Chicago is made up of 77 neighborhoods beyond the downtown Loop, and one of the best ways to explore several of them is the Bloomingdale Trail. Opened in June 2015, this 2.7-mile elevated linear park—often called The 606—follows a converted 1915 rail line and provides a wide, paved, 25-foot path designed for walkers, runners and cyclists of all ages.
Unlike a narrow nature trail, the Bloomingdale Trail features thoughtful landscaping, trees, water elements, benches and rotating public art installations. Thirteen ramps grant easy access across multiple neighborhoods, making the trail both accessible and convenient. The project was developed with support from the City of Chicago, The Trust for Public Land and other local partners.
Because of its similarities to New York City’s High Line, comparisons are common: Chicago’s trail is longer (2.7 miles versus 1.45 miles), allows bikes, and is surrounded by a wide range of dining options that many locals find less expensive and equally appealing. The 606 name refers to Chicago’s metro zip code prefix and also includes plans for connected ground-level parks, an observatory, a skate park and additional public artworks. The official 606 site provides an interactive map and up-to-date trail information for planning visits.
The western end of the trail bisects Logan Square and Humboldt Park. Logan Square is a lively mix of residential streets and businesses, served by several CTA Blue Line stations. The neighborhood is known for its strong culinary scene, live music venues and a popular Sunday farmers market. While in Logan Square, visitors often stop at City Lit Books for maps and local reading, grab a meal at Lula Café, browse upscale women’s fashions at Felt, or enjoy cocktails and Cajun-inspired fare at Analogue. For an overnight option with a neighborhood feel, the farm-to-table Longman & Eagle restaurant also operates six guestrooms on its second floor.
Humboldt Park celebrates a rich Latino heritage, visible in colorful murals and vibrant community life. The neighborhood offers a variety of Caribbean and Latin American eateries, including spots serving slow-roasted brisket tacos and bold regional flavors. For drinks, gin-focused cocktail bar Scofflaw is a popular choice on weekends and weeknights. Families and visitors with a sweet tooth often head to Roeser’s Bakery, in operation since 1911 and recognized as one of the city’s long-standing family bakeries.
At the trail’s eastern end are the well-heeled, trend-forward neighborhoods of Bucktown and Wicker Park. These areas are packed with boutiques, restaurants and nightlife. Shoppers can browse unique apparel at places like the RSVP Gallery, and diners can try eclectic fare at spots such as Dove’s Luncheonette. Wicker Park, known for its creative, independent spirit, also offers artisan doughnuts and live music venues such as the Double Door concert hall. Public art is woven into the trail experience as well, with installations at places like Damen Arts Plaza enhancing the route.
Overall, the Bloomingdale Trail functions as both a recreational corridor and a neighborhood connector, encouraging walking, biking and social activity while bringing renewed attention and investment to adjacent communities. Whether you’re looking for a casual stroll, a longer bike ride, dining options or arts and culture, the trail offers an accessible, scenic way to experience several of Chicago’s distinctive neighborhoods.