Oak Street Beach, Chicago

Back in the late 1800s, Chicago's Lake Shore was all peace and quiet, gently sloping from Oak Street to the Chicago River and providing a serene haven for Lakeshore property owners. Then along came George Streeter, a Civil War veteran, carnival enthusiast, steamboat captain, and the brassiest of con-men. His boat, the Reutan, packed with cargo and passengers, found itself marooned on a sandbar.

Now, most folks would've been flustered by such a mishap, but not our George, who decided to get creative! He took that stranded ship, its cargo, and a heap of trash, and voilà, he conjured up a small island, declaring it his very own ship-trash-pier-sand island. Naturally, this led to some heated disputes, including good old-fashioned gunfights. Long story short, George was eventually given the boot. The land he left behind was filled in and got christened Streeterville, which just so happens to be the present site of the 360 Chicago Observation Deck and the illustrious Chicago Water Tower.

Back in the day when this area was a resort, the legendary Drake Hotel made its grand debut in 1920 as a beachfront property. Guests could effortlessly saunter from the changing rooms on the arcade level straight onto the sandy shores. Sadly, the construction of Lake Shore Drive separated the beach from the neighborhood, but fret not – a nifty tunnel ensures easy access, and it remains a primo spot to plop down your towel and take a refreshing dip. Since the sand is in short supply, locals have mastered the art of spreading out on towels along the concrete walkway and taking the plunge when things heat up. And if you fancy a bike ride, a pit stop for snacks, or a visit to the restrooms, you're in luck – these amenities are available seasonally, along with changing rooms, bathrooms, volleyball courts, plus the Oak Street Beach Restaurant, which offers a casual (though somewhat pricey) menu, along with great views of the lake and skyline.

So, there you have it, the story of Oak Street Beach, complete with battles, beachfront hotels, and a whole lot of sun-soaked fun!