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Wisconsin farmland on Madison Self Guided Bike Tour
Madison, Wisconsin state Capitol building
Two cyclists in the farmlands of Wisconsin
Mansion Hill Inn on Madison Self-guided bike tour
Wisconsin dairy cows on a Madison Self Guided Bike Tour
Ride the roads of Wisconsin on our Madison Long Weekend bike tour
Experience Madison Self Guided Bike Tour
Rolling hills near Madison, WI
Wisconsin farmland on Madison Self Guided Bike Tour Madison, Wisconsin state Capitol building Two cyclists in the farmlands of Wisconsin Mansion Hill Inn on Madison Self-guided bike tour Wisconsin dairy cows on a Madison Self Guided Bike Tour Ride the roads of Wisconsin on our Madison Long Weekend bike tour Experience Madison Self Guided Bike Tour Rolling hills near Madison, WI

Madison Self-Guided Bike Tour

Cycle the Lakes and Countryside of Wisconsin

Let us introduce you to 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. Book your trip with confidence »
Learn if a self-guided trip is right for you »
Madison area countryside and barn
From:
$1799 Per Person
Duration:
4 Days & 3 Nights
Rider Level: ?
3 - Active Non-riders Welcome
Trip Style: ?
Self-Guided
Hotel Level: ?
Explorer
Reviews:
From $1799 per person View All Details
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
Cyclist in countryside near Madison
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!
-John, Trek Travel Guest

Dates & Prices

The Earlier You Book, The Greater The Rewards

We reward our guests with lower pricing and more dates to choose from the earlier you book. Rest assured, once you book, your price and date are guaranteed.
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Sold Out/
Waitlist
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Single Occupancy from: +$500
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Jul 18 – Jul 21 
$1799 / Person, Double Occupancy Book this date
Aug 1 – Aug 4 
$1799 / Person, Double Occupancy Book this date
Aug 8 – Aug 11 
$1799 / Person, Double Occupancy Book this date
Aug 29 – Sep 1 
$1799 / Person, Double Occupancy Book this date
Don't see your ideal travel date? 
Call us at (866) 464-8735 for custom date availability
Looking for a one of a kind, once in a lifetime experience?
Look no further. Choose your trip date, get your group together and we will do the rest. Private trip pricing is as follows:

  • 10+ Guests Price as advertised*
  • 8-9 Guests +$750 per person to trip price*
  • 6-7 Guests +$1,500 per person to trip price*
  • 4-5 Guests +$2,000 per person to trip price*
  • 2-3 Guests +$3,000 per person to trip price*
  • 1 Guest        Call us for pricing*


Traveling with a small group? Consider semi-private trips.
For groups of up to six people, semi-private trips offer unique flexibility within a larger Trek Travel guided trip. Learn more »

*Pricing, availability and guest minimums are all subject to change at any time. Certain dates have a minimum number of guests required, please contact us for details. Private pricing is not available on Ride Camp, Race, Special Edition or Cross Country style trips.
Looking for a date that you don’t see?
Look no further. Simply tell us your preferred travel dates and we’ll work together to deliver the same great trip on your custom schedule.
*Pricing, availability and guest minimums are all subject to change at any time. Certain dates have a minimum number of guests required, please contact us for details. Custom dates are not available on Ride Camp, Race, Special Edition or Cross Country style trips.
Want to customize this trip?
We've got you covered. We’ll work with you to build your perfect vacation from scratch, including your choice of riding, accommodations and dining options. With the help of our trip designers and travel experts, the world is available like never before.
*Pricing, availability and guest minimums are all subject to change at any time. Certain dates have a minimum number of guests required, please contact us for details. Custom trips are not available on Ride Camp, Race, Special Edition or Cross Country style trips.

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.

Today's Ride:

Madison to Fitchburg Loop
Approximately 20 mi | 31 km and 794 ft | 242 m

Hotel:

Mansion Hill Inn

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.

