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
What to do off the 606 at the Ridgeway Trailhead
The Ridgeway Trailhead marks the western end of the 606, which runs east through Logan Square, Bucktown and Wicker Park before ending at Ashland Ave. The land surrounding the trailhead will serve as the future site of a park, which will be built in the space formerly occupied by the Magid Glove Factory.
Ten years from now, when this strip of Armitage is populated with coffee shops and vintage clothing stores, this old-school, soul record–playing, classic cocktail–mixing bar will be overrun with hipsters vying for their turn in the photo booth. Start hanging out here now so you can say you knew it in the good old days.
The counter service café cranks out hot, crispy, cinnamony tube treats. The churros are fine as is, but you can crank it up a notch with fillings—vanilla, strawberry, chocolate, cream cheese or the flavor of the day, which can range from guave to the eggnog-like Rompope. Wash it down with coffee, or go all in with milkshake.