- REVIEWS
- QUESTIONS
Updating Results
Discover Madison, the home of Trek Travel—a vibrant college town, foodie hub, and the ultimate destination for self-guided bike tours.
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 »
Trip Wows
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
What Guests are Saying
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!
Read more
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!
Read more
Great Ride
Belleville Loop
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.
Dates & Pricing
Book early for the best price
-
Guaranteed
-
Join Waitlist
-
Private
-
Limited Availability
Itinerary
Day-to-Day
View full itineraryWhere to Arrive
Airport:
Dane County Regional Airport (MSN)
Pick-up location:
Mansion Hill Inn, Madison
Pick-up time:
11:00 AM
Where to Depart
Airport:
Dane County Regional Airport (MSN)
Drop-off location:
Mansion Hill Inn, Madison
Drop-off time:
11:00 AM
Additional Arrival Information
We recommend flying into Dane County Regional Airport (MSN) in Madison which is approximately six miles from your hotel. American, Delta, Frontier, Sun Country, and United Airlines serve MSN. From just outside the baggage claim, you can take a taxi to the meeting location. Taxi rides from the airport to your hotel will cost approximately $20.
Alternatively, you can fly into Milwaukee Mitchell International Airport (MKE). Milwaukee International Airport is an easy drive (85 miles) to the Mansion Hill Inn. Milwaukee Mitchell International Airport is a hub for most major rental car companies. You may also book a shuttle from MKE to Mansion Hill Inn with GO Riteway (1-800-236-5450). Please call for shuttle pricing and booking options.
Your Trek Travel host will meet you at Mansion Hill Inn (424 N Pinckney St, Madison, WI 53703) at 11:00 AM on the first day of the trip. Depending on the number of guests booked for your departure date, it is possible we will ask you to shift your meeting time by approximately 30 minutes. Please have your riding gear readily accessible to avoid having to unpack your luggage. After a trip overview, you may change into your cycling gear where you will then be fitted to your Trek bike ensuring you will be comfortable for the week. Following a safety talk and a review of the details of the route, saddle up to begin the day's ride.
If you will be late for the pick-up or are going to miss it altogether, please inform your Trek Travel host by calling 608-453-3685. If you cannot reach them, please call the Trek Travel Office (866-464-8735), and leave a message with your expected arrival time and contact details.
Additional Departure Information
Your Trek Travel host will meet you at 11:00 AM at the Mansion Hill Inn to collect your bike and equipment. You may check out up until 12:00 PM. From here you may choose to extend your stay in the area or secure your transportation back to the Dane County Regional Airport or Milwaukee. Do not book flights departing before 3:00 PM.
Cycle through the University of Wisconsin Madison’s Arboretum
Overview
Welcome to the cultural capital of Wisconsin! Madison is in a class by itself as it is home to the University of Wisconsin and the State Capitol, as well as being considered a cycling capital of the United States. Your host will meet you at the luxurious, Trek-owned Mansion Hill Inn for a bike fit and trip overview at 11:00 AM. You'll then head off cycling the Capital City State Trail along Lake Monona (adjacent to Mendota) as you head towards the city of Fitchburg.... Welcome to the cultural capital of Wisconsin! Madison is in a class by itself as it is home to the University of Wisconsin and the State Capitol, as well as being considered a cycling capital of the United States. Your host will meet you at the luxurious, Trek-owned Mansion Hill Inn for a bike fit and trip overview at 11:00 AM. You'll then head off cycling the Capital City State Trail along Lake Monona (adjacent to Mendota) as you head towards the city of Fitchburg. Take your time, enjoy the ride, and choose to grab a bite or drink at Great Dane Pub and Brewing Co. if the mood strikes. When you’re ready, you’ll return to downtown Madison through the University of Wisconsin Madison’s Arboretum, rich in greenery. (In the spring enjoy the Arboretum's stunning cherry blossoms!) Celebrate your first evening in Madison by selecting from our long list of excellent farm-to-table, locally sourced restaurant menus in town. Read More
Hotel
Mansion Hill Inn
Meals included
Ride Options
Ride Option 1
TODAY'S RIDE:
Madison to Fitchburg - Approximately 19 mi | 30 km and 794 ft | 242 m
Experience the Madison to Belleville Loop
Overview
