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I traveled with my family to Oshkosh, Wisconsin where they provided complimentary experiences and comped my stay to facilitate my article. Do you know what to say when someone asks you what do to in Oshkosh?

Fun activities in Oshkosh Wisconsin

Where is Oshkosh, Wisconsin?

Oshkosh is a small town in Wisconsin on the Fox River in Winnebego County. Conveniently located just off Interstate 41, it’s about 75 miles north of Milwaukee and a bit south of Appleton.

Under three hours from downtown Chicago makes this a perfect weekend getaway. It’s also easily accessible from Minneapolis.

Yes, this is where Oshkosh B’Gosh was founded, too. The town has way more to offer than just this brand, however.

Oshkosh has become known as Wisconsin’s Event City because they have so much going on. Many are activities you can enjoy throughout the year, while others have special events at specific times.

What to Do in Oshkosh, Wisconsin

On the Loos Cruises

Oshkosh is right on the river, and On the Loos Cruises leaves from the river walk right next to the Best Western. They provide cruises each Tuesday, Wednesday, and Friday through Sunday starting in mid May through the end of warm weather.

Loos Cruise Oshkosh paddleboat

The two hour cruises cost just $35 per person. Most are family friendly, with the exception of the 8pm cruises on Friday and Saturday nights – the earlier cruises those days are open to all.

The paddleboat heads up the Fox River from the river walk to Buttes Des Morts and back again. It’s a slow cruise with little wake, so there’s no need to be concerned if you’re prone to seasickness.

The cruise includes some complimentary snacks for passengers ranging from trail mix to cookies to chips. There is also a full bar with drinks available for purchase.

One of the most fun parts is that you can actually captain the paddleboat. Captain Jeff stays right with you and ensures you know what you’re doing, but you can and for real do steer the boat. My kids both took advantage of this opportunity and absolutely adored it.

Steering a paddleboat

This is a perfect low key way to enjoy and explore Oshkosh. Unlike some boat cruises, you don’t have a constant narration of what you see, but crew members are around and happy to answer any questions you may have. As locals, they pretty much know it all!

Head out to Terrell’s Island

When the weather cooperates in Wisconsin (and it does more often than you might expect), a hike along the water is a perfect way to spend a few hours. Terrell’s Island is located just 25 minutes from downtown Oshkosh by car, and it is gorgeous.

Terrells island

The four mile trail takes out out along Lake Buttes des Morts – near where you traveled with On the Loos Cruises – in a loop with water surrounding you along with gorgeous plants and birds and more. We saw butterflies and turtles and bumblebees ducks and and dragonflies and more as we walked.

Bumblebee on Terrells Island

The trail is pet friendly, though you must keep your dog on leash from April 15 to July 31 to protect nesting birds during this time. Outside those dates, you may take your dog off leash, so long as your dog stays under control and doesn’t bother others. I don’t need to remind anyone to pick up after your dog, right?

Along the trail, you’ll find several benches installed as part of an Eagle Scout project, which provides nice breaks along the way.

In addition to hiking, you’ll find bikers on the trails. You can also canoe and kayak from Terrell’s Island, as they provide multiple launches along the way. You do need to bring your own, however, as there are none here to rent.

Visit the Paine Art Center and Gardens

If you have any interest in history whatsoever, you need to visit this mansion. Originally built by the founder of the Paine Lumber Company based in Oshkosh. The Paine family never lived in the house, which wasn’t completed until after the death of Nathan Paine.

Paine Center of the Arts and Garden

The house opened as a museum with as much historically accurate furniture and items collected by the Paines as possible. In addition, you can find an arts center with rotating exhibitions so there’s always something new.

Rotating Paine art exhibit

Don’t miss out on the gardens, which are almost more impressive than the house. The 20 acres include a variety of gardens and styles, which have many hidden treasures.

Our favorite was a planter with kaleidoscopes that used the flowers to create the fractured images. You’ll find everything from a formal English Tudor symmetrical garden to a shade garden and everything else English you can imagine.

