Private Tours

Bascom Hill tour

Learning Matters

Climb the hill to see Old Abe, good luck symbol to generations of UW students. The UW campus is packed with history and architecture galore, from stately brick and sandstone buildings of the 1850s to “the worst building in the history of American universities.” This tour requires strenuous walking uphill.

Length: Approximately 1 1/2 hours

Isthmus Bike Tour

Cycle the East-side

Covering Madison’s near east neighborhoods, highlights of this this two-wheeled tour include revitalized industrial buildings and a Native American effigy mound.

Length: Approximately 2 hours

GREENBUSH NEIGHBORHOOD

Spaghetti Joints, Synagogues and Urban Renewal

Mainstream Madison thought of the historic Greenbush neighborhood as spaghetti restaurants, Prohibition speakeasies and organized crime in a blighted neighborhood. Residents of the neighborhood, on the other hand, remember it as a warm home where neighbors looked out for neighbors, be they German, Italian, or Russian Jewish immigrants, or African Americans who came in the Great American Migration.  Urban renewal efforts in the 1960s tore the heart out of the neighborhood, but many traces remain, and the descendants of the original residents keep memories alive.

Length: Approximately 2 hours

King Street tour

Where Madison First Happened

Over the years, Madison’s very first street has been home to its first fast-food lunchroom, first high-volume grocery, and Madison’s first teacher. Throw in the Majestic (Madison’s oldest continually operating theater), an Art Deco high-rise, and a Turkish bath; and you’ll realize there’s a lot about this well-visited street you may not know.

Length: Approximately 1 hour

Machinery Row Tour

Threshers, Tractors, Trains & Traveling Salesmen

During the booming 19th century, the east side of Madison was the center of the agricultural implement manufacturing industry in Wisconsin. Railroads converged here and the area became “Machinery Row.” Learn about this history and see factories, commercial buildings, a railroad station, hotels, and a candy company to boot!

Length: Approximately 1½ hours

Mansion Hill east tour

Lifestyles of the Rich and (Once) Famous

Big Bug Hill, Aristocracy Hill, Mansion Hill. Travel through time with us to see the stately sandstone mansions built by Madison’s early elite, including the Old Governor’s Mansion, home to 17 Wisconsin governors. Times change, residents change, but these elegant buildings continue to inspire.

Length: Approximately 1 ¼ hours

Mansion hill west tour

Meet Movers & Shakers

Hidden among the student rentals, you’ll see where Madison’s “big bugs” settled. Time-travel with us from the 1850s to the 1940s to discover a variety of architectural styles and hear stories about the people who built our city—the Jackson, Tenney, Quisling, Mautz, Steensland, and Stevens families.

Length: Approximately 1¼ hours

Maple Bluff Cambridge rd tour

Lakeside Architectural Gems

Explore Cambridge Road’s rich variety of architecture including Prairie, Shingle, Mediterranean Revival, and French Norman Revival styles. Learn about the lives of civic and business leaders who resided here and about the prominent architects who designed these homes. The Village of Maple Bluff never became part of Madison—discover why!

Length: Approximately 1¼ hours

Marquette Bungalows tour

What’s a Jerkinhead?

In just two city blocks, you’ll learn about these unique Craftsman-style bungalows that are modest yet so appealing. (And you’ll be able to identify a jerkinhead!) They weren’t designed by trained architects, but by craftsmen working for the Karrels Building Company between 1924 and 1929.

Length: Approximately 1 hour

Nakoma tour

Sundry Architecture in an Early Suburb

Take a trip with us down historic Nakoma Road and learn about one of Madison’s first suburbs and the prominent residents and architects responsible for its development. View fine homes on lush lots as well as one of Madison’s oldest buildings, the Old Spring Tavern.

Length: Approximately 1 1/2 hours

Old Market Place

Divergence by the Lakeshore

A tour of this near east-side neighborhood between East Washington and the shore of Lake Mendota will demonstrate how a historic factory, water utility building and school have been adaptively repurposed into apartments.  See both Madison’s earliest African American neighborhood and lakeside homes of the well-to-do.