Today's Ride:

Madison to Belleville Loop
Approximately 50 mi | 51km and 1846 ft | 296 m

Short Option:

Madison to Paoli
Approximately 21 mi | 24 and 970 ft | 284 m

Avid Option:

Madison to New Glarus Loop
Approximately 64 mi | 82 km and 970 ft | 563 m

Hotel:

Mansion Hill Inn

Included Meals:

Breakfast

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.

Today's Ride:

Madison to Black Earth Loop
Approximately 60 mi | 98 km and 3,293 ft | 1,004 m

Short Option:

Madison to Cross Plains Loop
Approximately 52 mi | 84 km and 2812 ft | 857 m

Hotel:

Mansion Hill Inn

Included Meals:

Breakfast

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 past Lake Waubesa and through the Waubesa Wetlands State, one of the highest quality and most diverse wetlands remaining in southern Wisconsin. 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.

Today's Ride:

Madison to McFarland Loop
Approximately 30 mi | 49 km and 831 ft | 253 m

Included Meals:

Breakfast

Hotels

hotel image

Mansion Hill Inn

Madison, Wisconsin

Explorer Accommodation | Enjoy 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 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.

What's Included

For us, the details matter most

Every moment of a Trek Travel self-guided bike trip has more than you could have ever dreamed. More experiences. More scenery. More choice. It's the little additions to every Trek Travel cycling vacation that make it truly special. And that's how we help you create more memories.

bike

Trek Emonda SL 5 Disc

The Trek Emonda SL 5 Disc is the perfect bike for your self-guided trip. Its lightweight aerodynamic frame will have you cruising with ease throughout your day. The Shimano hydraulic brakes give you consistent stopping power and control in any weather. The Emonda SL 5 is equipped with Shimano 105 components, the workhorse group of Shimano's lineup that will keep your focus on enjoying the hills with its buttery smooth shifting. We think you'll like this bike so much, you'll want to get one of your own! Learn More

bike

Trek Electric Assist Verve+ 3

With its Low-Step frame design, hopping on and off the Trek Verve+ 3 is super easy. The front suspension will take the edge off any bumps in the road and the Bosch system will keep you smiling from ear to ear. The integrated battery keeps this bike looking sleek as you pedal through amazing terrain. Learn More

WHAT'S INCLUDED

  • Three nights of accommodation at a handpicked hotel
  • Daily breakfast
  • Daily lunch and dinner recommendations
  • Trek Emonda SL 5 disc road bike or Trek Electric-Assist Verve+3 Lowstep
  • Up to three daily route options on riding days
  • Trek Travel water bottles to keep
  • Each bike is equipped with a Garmin GPS computer, a flat pack containing one tube, two tire levers, CO2 cartridge with inflator, and a patch kit (the flat pack is only large enough for these items so if additional gear is needed, please plan to bring your own bar bag or small backpack for daily rides)
  • A mini frame pump, front and rear lights
  • Bontrager helmet (optional if you do not bring your own)
  • Bontrager saddle (we suggest you bring your own for the most comfortable fit)
  • Shimano clipless pedals or flat pedals (optional if you do not bring your own)
  • 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 to get all the information you need on your self-guided adventure

GEAR

  • Trek Emonda SL 5 disc road bike with Shimano Di2 electronic shifting or Trek Electric-Assist Verve+3 Lowstep, available in a limited quantity
  • Garmin GPS computer with mount
  • Trek Travel water bottles to keep
  • Shimano clipless road pedals, Shimano clipless mountain pedals, or flat pedals (optional if you do not bring your own)
  • Bontrager helmet (optional if you do not bring your own)
  • Bontrager men's and women's specific saddles
  • Bontrager front and rear Flare R lights
  • Each bike is equipped with a flat pack containing one tube, two tire levers, CO2 cartridge with inflator, and a patch kit (the flat pack is only large enough for these items so if additional gear is needed, please plan to bring your own bar bag or small backpack for daily rides)
  • A mini frame pump
  • A bike lock, all necessary chargers, and a floor pump
  • Coupon valued up to $500 off a new Trek Bicycle. Your coupon will be delivered via email prior to your trip.
  • For the most comfortable ride, you may choose to bring your own pedals, saddle, and helmet on the trip. Your Trek Travel host will install your gear on the first day during your bike fit.