Rise this morning to a delicious Mansion Hill Inn breakfast. This Victorian-inspired 10-room mansion was among the first homes in the city, and served as a primary residence of some of the city’s most notable citizens. Once you've fueled up, hop on your bike and head out to the charming town of Belleville. Today’s ride follows mostly flat, smooth roads with mild uphill climbs—just enough to get your heart pumping. Cruise along the rolling, rural roads that als... Rise this morning to a delicious Mansion Hill Inn breakfast. This Victorian-inspired 10-room mansion was among the first homes in the city, and served as a primary residence of some of the city’s most notable citizens. Once you've fueled up, hop on your bike and head out to the charming town of Belleville. Today’s ride follows mostly flat, smooth roads with mild uphill climbs—just enough to get your heart pumping. Cruise along the rolling, rural roads that also serve as the route for Ironman Wisconsin, as you experience quintessential Midwest scenery. On your way back towards Madison, stop in the artist’s enclave of Paoli, a popular meeting point for cyclists. Here you can grab a coffee and a snack from one of the eclectic cafes and visit the art galleries and antiques shops. Avid riders can continue on to the iconic, small Swiss town of New Glarus, with its chalets and European charm and the world-famous New Glarus Brewery, home to the one-and-only Spotted Cow farmhouse ale. Read More
Hotel
Mansion Hill Inn
Meals included
Breakfast
Ride Options
Ride Option 1
TODAY'S RIDE:
Madison to Belleville Loop - Approximately 50 mi | 80 km and 1,865 ft | 568 m
Ride Option 2
SHORT OPTION:
Madison to Paoli Loop - Approximately 31 mi | 50 km and 989 ft | 301 m
Ride Option 3
AVID OPTION:
Madison to New Glarus - Approximately 64 mi | 102 km and 2,345 ft | 714 m
Ride quiet country roads in the heart of Wisconsin
Overview
Enjoy another world-famous breakfast at the Mansion Hill Inn, but don’t delay too much as there’s plenty of adventure ahead! Start your morning cycling along the shore of Lake Mendota in preparation of a rolling ride through green pastures and verdant farmland. Enjoy the quiet country roads and plenty of ups and downs as you soak in this idyllic scenery at your own pace. This evening continue to experience the true taste of the Badger state and pop into Fromagin... Enjoy another world-famous breakfast at the Mansion Hill Inn, but don’t delay too much as there’s plenty of adventure ahead! Start your morning cycling along the shore of Lake Mendota in preparation of a rolling ride through green pastures and verdant farmland. Enjoy the quiet country roads and plenty of ups and downs as you soak in this idyllic scenery at your own pace. This evening continue to experience the true taste of the Badger state and pop into Fromagination, a hip Capitol Square cheesemonger where you can find many of the Midwest’s most heralded cheeses. Or, head to The Old Fashioned, a Wisconsin-themed restaurant offering elevated takes on the state’s regional offerings in a retro-style tavern. Try the cheese curds, double-brat burger to cap off your last night with a delicious twist on a local classic. Read More
Hotel
Mansion Hill Inn
Meals included
Breakfast
Ride Options
Ride Option 1
TODAY'S RIDE:
Madison to Indian Lake Loop - Approximately 46 mi | 74 km and 2,568 ft | 783 m
Ride Option 2
SHORT RIDE:
Madison to Missouri Tavern Loop - Approximately 32 mi | 51 km and 1,569 ft | 478 m
Ride Option 3
AVID RIDE:
Madison to Black Earth - Approximately 61 mi | 98 km and 3,293 ft | 1,003 m
Take a farewell spin along the Capital City State Trail
Overview
There's no better way to spend your last morning in Madison than with another spin along the Capital City State Trail. This short morning ride follows city bike trails out along Lake Monona. Following your ride, enjoy a satisfying Mansion Hill breakfast, pack your bags, and head to the airport for your next adventure or for your journey home.
Meals included
Breakfast
Ride Options
Ride Option 1
TODAY'S RIDE:
Madison to Monona Loop - Approximately 15 mi | 24 km and 459 ft | 140 m
View full itinerary to print.
View full itineraryActivity Information
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:
- Explore the many shops, galleries, and restaurants in downtown Madison
- Visit the Madison Museum of Contemporary Art
- Tour the Cedar Grove Cheese factory to taste a wide range of delicious cheese and learn about the cheese-making process firsthand from the experts
- Tour Frank Lloyd Wright's famous Taliesin Estate
- Explore Olbrich Botanical Gardens' 16-acre outdoor botanical garden and 10,000-square-foot conservatory
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.
