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The Suite Life

Madison’s most celebrated boutique hotel, The Mansion Hill Inn is renowned for its signature blend of intuitive service and warmly sophisticated design. For 160 years, the Mansion Hill Inn has been host to travelers from around the world and is today a chance to experience a glimmering time past. Discover our favorite Midwestern retreat when you join us for your personalized Project One experience.
Stay at an urban retreat, Madison's Mansion Hill Inn, on your Trek Factory Experience

In 1857, Alexander A. McDonnell bought a small wood lot on one of the most prominent hills in Madison. The town was nearly twenty years old by that point, and the fledgling state of Wisconsin was experiencing such a boom that the old Capitol building had been outgrown. McDonnell was the contractor for a new Capitol building and the lot he selected on what was known as Big Bug Hill was a short walk from the construction site. McDonnell hired the architect August Kutzboch, a German émigré who was renowned as one of the premier architects in Madison along with his partner Samuel Donnell. Together the two men built what McDonnell termed “the best house money could buy.”

The German Romanesque Revival building, considered by some to be the finest of its type in the country, includes wrought iron from the balconies to buttresses and arched windows. Inside the 9,000 square foot Madison hotel is a four-story, oval-shaped mahogany spiral staircase leading to a belvedere. Light passes into the marble foyer through etched Venetian glass windows. Originally, there were oil-painted wall designs.

The hotel’s days as a single-family residence ended at the turn-of-the-century. It then became a fashionable boarding house run by Carrie Pierce, where some of Madison’s most notable citizens lived. In the 1930’s, well after boarding houses fell out of favor, the building was converted into apartments, a condition that persisted until 1983, when the Alexander Company purchased the Inn, transforming it into a boutique hotel.
Stay at the Mansion Hill Inn on your personalized Trek Factory Experience
For over twenty years, the Mansion Hill Inn lived up to the ideals set forth by all those whom invested so much time, effort, and money into this house. In March 2008, the Mansion Hill Inn was purchased by Trek Bicycle and Trek Hospitality. At that point, Trek embarked on an extensive renovation project that sought to update the hotel’s amenities and preserve the home’s history. Each of the ten charming rooms has been restored, highlighting the property’s historical charm. Trek sought to expand the amenities available by preserving the hotel’s classic parlor and creating a majestic bar for entertaining. The house has been furnished with elegant pieces and state of the art fixtures. Additionally, Trek restored the belvedere at the top of the stairs and some of the ornate wrought-iron on the balconies and front porch among other pieces.

From its origins as a small woodlot on Big Bug Hill to Madison’s finest hotel on Mansion Hill, the sandstone home at 424 North Pinckney Street has emerged as a landmark in both the hospitality industry and the history of the city of Madison. The elegance, beauty, and history of the home undoubtedly will continue to impress visitors for many years to come.
Stay at the Mansion Hill Inn on your personalized Trek Factory Experience

Experience the Mansion Hill Inn on your Trek Factory Experience»

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Looking to travel with a small group or looking for a custom date?
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What is the Difference?

Ultimate Luxury:

Savor some of the most spectacular, 5-star properties in the world. Exuding luxury and elegance, these one-of-a-kind accommodations offer the chance to rejuvenate at award-winning spas, dine at Michelin-starred restaurants, and more.


Enjoy luxurious accommodations handpicked for a refined experience. From signature spa treatments to delicious local cuisine, you’ll be more than provided for; you’ll be pampered.


These handpicked hotels provide relaxation and fun in a casual and comfortable environment. Delicious cuisine and great service mix perfectly for a memorable stay.


On select cycling vacations, you’ll stay at a mix of Explorer and Luxury hotels. Rest assured, no matter which hotel level you’re at, our trip designers carefully select every accommodation.

Activity Level

Level 1:

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).

Level 2:

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).

Level 3:

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).

Level 4:

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).

What are your trip styles?

Classic - Reserve:

Savor the finer things as you relax in luxurious 5-star accommodations and wine, dine, and ride in some of the most unforgettable destinations around the world.

Classic - Signature:

Explore beautiful destinations by bike, enjoy extra inclusions, savor delicious local cuisine, and enjoy the perfect mix of accommodations.

Classic - Discover:

Enjoy a casual cycling vacation with fantastic routes and comfortable accommodations.

Ride Camp:

Train like the pros in some of their favorite riding destinations.

Pro Race:

See the pros in action at the biggest cycling events of the year.

Cross Country:

Tackle an epic adventure that takes you point-to-point across mountains, countryside, and more.


Enjoy a bike tour on your schedule with just your chosen travel companions.

Single Occupancy

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