WHAT'S NOT INCLUDED

For self-guided trips you are welcome to thank your host with a gratuity based on your level of service.
  • Airfare and transportation to and from the trip meeting/departing locations
  • Lodging before and after the trip
  • Personal items purchased during the trip
  • Optional activities not scheduled by Trek Travel
  • While we provide daily breakfast, the other meals are not included. On self-guided trips, Trek Travel provides restaurant recommendations and invites you to explore the local cuisine at your leisure.

More Information

Rider Level: 3 - Active?

AVERAGE DAILY MILEAGE:
57 kilometers / 36 miles
TOTAL MILES:
286 kilometers / 178 miles
AVERAGE DAILY ELEVATION:
961 meters / 3,154 feet
TOTAL ELEVATION:
4,806 meters / 15,770 feet
TERRAIN: UNDULATING
Wisconsin's many miles of trails and varied terrain make it an ideal place for bicycling. Wisconsin consistently ranks as one of America's best places to bike. Rides over the course of your trip will range from urban bike trails to journeys out across quiet southern Wisconsin farm roads. Madison is fairly flat in nature whereas some of the terrain outside of the city is rolling. Short mellow climbs and descents are characteristic of the riding landscape in this part of the state. See day by day itinerary for specific daily ride distance and elevation options.
NON-RIDING ACTIVITIES:
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. 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's 16-acre outdoor botanical garden and 10,000-square-foot conservatory

See itinerary for specific daily ride distances and elevation options. On all of our vacations, Trek Travel seeks to find quiet, paved secondary roads or bike paths to experience a region; busy roads are avoided as much as possible. Our itineraries are an approximation of our trips. Trek Travel strives to offer every guest a vacation of a lifetime on every trip. At times routes, hotels, activities, etc. listed here may change at the discretion of the trip designer or Trek Travel's local experts to improve the trip experience.

Averages and totals are calculated from our "Today’s Ride" options.

Travel Details

How to Get There

FLY INTO:
Dane County Regional Airport (MSN)
MEETING TIME:
11:00 AM
MEETING LOCATION:
Mansion Hill Inn, Madison

Say Farewell

FLY OUT OF:
Dane County Regional Airport (MSN)
DEPARTING TIME:
11:00 PM
DEPARTING LOCATION:
Mansion Hill Inn, Madison

Arriving

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. Here you will be fitted to your Trek bike ensuring you will be comfortable for the week. After a safety talk and reviewing the details of the routes, 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 host. You will receive an email a week before the trip start with their names and contact details. If you cannot reach them, please call Trek Bicycle Madison West (608-833-8735), and leave a message with your expected arrival time and contact details.

View our pre hotel recommendations

Leaving

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.

View our post hotel recommendations

Planning For Your Trip

Packing and Weather

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 but can reach 90 Farenheit 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. Packing List

Before and After Your Trip

before

Before & After: 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:

Customer Reviews

Why Trek Travel

Our Bikes

Our unrivaled selection of Trek Bikes sets the bar for quality and comfort. From the ultra-smooth Trek Domane SL 7 to the Trek Electric-Assist Verve+, you deserve the best ride on your vacation. Plus, we offer a range upgrade options to take you the extra mile.

Our Guides

Our guides are trained to make your trip magical. They aren't just experts in riding; they're trained in delivering uncompromising service in ways you won't believe. We know that it's the unexpected surprises that make a trip magical. That's why our guides pride themselves on anticipating your needs before you ask.

Your Day. You Decide.

Our vacations are built to deliver the ultimate in flexibility, from extreme relaxers to hard-core roadies. You pick your mileage, itinerary and experiences. We take care of the rest.

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