- Ride With GPS app loaded with up to three daily route options
- Turn-by-turn directions and recommendations pinned on a map
- Emergency phone numbers and local highlights
Hotels
Madison, Wisconsin
Mansion Hill Inn
ExplorerEnjoy your stay at the Trek-owned Mansion Hill Inn. Renowned for its signature blend of intuitive hospitality and warmly sophisticated design, the property has a prime location off the Capitol square and steps from Lake Mendota. For 160 years, the Mansion Hill Inn has been host to travelers from around the world and is today a chance to experience a glimmer of that past. The 10-room boutique hotel also features decades of photography showcasing the Trek Bicycle heritage. Every room is at once luxurious and supremely comfortable, seamlessly blending timeless design with modern amenities. Please note all rooms have only one bed.
... Learn moreBikes & Gear
Ride the Best Bikes in the Industry
Road
E-Bike
Road
Trek Domane SL 7
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. It raises the bar to deliver incredible endurance road bike comfort without sacrificing performance and features highly responsive disc brakes, road-smoothing IsoSpeed technology, and electronic shifting. This new bike is lighter than ever before, and carbon wheels are standard on every Domane SL 7 bike.
Learn more
E-Bike
Trek Electric-Assist Verve+ Gen 3
Fun from the first pedal stroke, venture further on our Trek Verve+. With its low-step frame design, upright riding position, and the barely-there Bosch electric motor, the Verve+ has one goal: pure enjoyment. Designed for both comfort and adventure, get a boost up the hills when you need it with energy to spare.
Learn moreAdditional Gear
- Trek Travel water bottle to keep
- Universal phone case and mount along with portable battery backup
- RWGPS Experience App with pre-loaded routes and itinerary
- Bontrager front and rear Flare R lights
- A flat pack containing a tube, levers, and a CO2 cartridge with inflator
- Choice of Shimano SPD-SL road style pedals, Shimano SPD mountain style pedals, caged, or flat pedals
- Bontrager helmet
- Bontrager saddle
- For the most comfortable ride, we recommend you bring your own saddle. If you prefer, you can bring your own pedals and helmet on the trip and your host will install your gear on the first day during your bike fit.
Trip Inclusions
- Three nights of accommodation at a handpicked hotel
- Daily breakfast
- Daily lunch and dinner recommendations
- Trek Travel water bottle
- Up to three daily route options on riding days
- A bike lock, all necessary chargers and a floor pump
- Bike fit on the first day to help you find your optimal riding position, with recreational or avid set-up along with saddle preference
- Ride with GPS Experience on your phone for turn-by-turn directions and daily itinerary information. A universal phone case and portable battery will be provided for on-bike navigation
Additional Details
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:
- We do our best to avoid busy roadways as much as possible, however, urban riding and sections of busy roads are unavoidable for some segments of your rides.
Before and After Your Trip
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
Renowned for its signature blend of intuitive hospitality and warmly sophisticated design, the Trek-owned Mansion Hill Inn has a prime location off the Capitol square and steps from Lake Mendota. For 160 years, the Mansion Hill Inn has been host to travelers from around the world and is today a chance to experience a glimmer of that past. The 10-room luxury boutique hotel also features decades of photography showcasing the Trek Bicycle heritage. Every room is at once luxurious and supremely comfortable, seamlessly blending timeless design with modern amenities. 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:
Weather
Average monthly temperature and precipitation
| Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec | |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| High | 28.0°F· -2.2°C | 31.0°F· -0.6°C | 44.0°F· 6.7°C | 58.0°F· 14.4°C | 70.0°F· 21.1°C | 79.0°F· 26.1°C | 83.0°F· 28.3°C | 80.0°F· 26.7°C | 73.0°F· 22.8°C | 60.0°F· 15.6°C | 45.0°F· 7.2°C | 32.0°F· 0.0°C |
| Low | 12.0°F· -11.1°C | 15.0°F· -9.4°C | 25.0°F· -3.9°C | 36.0°F· 2.2°C | 47.0°F· 8.3°C | 57.0°F· 13.9°C | 61.0°F· 16.1°C | 59.0°F· 15.0°C | 50.0°F· 10.0°C | 39.0°F· 3.9°C | 29.0°F· -1.7°C | 18.0°F· -7.8°C |
| Rain | 0.67"· 1.70 cm | 0.69"· 1.75 cm | 1.04"· 2.64 cm | 2.13"· 5.41 cm | 1.97"· 5.00 cm | 2.14"· 5.44 cm | 1.91"· 4.85 cm | 1.74"· 4.42 cm | 1.35"· 3.43 cm | 1.15"· 2.92 cm | 1.07"· 2.72 cm | 0.84"· 2.13 cm |
FAQs
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, Discover, 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
