Chicago's Most Famous Alley Is An Enchanting Gold Coast Gem For A One-Of-A-Kind Glimpse Back In Time
Chicago's rich history reveals itself in unexpected ways. The city is full of architectural and cultural historic treasures, and sometimes that history is quite literally underfoot. Walking through the elegant Gold Coast neighborhood, past grand brownstones and tree-lined streets, you might come upon something unusual: A narrow alley paved not with asphalt or cobblestones, but with wooden blocks.
This is Wooden Alley, a relic of early 20th-century Chicago and one of the last remaining of its kind. In the 1800s and early 1900s, wood paving was a common sight in Chicago, thanks to the city's large lumber resources. However, most of these streets were replaced over time with brick or stone, as wood proved to be slippery and prone to decay. Today, the Wooden Alley is a rare survivor you can still walk over. You'll find it tucked between Astor Street and State Street in the Near North Side's Gold Coast district, just a short trip from downtown and close to Chicago's sought-after Lincoln Park neighborhood. It's closer than a 30-minute drive from O'Hare International Airport or easily accessible via the CTA's Red Line at Clark/Division or Brown or Purple Line at Sedgwick, followed by a short walk through the historic neighborhood.
The story of Wooden Alley and Chicago's wooden streets
Wooden Alley was added to the National Register of Historic Places in 2002. Though it's now a surprising sight, this alley was once part of a much larger network of wooden-paved streets. Chicago had 37 miles of wood-paved roads around the time of the Great Fire of 1871. The wooden pavers were made by Samuel Nicholson in the mid-1800s and had a few benefits: They were cheap (due to the large supply of lumber Chicago had), and they muffled the sounds of horse hooves and wagon wheels in the bustling city. While many assumed the fire would have destroyed them, most actually survived thanks to the wood's chemical treatments.
The Wooden Alley itself dates back to 1909, stretching 530 feet between Astor and State Streets. As time passed, however, most wooden roads deteriorated and were replaced with sturdier materials. According to a City of Chicago press release, only two wooden streets remain, making Wooden Alley an especially rare historical landmark.
Many of the original wooden streets were paved over, and occasionally, they are revealed during construction. But instead of waiting for roadwork to unearth Chicago's hidden history, you can simply walk down Wooden Alley and experience it firsthand. In 2011, the alley underwent a major restoration, replacing the decayed blocks with black locust wood, a naturally rot-resistant material to preserve the alley. Some of the original wooden blocks were also incorporated into the design, maintaining a tangible connection to the past.
Take in the historic buildings around Wooden Alley and the Astor Street District
More than just a relic, Wooden Alley is also a centerpiece of some of Chicago's most stunning historic architecture. The alley sits within the Astor Street Chicago Landmark District, a beautifully preserved area where you can avoid Chicago's tourist traps and take in some hidden historic gems instead. On the north side of the alley stands the Cardinal's Mansion, home to the archdioceses of Chicago. Built in 1885, this Queen Anne-style red brick mansion is hard to miss with its 19 chimneys and striking facade. Walk further south along Astor Street, and you'll find the Charnley-Persky House, a distinctive building designed by Louis Sullivan and a young Frank Lloyd Wright in 1892. The home blends intricate ornamentation with geometric simplicity, a perfect example of Sullivan's famous "form follows function" philosophy. Tours run year-round — and if you go on a Wednesday at noon, admission is free.
One way to experience the Wooden Alley and the historic district is by making a day of walking the Lincoln Park Trail, which loops through the Astor Street District and around Lincoln (Abraham) Park. The route takes about 90 minutes if you do it on foot, but you'll likely want to linger at some of the area's must-see attractions. A short walk north of Wooden Alley brings you to Lincoln Park, home to the free-admission Lincoln Park Zoo and the Chicago History Museum, perfect for capping out a unique day exploring the city's past. For more Chicago history, check out Pullman National Historical Park, the city's first national monument.