Check out a curated list of some of our Oconomowoc favorites. These spots have something going on year-round. From historic exhibits and charming shops to local events and lakeside dinners, here are six must-visit spots to start exploring!
1. Oconomowoc Historical Museum
First up, a quick step back in time at the Oconomowoc Historical Museum, celebrating 100 years this year! This museum welcomes visitors of all ages to connect with the area’s rich history through hands-on exhibits, fascinating artifacts, and more!
A few must-see exhibits? The Streets of Old Oconomowoc and the impressive Milwaukee North Western model railroad layout. And new this February, a brand-new exhibit takes the spotlight… From Fowler Lake to Devil’s Hollow: Winter Sports in Oconomowoc!
This special exhibit dives into the community’s deep roots in speed skating and ski jumping, along with Oconomowoc’s unique ties to Olympic history. Did you know Oconomowoc was the first site for the U.S. Olympic Speed-Skating Time Trials?
In addition, the museum offers fascinating presentations throughout the year on topics that showcase the community’s vibrant past. And for the history buffs out there, the Hilbert Scherffius Research Center unlocks access to an incredible archive of photographs, documents, and records detailing the stories of Oconomowoc and its neighboring communities.
2. Wisconsin Avenue
Next up on our off-season adventure, head downtown and take a stroll along Wisconsin Avenue, the heart of Oconomowoc!! If you’re looking to sip, savor, and shop your way through the city, this is the perfect place.
Oconomowoc’s Downtown shopping district has a great mix of shops that include women’s fashion, children’s boutiques, and artistic spots with items that make amazing gifts. All that shopping calls for a lunch break!
Just a short stroll away, Sobie’s Restaurant is a farm-to-table favorite that always hits the spot. Serving breakfast, lunch, and dinner, Sobie’s is known for its fresh, seasonal ingredients and creative takes on classic comfort food.
3. Wisconsin Brewing Company Park
From one happening hub to another, make your way to Wisconsin Brewing Company Park, home of the Lake Country DockHounds! This spot is packed with more family fun than you can imagine!
Want to keep shopping? Plan your visit around the Winter Farmer’s Market, happening February 8th and 22nd and March 8th and 22nd from 10 am to 2 pm. It features unique offerings like fresh produce, baked goods, handcrafted gifts, and seasonal items. There’s always something new to discover, too! Each market brings a brand-new mix of local vendors.
And when you’re ready to wind down, stick around for Dockhaus Night at The Dockhaus Brewery & Restaurant, starting at 5 pm. Gather your crew for free bingo and trivia, or check out their lineup of one-of-a-kind events, including the all-new Cribbage League & Tournament.
4. Lago Su Bella
For a meal that’s just as memorable as the view, make plans to dine at Lago Su Bella, acclaimed as the spot for authentic Italian cuisine in Oconomowoc. This family-owned favorite sits along the picturesque shores of Lac La Belle, adding a splash of charm!
The menu features handcrafted pastas, fresh seafood, and one-of-a-kind specialties, all made with simple, high-quality ingredients. Pair your meal with a glass from their thoughtfully curated wine list, and be sure to save room for dessert! Their tiramisu has earned local legend status for a reason.
Whether you’re celebrating a special occasion or simply savoring a quiet evening by the water, Lago Su Bella captures the essence of Lake Country dining. It’s a must-visit any time of year, but there’s something extra special about enjoying it in the off-season.
5. Newport 1875
From the same talented owner behind Lago Su Bella, Michael Bertrand, comes another can’t-miss dining destination—Newport 1875. Right in the heart of downtown, this new addition, coming soon, brings an elevated fine-dining experience to Lake Country.
Drawing inspiration from the flavors of France, Italy, Spain, Greece, and Portugal, the menu brings global flair to Wisconsin charm. Each dish is crafted with fresh ingredients, bold flavors, and a touch of creativity. Add in the unmatched atmosphere, exceptional service, and top-notch wine list, and trust us, you’ll want to stay awhile.
Newport 1875 is quickly making its mark as one of Oconomowoc’s most exciting new restaurants, perfect for date night, dinner with friends, or whenever you’re in the mood for something special.
6. Mon Bijou Inn
Wrap up your day at Mon Bijou Inn, a historic boutique hotel tucked right in the heart of downtown. Inside, the new Chandelier Lounge feels like a little getaway, all warm lighting, soft music, and that iconic chandelier.
Grab a seat at the bar or settle into a cozy corner with a handcrafted cocktail in hand. Go classic with an Old Fashioned or try one of their seasonal creations. They’re all mixed with care and just the right touch of flair! Add a few small plates to share while you unwind. It’s simply the perfect ending to a Lake Country day.
Want to make it a true getaway? Stay right upstairs in one of twelve boutique suites. Each offers a peaceful, private retreat where you can relax after a day exploring everything Oconomowoc and the Lake Country area have to offer in the off-season.
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If you haven’t spent time in Oconomowoc during the off-season, consider this your sign. It’s calm, it’s cozy, and it’s packed with lots of things to see and do, just without the summer crowds! Let these six spots be your starting point.
Ready to see Oconomowoc in a whole new season? Sit back and enjoy this Discover Wisconsin episode, “No Place Like Home — Oconomowoc”:
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Hailey Marien: Writer for Discover Mediaworks. A born & bred Wisconsinite with a love for fishing, hunting, and enjoying the great outdoors.
