Only in Oshkosh: 10 Ways to Make the Most of Your Visit

Adri & Kam
Sep 21
4 min read

Looking for the best things to do in Oshkosh, Wisconsin? This vibrant city on the shores of Lake Winnebago is packed with one-of-a-kind attractions, local events, and outdoor adventures you won’t find anywhere else. Whether you're planning a weekend getaway or building your Oshkosh travel guide, these 10 unique experiences will help you make the most of your visit. Discover what makes these Oshkosh attractions truly unforgettable.

Try Italian food at Truffle Pig

This restaurant is the city's newest hot spot, and it's all the locals can talk about-for good reason. We absolutely love the vibe that makes you feel as if you were in Italy along with delicious dining options. They also have a bar where you can grab a fancy cocktail before dinner. I personally loved their wood -fired pizza which made my taste buds very happy. Reservations are highly encouraged!

Enjoy outdoors at Asylum Point Lighthouse

With its lighthouse and stunning views, this spot is perfect for a quick walk, a longer, relaxing visit, or even some fishing. Locals mention it is one of the best spots for fishing. Either way, the lighthouse makes for an awesome photo opp 😊

Learn all about planes at EAA Aviation Museum

Not sure if you knew, but Oshkosh hosts one of the largest airplane gatherings. It is a one week long event that sees the most airplane traffic than anywhere in the world! How wild is that?! If you’d like to learn more about the history of aviation and see where the festival takes place, make sure to take your time here. You can easily spend a couple hours here and for those that are 17 or younger, you may even have a chance to fly in one of their planes for free! We were able to see a couple of kiddos go on this adventure, which makes for the perfect family friendly activity.

Take an evening stroll at Paine Art Center & Gardens

Whether you are visiting the gardens in the morning or evening, they will not disappoint. However, now through October 26^th, they are hosting The Nature of Light exhibit, which is a MUST! Sculptures and lights interwine, forming mesmerizing shapes that will levae you in awe the entire time. If you do anything in Oshkosh, this place must be it!

Grab apples at Redmond’s Orchard

Now that it is fall time, it’s the perfect season for apples. Even though you cannot pick your own apples here, you can still purchase freshly picked ones and they are so delicious! This orchard is family owned, and they also grow their own pears which are just as great. Check out their little shop and pick up a peck of apples this season!

Savor all types of wines at Vines & Rushes Winery

We sure love a good winery, and this place delivers some of the best wines we have ever tried. The winery is set on a family farm 30 minutes out of downtown Oshkosh and is perfect for casual visitors or wine lovers. The tasting room offers all kinds of wines including ciders, which are amazing pairs with their Neapolitan style pizzas that are baked in a brick oven. Staff are superb and willing to share everything they know about their wines. So, enjoy a glass of wine or a flight if you’d like to try more and relax with the great scenery this place shares.

Explore Murals/Street Art

Photo ops are what we love about any city, that way we can capture colorful content to showcase you! Oshkosh is full of fun and creative art that can be found all over the city. Some of our favorite ones can be found at below addresses:

Emma Daisy Mural – 440 N Main St

Algoma Alley – 110 Algoma Blvd

Greetings from Oshkosh – 571 N Main St

Fifth Ward – 1009 S Main St

Take your taste buds on an adventure with Golden Nest

We believe a good day starts with a great breakfast- and Golden nest made sure ours was off to the perfect start for exploring. Their pancake flight was divine and everything I have been dreaming about since we came back. Kam had a South of the Border skillet, and he left no crumbs behind. Even though they were super busy, we did not have to wait for our food for long and enjoyed every bit of it.

Delight yourself in fine dining at Gardina’s

Gardina’s is located right in the middle of everything, so it’s the perfect spot to grab lunch or dinner and walk around from there. It’s not only a restaurant, but also a wine market with tons of variety to pick from to take home with you. The restaurant’s warm and welcoming vibe creates an ideal setting for a date night, or a family get together. Highly recommend ordering their Strawberry Chamomile Paloma and Prime New York Strip along with Beet and Whipped feta Dip as an appetizer.

Indulge in a wine flight or a fancy cocktail at Flights Wine & Cocktail Club

If you are looking for a nightcap or a cocktail before dinner, this place is the perfect spot for it. We loved the cozy ambiance, and the staff was lovely as well. They have a full bar and a big variety of wine that you can try in a flight or a glass. We certainly enjoyed our beverages after driving from Chicago and right before dinner.