1. South Shore Cultural Center
To get things started, let’s talk logistics. The South Shore Cultural Center is directly on the path of the Lakefront Trail. From Downtown, it’s an easy 45 minute (9 mile) bike ride if you can resist making stops to snap pictures of the skyline.
If biking isn’t in the cards today, the Metra Electric District train from Downtown will drop you off in front of the South Shore Cultural Center in about 25 minutes. You can also drive onto the grounds and park in a public parking lot that costs $2/hour.
As you enter the grounds, you’ll come upon a long entryway that takes you to the front of the South Shore Cultural Center. Built in 1905 as an exclusive country club, this served as the center of social life for the community’s elites. Over the next 70 years, the demographic make up of the community changed, but the club’s insistence that it exclude the community’s largely Jewish and then African-American residents, never wavered, and it ultimately led to the clubs dwindling membership.
The club finally shut down in 1974 and the property was sold to the Chicago Park District after a hard fought battle by community advocates to preserve the space and turn it over to the people.
Today, it’s a community space for the arts, music, and cultural programs that are open to everybody. With current COVID-19 restrictions in place, the building itself is closed off to the public, but you can still walk the grounds and admire the structure’s Mediterranean Revival style architecture from the outside.
If you close your eyes, you can almost feel the history of the place and imagine the types of opulent, Great Gatsby-style of parties that must have taken place here.
As you continue to walk the grounds, you’ll immediately notice that a majority of the property is set aside for a 9-hole golf course. This is operated by the Chicago Park District and open to the public. It’s about $18 per golfer, which seems like a good deal — I wouldn’t know, because I’ve never golfed a day in my life but that seems legit.
What I can attest to, however, is that you’re not going to beat these types of views from the tee box.


As you make your way from the beach and into the nature santuary, the sand gives way to a path that leads you to a wooden boardwalk surrounded by native grasses and wildflowers.





If you come better prepared than us, bring along a few logs and make use of the fire pit as the sun sets across the city.