Riverside Weekend Getaway in Oshkosh, Wisconsin

Nestled along the shores of Lake Winnebago, Oshkosh, WI, is an easy weekend escape from Chicago or Milwaukee. Oshkosh has plenty of surprises for anyone looking for culture, great food, and a little small-town magic.

My husband and I spent a wonderful weekend there, and were amazed by how much culture, charm, and character this small city delivered.

Activities in Oshkosh

1. Paine Art Center and Gardens – The Nature of Light Exhibit

   The star of our trip! At night, the Paine gardens glow with a stunning illuminated art experience. This light exhibit is running from August 1 – October 26, 2025. During the day, the historic estate and manicured grounds are equally beautiful and perfect for a peaceful stroll.

2. Downtown Oshkosh

   A walkable downtown filled with shops, art, and cafes. We loved stopping into Elsewhere Market & Coffee House for lattes and unique home goods and browsing the other charming storefronts.

3. Oshkosh Public Museum

   A fantastic way to dive into the region’s history and culture. The standout for us was the Tiffany “Gardens in Glass” exhibit; it was absolutely beautiful and worth the visit.

4. Local Events

   We definitely recommend checking out all the local events in Oshkosh here: www.visitoshkosh.com/events/. We had a fantastic time at the Jazz Fest, which really brought the downtown area alive with music.

Tiffany “Gardens in Glass” at Oshkosh Public Museum

Where to Eat in Oshkosh

• Becket’s – A riverside restaurant that showcases stunning panoramic views of the Fox River. The menu combines creative, locally inspired dishes with a modern twist, making it perfect for a romantic dinner or a special night out.

• Truffle Pig – A newly opened Italian gem in Oshkosh that serves up house-made pastas, wood-fired flavors, and thoughtfully crafted dishes. The cozy, stylish atmosphere makes it an ideal spot for date night or lingering over a glass of wine with friends.

• Golden Nest Café – A bright and inviting breakfast and brunch spot that instantly won us over. With sunny interiors, warm service, and beautifully plated meals, it’s the kind of place you’ll want to start every morning in Oshkosh.

• Leon’s Frozen Custard – This retro drive-in has been a local staple for decades, and stepping up to the window feels like stepping back in time. The creamy frozen custard and nostalgic atmosphere make it a must-visit for a sweet treat and a taste of classic Wisconsin tradition.

Where to Stay

We stayed at the Oshkosh Marriott Waterfront Hotel, located right on the river. The views were beautiful, and the downtown location made it easy to walk to everything.

From illuminated gardens and awesome events to riverside dining and historic museums, Oshkosh is the perfect blend of culture, food, and small-town charm. Add it to your travel bucket list!

This blog post was sponsored by Discover Oshkosh. Opinions are my own.