Madison's 'Bohemian, Hippie' Street Is A Walkable Wisconsin Fun Zone Of Shops, Restaurants, And Festivals

The city of Madison has a reputation as one of the nicest places to live not only in the Midwest, but in the whole country. Home to a large university and situated between two lakes, Madison is ranked as Wisconsin's happiest city and is also often referred to as the "biking capital of the Midwest." This laid-back burg boasts a rich arts and culture scene, America's largest producer-only farmers market, and over 270 parks that all add up to create a remarkably high quality of life.

While you can experience these charms throughout much of the city, the 10-block stretch of Williamson Street, also known as "Willy Street," is a terrific place to explore, as it exudes the relaxed, bohemian vibe that this city offers in spades. With historic old homes, a classic theater, funky shops, and great food — along with a park that hosts two of the city's best festivals — this district is Madison at its coolest and most intriguing. It's also perfectly suited for exploring on foot, as it is one of Madison's most walkable neighborhoods.

Extending from Machinery Row Bicycles — just a stone's throw from the Wisconsin State Capitol — to the Yahara River, Willy Street is more than just a road. It's an entire district of sorts, situated in the Marquette neighborhood. Willy Street acts as a vital lifeline for this area, surrounded by Victorian and Craftsman homes that speak of Madison's rich history.

Start your visit to Willy Street by doing a bit of shopping. Pop into the St. Vincent de Paul store for some good ol' fashioned thrifting, pick up some custom handcrafted gifts at Hazel General Store, or browse the vintage toys and collectibles at Meep Meepleton's World of Fun. If you need a sugar or caffeine boost to keep you going, swing in for some pastries fresh out of the oven at Batch Bakehouse, or sit down for quality coffee at Mother Fool's Coffeehouse, which embraces the district's hippie spirit with organic drinks, vegan baked goods, open mic events, and art exhibitions.

For entertainment paired with history, check out a show at the Barrymore Theater, one of Willy Street's most iconic landmarks. Built in 1929, this 971-capacity venue features live music, independent films, standup comedy, and more. While perhaps a bit worn-in, this is a building that certainly retains its classic charms. "The theater is one of those really cool old-style venues," remarked one visitor on Tripadvisor. "It has a funky sort of feel that works perfectly in Madison. Quite frankly, it really reminds me of the places that were around in my college days in the late 60's and early 70's."

While rich in shopping and entertainment choices, Willy Street's greatest selling point may be its food. Home to around 20 eateries serving everything from French fare to Southeast Asian cuisine, there are plenty of quality options along this bustling corridor. For impeccable quality, start with Sardine at the street's far western end. Specializing in French and American seafood dishes, it is regarded by some as one of Madison's top restaurants. The Weary Traveler Freehouse is a tavern-style bar and restaurant that serves what one Redditor called the "best burger in Madison," while Grampa's Pizzeria does artisanal thin crust pies.

For a taste of Japan in the Midwest, dive into a savory bowl of noodles at Umami Ramen & Dumpling Bar, or take a culinary trip to Laos at Ahan, run by a pair of chefs that includes a James Beard Award candidate. The green curry and red curry udon dishes are delicious, according to a restaurant reviewer at the Milwaukee Journal Sentinel. 

If you're looking for green space, just a few blocks over from Willy Street is Yahara Place Park. This 6-acre expanse is the perfect place to relax and while gazing out at the shimmering waters of Lake Monona and the Yahara River. The park also hosts two of Madison's biggest summertime celebrations. The Marquette Waterfront Festival is a two-day live music event held in mid-June every year, while the Fête de Marquette celebrates Bastille Day for three days in July with music, community engagement, and plenty of French cultural activities.