City: Chicago, IL

Category: Parks & Recreation

Insider Pick:

Description: Hit this 18½-mile paved linear path for a mostly uninterrupted stretch along the Lake Michigan shoreline. It connects neighborhoods from Rogers Park to Hyde Park for biking, running, walking, and marvelous people-watching. Wherever you pick up the path, you’ll pass interesting sights: sunbathers lounging at beaches, games of recreational beach volleyball, pups bounding into the water to fetch balls at the doggie beach (Belmont Avenue), intense chess matches at the retro-styled chess pavilion (North Avenue), picnicking and grilling, dining at the only lakefront outdoor restaurant (Oak Street Beach Cafe; 312-915-4100), and views of the daredevil-piloted planes and jets of the annual summer Air and Water Show. Rent two-wheelers, tandem bikes, or four-person surrey bikes at several stops along the way too. If you’d rather not compete for space on the fairly narrow trail (speedster cyclers can sometimes rule the road here), then we suggest you get out early when it’s magically quiet and you can watch the sunrise over the lake.