Visiting Oshkosh, Wisconsin

Oshkosh, Wisconsin, might be best known for its namesake children’s clothing brand, but this Fox River city offers so much more than overalls.

Located between Lake Winnebago and Lake Butte des Morts, Oshkosh is full of small-town charm with an artsy, adventurous edge. Especially in the summer, the city comes alive with riverside dining, boutique shopping, and outdoor experiences that make it the perfect Midwest weekend escape.

Discover Oshkosh hosted Chad and I for a weekend of fun in the sun, and we made the most of our first-ever visit to Oshkosh. We can’t wait to return!

Whether you’re into exploring gardens, sipping wine flights, or paddling across a sparkling lake, Oshkosh delivers. Here’s a fun-filled summertime itinerary for your next visit.

About Oshkosh

Oshkosh is located in east-central Wisconsin, about 90 miles north of Milwaukee. This 67,000 city is home to Lake Winnebago (Wisconsin’s largest inland lake), Fox River, an incredibly charming downtown, University of Wisconsin Oshkosh, and the Experimental Aircraft Association.

Our Oshkosh summer weekend itinerary

We fit a lot of fun into a summer weekend in Oshkosh; here’s how we spent a Friday through Sunday in central Wisconsin.

Friday

Dinner and live music at Fox River Brewing Company

Our first stop was to Fox River Brewing Company, where we enjoyed dinner and drinks on the outdoor, riverfront tiki-themed patio. There was live music, incredible harbor views, and a fun, laid-back atmosphere to kick off our trip.

Also, my chicken wrap was delicious!

Drinks at Flights

We loved swinging by Flights Wine and Cocktail Club for an outdoor happy hour—a chic and cozy spot across the river, near downtown. We sat on their outdoor patio and ordered our flights: old fashioneds for me, wine for Chad.

They also have charcuterie board options.

Stroll and shop downtown

Downtown Oshkosh is extremely walkable, lined with art and independent shops—it’s easy to shop and support local! Many spots are open late on weekends, and there’s a range of everything from home goods to clothes, souvenirs to vintage records.

Late-night movie at Marcus Theatres

There’s something about a late night movie! Chad and I snuck away to Marcus Theatres for a showing of the F1 Movie, complete with popcorn, snacks, and reclining seats.

Marcus Theatres started in Wisconsin, so we always love supporting them when possible. It was also nice to know that Oshkosh has options available for late-night fun.

Saturday

Coffee from New Moon Cafe

We started our full day in Oshkosh with a caffeine fix at New Moon Cafe. It was a cozy and artsy corner spot in downtown, bustling with energy and a delicious vanilla latte.

Oshkosh Saturday Farmers Market

Next, we stepped into the Oshkosh Farmers Market, which takes over the entire downtown. We were SO impressed: the crowds were strong, as vendors lined up throughout several blocks. There was a mix of goods, including fresh produce, baked goods, crafts, jewelry, food trucks, and flowers.

It was an incredible showing, made even better by live music playing throughout.

I highly recommend stopping by the farmers market if you get the chance!

Paine Art Center & Gardens

Afterward, we visited what would be one of our top highlights of our Oshkosh trip: the Paine Art Center and Gardens.

Inside the historic estate, there’s a mansion with preserved interiors and public art galleries with a rotating exhibit (we loved learning about Native American basket weaving) to explore in a self-guided format.

Outside, botanical gardens abound. There are gorgeous landscapes, flowers, ponds, and chirping wildlife. It’s beautifully maintained, and feels like a romantic set straight from Bridgerton.

We loved every moment exploring the Paine Art Center and Gardens, and I highly recommend making it a priority activity!

Kayak at Menominee Park

We immediately gleamed that Oshkosh is a hub for water-centric fun—a playground for boating, fishing, swimming, kayaking, and more. To lean in, we decided to visit Lake Winnebago and see what the fun was about for ourselves.

At Menominee Park, we found self-serve kayaks to rent for only $20 for two hours! It was super easy and involved using the Rent.Fun app—learn more here. As huge kayak lovers, this activity was right up our alley.

Chad and I had an incredible time with our kayaks, paddling, floating, and admiring fish and birds. It was peaceful and easy, and another highlight of our visit.

Pro tip: be sure to explore Menominee Park! It’s home to playgrounds, baseball fields, pickleball and tennis courts, picnic spots, open spaces, and the Menominee Park Zoo—a free entry home to over 40 animals.

Lunch at Bar 430

After a full morning of activities, we stopped by Bar 430 for lunch and drinks. In addition to a beautiful space, we loved our food! I ordered a very on-brand lavender mule to go with my southwestern salad.

Riverwalk

Oshkosh has a lovely riverwalk, perfect for exploring! It’s great for anyone looking to get a little exercise, get in the water, or simply admire the Fox River flowing by. There are about 3.5 miles of completed Riverwalk, with opportunities to fish, sit, dine, or walk, with unique sections along the way. There are also kayak and canoe launches, along with public docks.

Overall, the Riverwalk is a great place to enjoy the many features of the Fox River.

Dinner at The Roxy Supper Club

For dinner, we opted to try the classic and iconic Roxy Supper Club. Located on Main Street downtown, the Roxy was exactly as a supper club should be: nostalgic, hearty, affordable, and delicious. Chad and I both enjoyed steaks served with an old fashioned, as tradition demands, making for a perfect end to our day.

Sunday

Coffee stop at Elsewhere Coffee

Before heading out of town, we stopped by Elsewhere Market and Coffee House in downtown Oshkosh. Elsewhere was modern, cute, aesthetically pleasing, and attached to a boutique full of high-quality goods.

Most importantly, the coffee at Elsewhere was delicious! I enjoyed a refreshing and delicious lavender latte with soy.

Brunch at TJ’s Harbor

Food-wise, we stopped by TJ’s Harbor, a casual restaurant a little ways outside of town. TJ’s had an incredible outdoor patio space, and we enjoyed eating our plates and drinking our $4 bloody marys (they were delicious!) with an incredible lake view.

The vibes were great here! It was a laid-back way to enjoy a weekend brunch.

Shop the Oshkosh Outlet Mall

Our last stop before hitting the road was to the Oshkosh Outlet Mall. With all of the usual suspects—Nike, Old Navy, Gap, Eddie Bauer—we walked away with some great (and discounted) brand name finds.

Discover and explore Oshkosh

After a weekend visit, it’s clear that Oshkosh packs a big punch when it comes to summertime fun, with plenty to do, see, eat, drink, and enjoy.

From jumping into Lake Winnebago (okay, floating on top of) to perusing a lively downtown, Oshkosh is a bit of a gem, hiding in plain sight in central Wisconsin. I can’t wait to return!

---