Paine Garden Kaleidoscope

Each weekend, the Paine provides a fun art project for visitors at no cost. The weekend we visited, my daughter and I had the chance to make sun changing bracelets and sun exposure pictures with items from the garden. This is a fun add on for kids as they join you to explore the mansion and grounds.

Paine Center art project

The Paine is open daily 10am to 4pm. Adults cost $12 for admission to the mansion and gardens, while Children 5-12 cost $7, and those 4 an under are free.

You Can’t Miss the EAA Aviation Museum

Even if you’ve never visited Oshkosh before, you have have heard about the EAA AirVenture. It’s held at the airport the last weekend in July each year, and they average over 100 takeoffs and landings each hour with more than 10,000 aircraft at Wittman Regional Airport and surrounding airports.

When the week long air show ends, there’s still plenty to see and do at the EAA Aviation Museum. Open 7 days a week from 10am to 5pm, this is a fantastic experience for kids and adults.

Vintage biplane

The museum includes a ton of airplanes and replicas from the start of aviation history, as well as an interactive area for kids where they can learn about everything from force to the Bernouilli Principle and more in a fun way.

EAA Aviation Museum KidVentures

We spent only a few hours at the museum, and that was not nearly enough to enjoy it all. Plan to spend an entire day exploring.

Beyond the main building of the museum, visitors can take a tram to Pioneer Airport that houses more vintage airplanes to explore, along with a few other vehicles.

The big draw for that area, however, is the opportunity to take a flight. Both my children took the free Young Eagles Flight offered by EAA volunteers. 

EAA Young Eagles flight

This flight requires a waiver signed by a parent, and kids then take a flight on a first come, first served basis – weather permitting. The kids take an approximately 15-20 minute long ride, and they have a chance to fly the plane for part of the time.

My daughter got off the plane and decided she wants to be a pilot. She’s taken advantage of the EAA offer for the free Sporty’s Learn to Fly course for online lessons and is plotting how to get me to pay for the remainder of her flight lessons.

Adults also have the chance to take a flight. For $75 per person, those 16 and over can ride in a vintage bi-plane. It’s a fantastic and unique experience!

A family with two adults and up to five children can explore the museum for just $31. Otherwise, adults cost $12.50, with seniors (62+) and veterans and active duty military are $10.50. Students 6-17 cost $9.50, with those under 6 admitted free.

Head to the Farmer’s Market

My town has a farmer’s market. I’ve been to farmer’s markets in Chicago and elsewhere. The Oshkosh farmer’s market puts them all to shame, honestly.

Open every Saturday from June through October – as well as Wednesdays from mid-July to mid-September, they keep it going even in winter with an indoor market held select Saturdays from November through April.

The downtown outdoor market we visited had over 130 vendors from the expected fruits and vegetables to baked goods and hot food and more. It went on for multiple blocks, to our surprise.

Oshkosh farmers market

Make sure you reserve enough time to slowly wander and explore all they have to offer. You’re sure to find something – or somethings – to love, and it’s fun people watching, too. Select vendors offer samples to tempt you into purchasing, and I can verify that they work!

Interestingly, we saw signs at all entrances stating that no dogs are permitted, but we saw several dogs on leashes as we walked through the farmer’s market. That said, leave your dog at home for this one!

Have you ever visited? Do you have advice on what to do in Oshkosh?

5 ideas for what to do in Oshkosh Wisconsin: great family activities for a weekend getaway, including 3 free ideas. Enjoy a girlfriends weekend or a couples vacation. It's easy to get to from Chicago or Milwaukee, too! #oshkosh #vacation #getaway #traveltips

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  • Vickie

    Thanks for the nice article about my hometown. Just one thing. Oshkosh is not a small town. It’s 70,000 people. (Compared to Chicago, yes it’s small, but it’s a city, not town, and definitely not small). We may have a small-town feel, but we’re not small.

    Glad you enjoyed your visit! Hope you come back soon.

    • Michelle

      You make a good point. To me, 70,000 is still a small town, but it’s all a matter of perspective, and I get your point. (The town I live in is pretty close to that size, and I call this a small town, too) It was definitely a fun visit, and we’ll be back again for sure. I’m glad you enjoyed the article – small town mention, aside!

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