. We didn’t prepare at all and the bikes were a different style than we were used to. We very much enjoyed Madison, the Mansion Hill Inn and it’s staff, the restaurant recommendations, reading the Trek story, and the landscape around Wisconsin. Different length trip options were helpful to us and we chose the short options each time. We felt well supported by the Trek team during the trip. We celebrated our 60th birthdays by booking the trip and we are glad we did!
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Our self-guided bike tour was a once-in-a-lifetime experience that we intend to make a once-a-year experience!
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Great Ride
Experience first hand what makes Madison a platinum-rated cycling destination as you ride the bike trails through the city as well as endless quiet roads.
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Private
Limited Availability
There are a variety of non-riding options on this trip for riders who want to take the afternoon off or travel companions who want to spend little or no time in the saddle. Non-riders are welcome on a Self-Guided trip if they are staying in the same room with a riding guest. Non-riders will be offered a $500 discount from the trip price. Please contact a trip consultant for details and to book a non-riding companion. Some of these options may need to be scheduled before your trip—please contact one of our Trip Consultants for more information. Except as specified in the itinerary, expenses and transportation to these activities are not included in the trip price. Some non-riding options on this trip are:
On a self-guided tour you need to feel comfortable changing a flat, as this is a common event when cycling. All self-guided trips include Ride With GPS, an app which is like having a personal guide in your pocket! You'll get turn-by-turn directions and navigation along with local recommendations. In the rare case of a bicycle breakdown or mechanical issue beyond a simple repair, your Ride With GPS app will have your full itinerary with detailed contact information with emergency phone numbers to call for assistance. Learn more about our Self-Guided Bike Tours.
Stay at the Trek-owned Mansion Hill Inn, a historic 10-room hotel just steps from Madison’s Capitol Square and Lake Mendota. For more than 160 years, it has welcomed travelers from around the world with warm hospitality and thoughtful design. Each room features handcrafted furnishings, heated bathroom floors, and plush bedding, while framed photography throughout the inn celebrates Trek’s heritage. Please note, all rooms feature one bed.
Road
Experiencing your cycling vacation of a lifetime is not complete without a world-class bike and the Trek Domane SL 7 Gen 4 is the best on the road. Its carbon frame with road-smoothing IsoSpeed, responsive disc brakes, and Shimano Di2 electronic shifting deliver incredible comfort without sacrificing performance. Standard carbon wheels make this bike lighter and faster than ever.
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E-Bike
Fun from the first pedal stroke, the Trek Verve+ 3 helps you go farther with ease. Its low-step frame and upright riding position keep you comfortable, while the Bosch motor provides a natural boost up to 15 or 20 mph (region specific). Shimano hydraulic disc brakes deliver smooth, controlled stopping, so every hill and every mile feels relaxed and enjoyable.
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Your Day. You Decide.
Our self-guided vacations are designed to fit all types of travel styles. Whether you like to spend your time relaxing or on a non-stop adventure, you get to decide what your day looks like. Choose your mileage, itinerary, and experience level and leave the rest to us!
Your Trip Need to Knows:
Madison, WI
With plenty of outdoor activities and one of the strongest local food scenes in the country, this beautiful city is the perfect Midwestern retreat. Discover for yourself the largest producer-only farmers market in the U.S. or head to the Memorial Union for a local brew on the lakeside terrace. You will be enchanted by the cultural offerings and thriving nightlife that this university town brings to the forefront. We recommend the following accommodations for your pre- and post-trip hotel:
Where to Stay
Mansion Hill Inn
Stay at the Trek-owned Mansion Hill Inn, a historic 10-room hotel just steps from Madison’s Capitol Square and Lake Mendota. For more than 160 years, it has welcomed travelers from around the world with warm hospitality and thoughtful design. Each room features handcrafted furnishings, heated bathroom floors, and plush bedding, while framed photography throughout the inn celebrates Trek’s heritage. Please note: You will be staying here during your trip. www.mansionhillinn.com
The Edgewater
Nestled on the shores of Lake Mendota and walking distance to Capitol Square, The Edgewater is an urban resort steps away from Madison's vibrant downtown scene. Enjoy the hotel's many spa services and three on-site dining options. Grab a local brew from the hotel's waterfront pub or enjoy fine dining and regionally sourced cuisine at the Statehouse restaurant. www.theedgewater.com
Hotel Indigo Madison Downtown
Hotel Indigo Madison Downtown is walking distance from Madison’s downtown Capitol Square. Modern meets historic in the hotel’s interior with creatively crafted murals throughout the space that showcase the authentic style of the original architecture. The boutique hotel offers modern amenities in its fresh and funky guest rooms. www.ihg.com
Madison, WI
With plenty of outdoor activities and one of the strongest local food scenes in the country, this beautiful city is the perfect Midwestern retreat. Discover for yourself the largest producer-only farmers market in the U.S. or head to the Memorial Union for a local brew on the lakeside terrace. You will be enchanted by the cultural offerings and thriving nightlife that this university town brings to the forefront. We recommend the following accommodations for your post-trip hotel:
Madison, along with the rest of southern Wisconsin, is characterized by variable weather patterns and a large seasonal temperature variance. Late spring through to early fall bring the most ideal temperatures and conditions. High temperatures in summer average in the lower 80s (27-28ºC) but can reach 90ºF on average 12 days per year, often accompanied by high humidity levels. Please check the forecast in the days prior to your departure, always be prepared to dress in layers, and bring your rain gear, as rain is always a possibility in this region.
