Between Madison And Cedar Rapids Is Wisconsin's 'City Of Presidents' With A Walkable Downtown And Antiques

Wisconsin may often go overlooked by travelers, but it's brimming with picturesque small towns, historic charm, and walkable downtowns. One such example is tucked away just an hour-and-a-half from both Madison, the "biking capital of the Midwest," and Cedar Rapids, making it an easy day trip or weekend getaway while in Wisconsin. Cuba City, which has a population of just over 2,000 people as of 2023, is home to a quaint Main Street and a number of antique shops, ideal for laid-back travelers.

Cuba City's roots trace back to the 1830s, before Wisconsin even became a state. Over the next few decades, the land changed hands a couple of times, and businesses began to sprout up, from a roadside inn to a general store. After a railroad station was constructed in 1874, Cuba City was officially able to become a town — there was only the matter of deciding on its name. The town's name was debated at length, and eventually, the name "Yuba" was chosen after the Yuba River in California, which held personal significance to one of the town's co-founders. However, it was later discovered that the name Yuba was already taken in Wisconsin, so the name was changed to "Cuba." In the 1920s, it finally became "Cuba City," which has stuck.

Cuba City is also called the "City of Presidents," thanks to the line of shields depicting the U.S. presidents found along Main Street. The original shields were created for the country's 200th birthday in 1976, and continue to add historic flair to Cuba City's downtown. To get to Cuba City, a limited number of flights operate out of Dubuque Regional Airport, located roughly 30 minutes from town by car. Chicago O'Hare International Airport is the closest major travel hub, and the drive to Cuba City is just under three hours. 

Cuba City's downtown can be explored easily on foot. Its Main Street stretches for just over a mile, and is dotted with local shops, quiet green spaces, and cozy restaurants. Along the way, don't forget to keep an eye out for the 46 presidential shields adorning Main Street. Be sure to stop by Gile Cheese Factory Outlet, a Cuba City staple since the 1940s, for a distinctly Wisconsin souvenir. Among its over 140 locally-made — and in many cases, also award-winning — varieties, you'll discover everything from Wisconsin cheese curd, nearly 30 types of cheddar, specialty cheeses, and much more.

Just a block away is one of Cuba City's most-loved eateries, Nick's Cafe, which serves breakfast and lunch. "Best homemade food hands down," wrote one visitor on Google. "No one can ever compare! This needs to be your number one stop if you're ever in the area for some yummy food and amazing service." Right around the corner from the cafe, you'll see the Presidential Plaza, home to a vintage railroad car and caboose, a scenic gazebo, and a visitor's center dedicated to the town's railroad history. For some outdoor recreation, Splinter Park is less than a 10-minute walk away, with numerous athletic fields, courts, and a playground for the public to enjoy. 

Similar to Whitewater, another underrated city for shopping in Wisconsin, Cuba City boasts a number of antique shops. In fact, South Main Street has been dubbed "Antique Avenue," thanks to its plentiful shopping for vintage keepsakes. At Junque Stops Here, browse a range of antiques, folk art, furniture, and more, sourced by over 35 local dealers. Antiques Unlimited, which has been around since 1982, also offers an assortment of jewelry, glassware, furniture, dolls, and other goods. If you're looking to add vintage touches to your home, Antiques & Salvage is also a local favorite, with a 4.7 rating on Google. The shop specializes in architectural items, ranging from windows to doorknobs, and also sells furniture and other vintage items.

For more of the city's best shopping, don't miss Cuba City's community market, which runs every third Wednesday of the month from May through September at Veterans Memorial Park. Here, you can enjoy music, family activities, and plenty of local shopping, from craft items to desserts. If you're looking for another picturesque town with a walkable downtown and tasty cuisine, also consider adding Greendale to your Wisconsin itinerary.