The western end of the Bloomingdale Trail offers the fewest major attractions, though that should quickly change with the opening of the 606. Spilling out into middle of the Humboldt Park neighborhood and the edge of Hermosa, the Ridgeway Trailhead (built on the four-acre site of a former glove factory) will be a great starting point for exploring an area rich with Hispanic culture and history. Walt Disney was born nearby. There is no shortage of tacos. Off Color Brewing is one of the most creative Chicago breweries going. Weegee's Lounge is one of the great dive bars. Make your way to the terminus of the 606.
RECOMMENDED: Our complete guide to the 606