10 Ways to Enjoy Chicago’s Lakefront Trail

Along the shoreline is Chicago’s Lakefront Trail, a paved pathway stretching 18.5 miles (29.7 kilometers) along the city’s coast. Unlike the lake, which might still be freezing cold by the time summer rolls around, the path is open 24 hours a day and accessible year-round. There’s a lot to do along the Lakefront Trail, but here are 10 popular activities to get you started.

Okay—yes, duh. Walking along a trail is pretty obvious. But a leisurely stroll can turn into an exciting, athletic activity pretty quickly in Chicago. First of all, anyone interested in some of the most picturesque views of the skyline should snap some shots from the Lakefront Trail near Montrose or Belmont Harbor, looking south. Second, a walk presents more opportunity for spontaneity. Urban hiking has become hugely popular in recent years, and the Lakefront Trail acts as a great home base for a trek in the Windy City. Veer off toward the Lincoln Park Zoo or the Museum of Science and Industry (two of many sites accessible by foot from the trail). Walking along the trail is also a very eco-friendly way to check out all that Chicago has to offer.

Anyone who loves biking and nightlife will be stoked to hear that there’s an electric bike tour to take in the evenings along Chicago’s Lakefront Trail. Companies like Bobby’s Bike Hike take groups along the trail, stopping at trail-accessible spots like Soldier Field and Museum Campus, all while riding electric bikes (which makes this much easier for those less familiar with biking in a city setting). The entire tour typically lasts about 2.5 hours and covers eight miles (12.8 kilometers) of ground. Seeing the fireworks at Navy Pier or the Buckingham Fountain lit up at night is a real treat and a super special way to experience Chicago and its shoreline.

There are four parks accessible via the Lakefront Trail, each offering unique sites and Instagram-worthy landscapes. Lincoln Park is full of playgrounds for kids, the always free Lincoln Park Zoo, and the Lincoln Park Conservatory, a spectacular botanic garden with a lily pond and wildflowers. Grant Park, near the downtown Loop, hosts music festivals during the summer months and offers visitors gorgeous gardens through which they can stroll or ride.

Burnham Park, near Soldier Field, has a model boat pond, a stone beach, and a skate park area. It also links Grant Park to Jackson Park, the former site of the World’s Columbian Exhibition of 1893. Within the 500-acre expanse of Jackson Park is the Garden of the Phoenix, a Japanese garden built in 1933, complete with an enormous koi pond.

The Lakefront Trail acts as a giant, outdoor museum. Artists display their work throughout the year here as part of a rotating collection of sculptures and figures. For a brief time, artist Tom Friedman’s 33.3-foot-tall (10.1 meters) sculpture Looking Up, which is made of aluminum foil, baking pans, and used tins, sat along the lakefront before moving to a permanent home in St. Louis.

Anyone using the trail should also be on the lookout for pieces from the Chicago Tree Project, an art movement in which artists turn dead or dying trees into sculptures, representative of environmentalism and taking care of nature. There are roughly 30 tree sculptures on display—and many more sculptures to view along every block.

There is no shortage of sand along Lake Michigan and the Lakefront Trail. From north to south and back again, visitors are guaranteed to find a sunny spot for a beach towel and a break. Oak Street Beach offers up spectacular views of the city. North Avenue Beach usually hosts intramural volleyball games for anyone in the mood for watching a little competition. Feel like playing your own game? Head north to Montrose or Hollywood Beach for tons of space to set up nets or toss a ball around. Or use the pedestrian underpass below the Museum of Science and Industry to reach 57th Street Beach off Jackson Park. Here you’ll find concessions, restrooms, and again, plenty of sun.

If running is too rough on the knees, rollerblading is an excellent cardio alternative. It’s hard to miss the hoards of people taking their exercise regimens to the shoreline. Why not get in on the action? Stations in both Navy Pier and Lakeview offer rollerblade rentals. Again, rollerblading is like biking in that it takes you farther, faster so that you can pack more of Chicago into your day. Plus, rollerblading along the trail is sure to work up a sweat. Roll right off the sidewalk and onto any one of the many beaches along the city’s lakefront for a dip in Lake Michigan. You can also try rollerblading the Ribbon in Maggie Daley Park, a gorgeous raised pathway accessible through Grant Park.

There are several beaches in Chicago open to dogs, which is a welcome treat to canines everywhere. Montrose Dog Beach is open all year during Chicago Park District hours, and it was the first off-leash dog beach in the city. Be sure your pup is up to date on vaccinations and immunizations! Belmont Harbor Dog Beach is pretty tiny and surrounded by boats, so be aware of your dog’s whereabouts the entire time. Foster Avenue Beach actually has a dog wash station, which is essential for anyone planning on plopping their pup into a car afterward. Whether a dog owner or a dog lover, these are the trail stops you’ll want to remember.

Between April and October, tennis enthusiasts can get in some sets at Tennis on the Lake. This company has been offering tennis lessons along Chicago’s Lakefront Trail for 17 years. Not interested in a full lesson? Maggie Daley Park has six tennis courts available to visitors free of charge. If you know exactly when and how long you’ll want a court, you can also rent one ahead of time starting at $15 an hour.

A historic property right on Lake Michigan near Fullerton Avenue is aptly called Theater on the Lake. In this gorgeous green building, patrons can experience live theater, music, and events like beer tastings or social galas. There’s also a fine-dining venue, The Lakefront Restaurant. The romantic space seats 125 with unmatched views of the lake and cityscape at sunset. Be sure to check the restaurant’s website before planning a dinner date here—it may be booked out for a wedding or special event. If reservations are available, book away. This place is definitely a perfect one in which to end a day after exploring Chicago’s dazzling Lakefront Trail.