In a small town with the population of a mere 6,000 people, rests the Caribbean of the Midwest. I grew up in this place, Waupaca, Wisconsin, home of the incredible Chain O’ Lakes. However, these aren’t just any old Midwest lakes. You’ll find the same bright blue water that you would in Fiji (trust me, I know). Equipped with hot summers and mojitos on the docks of your favorite restaurants, Waupaca is the ultimate getaway. With that being said, I have a few must-sees for those who are unfamiliar with this small town.

Check Out Marl Lake

Marl Lake
Marl Lake

My suggestion for you is to start at Marl Lake. Here, you’ll find a small, public dock unknown to most people besides the few locals. You can swim in the deep water on a simmering day or start your kayak journey through the Chain O’ Lakes. Since the 22 lakes are all connected, you can go as far as your arms can paddle!

Rent A Boat

Boating Chain O' Lakes
Boating Chain O’ Lakes

If you’re more into relaxing than exercising while on vacation, rent a boat from one of the marinas. There are plenty of sand bars to anchor at and enjoy a picnic on the water. If you’re not much of a planner, you can actually pull right right up to the dock of Clear Water Harbor on Taylor Lake and have your lunch served in style.

Listen To A Live Band

Surprisingly enough, small towns still have great gigs! You might get lucky and enjoy a floating band while having lunch at Clear Water Harbor. Otherwise, you can stop by the Indian Crossing Casino. And, no, this is not the gambling kind of casino that you’re used to seeing. It’s a newly renovated building that you can dock your boat up at or simply come from the parking lot the old fashioned way. There’s food, a full bar and great views all right on the water. You can watch for their upcoming events and concerts here.

Scream for Scoopers

Scoopers Ice Cream
Scoopers Ice Cream

Scoopers is one of the most well-known places in town. Every spring, we would sit in class and refresh our browsers, waiting to see that “Scoopers is now open for the summer!” post. Scoopers is an ice cream shop near the Indian Crossing Casino and right next to the Wheelhouse Restaurant, my favorite dinner spot in town. They have tons of flavors here and it’s really inexpensive for how large the portions are. Honestly, I can never do more than the kids scoop! 

Grab A Coffee From Red Mill

Red Mill
Red Mill

Red Mill is an old mill house along the river that’s also newly renovated and beautifully so. There’s a great cafe here with incredible coffee and ice cream made in Madison, Wisconsin’s capital. Personally, I think this ice cream is arguably even better than Scoopers, but, hey, that’s for you to decide. Make sure to stop at the gift shop on your way out. It’s here where you’ll find bags of homemade taffy or those old peppermint sticks you used to love while growing up. Afterward, take a walk along the river’s bend below with your sweet treat of choice.

Enjoy A Hike At Hartman Creek State Park

Growing up, I used to bike to Hartman Creek after school every day to go on hikes around the lake or swim at their small beach. If you’re feeling more adventurous than the traditional tourist cabin rentals on the Chain O’ Lakes, you could also rent a campsite at this park. It’s a really nice area to relax, fish, hike and lay low for a few days. There are also electric sites available, so you won’t have to go full-on ghost mode. 

Kayaking Crystal River
Kayaking Crystal River

If you’re not convinced of Waupaca’s charm yet, email me because we need to have a chat! From the blue waters to the hot summers and ice cream checkpoints, there really is no way to go wrong while stopping by the Caribbean of the Midwest. If you have any other questions or need advice on planning your trip, feel free to reach out or comment below! I’d love to help. 

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