Bucktown and Wicker Park Bike Ride: Milwaukee Avenue and the 606

Two ways in, one neighborhood. The elevated trail lifts you above the traffic; Milwaukee Avenue puts you in the middle of it. This ride uses both. It belongs with the other Routes & Trails, and the full trail has its own Bloomingdale Trail guide.

The 2013 map

In 2013 the Chicago Bike Station at Millennium Park offered free maps of self-guided rides, including one for Bucktown and Wicker Park¹. The same list covered Lincoln Park, the Lakefront, Lincoln Square and Wrigleyville and Andersonville¹. See the Lincoln Square ride and the Wrigleyville and Andersonville ride for those. The station no longer runs rides.

The 606 above the streets

Bloomingdale Trail is a 15.6-acre, 2.7-mile elevated linear park running east–west along Bloomingdale Avenue³. It opened on June 6, 2015³. The Chicago & Pacific Railroad built the line in 1873³. The surface is concrete, with a blue rubberized running path on each side³. The trail runs between Ashland Avenue and Ridgeway Avenue³.

The 606 park and trail system is open every day from 6 a.m. to 11 p.m.⁴. The trail runs about 20 feet above street level⁵. More than one million people use it each year⁵. It connects to four neighborhood parks at ground level, an observatory and art installations⁴. E-scooters are not allowed, and Divvy stations stand nearby⁵.

An extension is planned to be completed by late 2027³.

Wicker Park

Exit the trail at Damen Avenue and walk to Six Corners, the bustling heart of Wicker Park⁵. The neighborhood sits in the West Town community area². Its northern edge is the 606 itself². Ashland Avenue forms its eastern edge, Division its southern edge and Western Avenue its western edge². The neighborhood holds the 4-acre Wicker Park, a Chicago Park District space². Brothers Charles and Joel Wicker bought 80 acres along Milwaukee Avenue in 1870². Hoyne Street was once known as Beer Baron Row². Much of the neighborhood is a Chicago Landmark District, and the historic district joined the National Register on June 20, 1979².

Bucktown

Bucktown sits directly north of Wicker Park⁹. Fullerton Avenue is its northern boundary and Western Avenue its western one⁹. The name comes from the goats raised here in the 19th century⁹. Horween Leather has stood on North Elston Avenue since 1920⁹. Its churches include St. Hedwig’s Church and St. Mary of the Angels⁹.

Milwaukee Avenue by bike

Milwaukee is a popular route for bicyclists⁸. At its southeastern end, cyclists made up 22% of all traffic on one September day⁸. Streetsblog Chicago called it Chicago’s busiest biking street in 2023, a direct route from the Northwest Side to the Loop⁶. It is also dangerous: more than 300 crashes took place between North and Western from 2018 to 2022, over half of them involving people on bikes⁶.

In 2017, CDOT counted that some 40 percent of the vehicles on the stretch were bicycles during the morning commute, and said most of the stretch would not get bike lanes in the near term¹⁰. The plan changed. In October 2023, protected lanes, raised crosswalks and bus islands were under construction on Milwaukee between Armitage and Western and between North and Damen⁷.

Segment	Design shown in June 2023
North/Damen to Western	Curbside lanes, protected by concrete curbs, plastic bollards or parked cars6
Western to California	Another sub-one-mile protected segment, which the new lanes connect to7
Speed limit	Reduced from the 30 mph default to 20 mph6

The stated goal in 2023 was an uninterrupted safe route on Milwaukee, from Devon Street to the avenue’s southern end in the West Loop⁶.

Putting the ride together

Start on the 606 at Ashland, ride west, and exit at Damen for Six Corners. Take Milwaukee southeast, where protected lanes were under construction in October 2023. The CTA Blue Line runs beneath and alongside Milwaukee from Canal and Lake Streets to Logan Boulevard⁸, so a tired rider has a train. Next, try Lincoln Square, or see Chicago bike lanes.