View our Packing List
To reserve your space on a trip, you can either call us at 866-464-8735 to speak with an expert Trip Consultant or book online any time by clicking the “BOOK THIS TRIP” icon near the upper right of each destination’s overview page.* Once you have submitted your reservation online, a Trip Consultant will contact you within one business day to answer any questions you may have and to confirm space, bike, and room availability on your desired trip. Your booking will be finalized once your no-risk deposit is paid. If you make a reservation more than 90 days prior to the trip, a $750 no risk deposit is due at the time of booking.** If you reserve your trip less than 90 days prior to the departure, the full balance is due at the time of booking. Once your booking is complete you will receive an email confirmation with important information pertaining to your trip.
*Please note that select trips cannot be booked online at this time. For those trips, please call a trip consultant at 866-464-8735.
**Deposit amounts vary for all Race, Cross Country, Special Edition, Ride Camp, and Self-Guided tours. Please confirm deposit amounts for all trips with your Trip Consultant at time of booking.
When a trip is booked, a guest confirmation letter is immediately sent out. One week prior to the trip start, you’ll receive an email containing your trip start meeting location reminder and any last-minute information that you’ll need to know before you go. Once you arrive at your destination, your Trek Travel host will brief you on the day-to-day plan for the trip and give you an overview on the daily route information and detailed maps within the Ride with GPS app. The turn-by-turn directions allow you to ride with complete confidence and independence.
We understand things happen in life and sometimes you have to cancel or change your tour.
Read our Cancellation Policy
Our Trip Consultants are available to assist and can answer your questions. Please call us at 866-464-8735.
Trek Travel recommends that you purchase a travel protection plan to help safeguard you and your travel investment against the unexpected. We offer a travel protection plan through Arch RoamRight that provides coverage for unforeseen events that could affect your ability to travel with us. Learn more about our Travel Protection
We've collaborated with a specialized travel agency committed to delivering tailored vacation planning, ensuring your entire Trek Travel journey is nothing short of unforgettable. Learn more about our Travel Services
Your Self-Guided trip price is per person based on two guests sharing a room. If you are a solo traveler or if you want to stay in your own private room while traveling with other people, you will have a Single Supplement Fee added to your trip price at the time of booking.
Didn't find what you were looking for? Check out our General FAQs section. You will find answers to the most common questions that don't necessarily pertain to a specific trip. See Self-Guided FAQs
Want to learn more about our trips? Watch our recorded Guide-Led Virtual Events—just visit our Trek Travel Youtube Channel and search for your trip.
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Our trips are guaranteed to run once we have one confirmed booking on the trip. Click here to view our full guarantee policy.
Trek Travel reserves the right to cancel trips with zero guests, therefore you must book with Trek Travel before making travel arrangements for the trip. We are not responsible for travel arrangements made prior to confirming your Trek Travel Trip. Select trips are not guaranteed.
This trip is currently sold out, but you may be added to the waitlist in the case of availability.
If a date is marked with Limited Availability, there are few spots left to book. We will secure additional rooms from our hotels before confirming your reservation.
Looking to travel with a small group? Ask our trip consultants about private trips and learn more.
If a date is marked as Private, it is reserved for a private group.
Don’t see exactly what you are looking for or looking for a custom date?
Call our trip consultants at 866-464-8735
Trek Travel offers three hotel levels to match your style. Luxury hotels provide elegant, thoughtful touches with exceptional hospitality. Explorer hotels blend modern amenities with local charm in unique settings. Comfort hotels are casual and conveniently located near Trek Travel activities.
Road: 1-3 hours of riding. Up to 25 mi (40 km). Up to 1,000 ft (300 m).
Gravel: 1-3 hours of riding. Up to 20 mi (35 km). Up to 1,000 ft (300 m).
Hiking: 1-3 hours of hiking. Up to 5 mi (8 km). Up to 1,000 ft (300 m).
Road: 2-4 hours of riding. 20-35 mi (35-60 km). Up to 2,500 ft (750 m).
Gravel: 2-4 hours of riding. 15-30 mi (25-45 km). Up to 2,000 ft (300 m).
Hiking: 2-4 hours of hiking. 4-8 mi (6-12 km). Up to 1,500 ft (450 m).
Road: 3-5 hours of riding. 25-55 mi (40-85 km). Up to 4,500 ft (1,500 m).
Gravel: 3-5 hours of riding. 20-40 mi (35-60 km). Up to 3,000 ft (900 m).
Hiking: 3-5 hours of hiking. 6-10 mi (9-16 km). Up to 2,000 ft (600 m).
Road: 4+ hours of riding. 40-70 mi (60-110 km). Up to 8,000 ft (2,400 m).
Gravel: 4+ hours of riding. 30-50 mi (45-80 km). Up to 4,000 ft (1,200 m).
Hiking: 4+ hours of hiking. 7-15 mi (11-24 km). Up to 4,000 ft (1,200 m).
Explore beautiful destinations with a curated blend of guided activities, local cuisine, handpicked accommodations, and itineraries to suit every traveler, from laid-back adventures to luxurious escapes.
Venture off the beaten path to unforgettable places, with fully-supported routes that combine gravel and paved roads in classic Trek Travel style.
Tackle an epic adventure that takes you point-to-point across mountains, countryside, and more.
See the pros in action at the biggest cycling events of the year.
Step into adventure with carefully designed routes, unparalleled hospitality, and deep-routed local connections.
Train like the pros in some of their favorite riding destinations.
Enjoy a bike tour on your schedule with just your chosen travel companions.
Sometimes it’s more convenient and comfortable to have your own room while on vacation. We understand and that’s why we offer a Single Occupancy option. The additional price guarantees a private room all to yourself
