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 circle towards the back of the the Center, you’ll come upon a massive lawn that overlooks Lake Michigan. You’ll find folks picnicking on the grass and enjoying the cool breezed coming off the water.
Right in front of the lawn is a small beach with life guards on duty. In normal times this would be open to the public, but for now, it’s closed off. The only exception is to cross the beach to our next spot, the South Shore Nature Sancutary.
Being able to easily access natural space, no matter where you are in the city, is an important topic when it comes to building a more connected and equitable Chicago. When it comes to nature reserves in city, the South Shore Nature Sanctuary is a beautiful space that community advocates have long fought hard for.
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.
Keep following the path as it meanders across 6 acres of dune, wetland, woodland, prairie, savanna and shrubland habitats
At a certain point, the path will take you towards the tip of the peninsula where you’ll uncover two limestone fire circles available for anyone to use.
One of the fire circles sits near the edge of the water, where the just past the natural vegetation, you can find an unobstructed view of the Chicago skyline.
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. 