Length: Approximately 1 ½ hours

Orton Park tour

Distinctive Architecture & Stately Oaks

Now a place of relaxation, recreation, and celebration; Orton Park once served as a final resting place for the dearly departed. Tour one of Madison’s oldest neighborhoods and see homes designed by local architects in distinctive styles as diverse as Italianate, Queen Anne, Greek and Tudor revival, Craftsman, and Prairie.

Length: Approximately 1¼ hours

Prospect and Castle Place

Progressive Era Treasures

Early 20th century, well-to-do Madisonians built comfortable homes along the Lake Mendota shore, many of them designed by preeminent Madison architects Claude and Starck. The designs of these homes encompassed the styles popular in that era: Tudor and Georgian Revival, Craftsman, Prairie and Colonial Revival. Walk with us through this delightful neighborhood as we learn how eminent people lived a century ago and discover more about the architecture and history of this eerie remnant of Madison's earliest years.

Length: Approximately 1 ½ hours

State Street tour

That Great Street

The artery connecting the State Capitol to the UW campus lies at the beating heart of our city.  So many people, stories, and fascinating structures—it’s hard to fit them into one tour. Overture Center, the Orpheum, Peace Park, flatiron buildings! Come walk with us and feel the excitement.

Length: Approximately 1 ¼ hours

*This tour is not available as a private tour in 2024

Sunset Hills tour

Mad Mid Mod

These 1950s single-family houses will remind you of cigarettes and cocktails. Platted in 1953, this subdivision of 94 homes on Madison’s west side established deed restrictions that required architect-designed “Modern” homes of high style and high quality. Attached garages only!

Length: Approximately 1 hour

Third Lake Ridge West tour

Brewers & Burghers

Wild and woolly Willy Street started as a haven for 19th-century German immigrants. They made their homes, taverns, shops and churches in the unique buildings on Williamson and Jenifer Streets. Learn how this area grew through the decades to become one of Madison’s most distinctive neighborhoods.

Length: Approximately 1 ¼ hours

University Heights tour

Iconic Architects

Frank Lloyd Wright, Louis Sullivan, Frank Riley, Claude & Starck, Alvan Small—oh my! This distinguished campus-adjacent neighborhood has been home to some of Madison’s most prominent university faculty. As you explore the area, guess (or ask!) what many of the street names have in common.

Length: Approximately 1¼ hours

*This tour is not available as a private tour in 2024

UW Ag Campus tour

Birthplace of the Wisconsin Idea

Moo-ve through the historic agricultural campus and learn about the scientific discoveries made within these 19th-century buildings of varied architectural styles. It’s so much more than cows (although you may see some of those too!).

Length: Approximately 1½ hours

Vilas Tour

Experienced how the historically unique Vilas Neighborhood has it all, from Indian Mounds and the popular Vilas Park to architecture ranging from Prairie and Queen Anne, to Tudor and Georgian Revival. Rising up a hill from wetlands and Lake Wingra, the Vilas Neighborhood (originally called Wingra Park) developed as one of Madison’s first residential suburbs as the city expanded. Learn what was destroyed and what was preserved as new homes went up. Over 130 years later, the neighborhood retains its unique aspects and continues to bustle with liveliness.

Length: Approximately 1 1/2 hours

Westmorland tour

From Farmland to Frank Lloyd Wright

No repetitious development of cookie-cutter houses in this pioneering west-side suburb. Find the remaining 1860’s sandstone barn that shares the same block as a 1920’s Tudor Revival home. Identify houses ordered from a Sears-Roebuck catalog, houses made entirely of steel, and the house Wright designed as a prototype.

Length: Approximately 1½ hours  

West Rail Corridor

In the 19th century, the West Rail Corridor, the area around the Milwaukee Road Depot on West Washington Avenue, was a hotbed of businesses that depended on the railroad to transport raw materials and finished products, as well as businesses that served railroad passengers and workers. This area, birthplace of a number of long-term Madison businesses, now abounds with repurposed historic buildings that are home to offices, renters and condo owners. Join us for a nostalgic, up-close look at Madison's railroad history through many architectural gems.

Length: Approximately 1 hour 45 minutes