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Oshkosh, Wisconsin Travel Guide

I LOVE Oshkosh. I went to college there so I'm a little biased. But every time I go back to visit, I remember just how much fun I had back then. The city is beautiful and covers ground near Lake Winnebago, Lake Butte des Morts, and the Fox River, making it the perfect destination for days on the water. Oshkosh is approximately 80 minutes northwest of Milwaukee and 90 minutes northeast of Madison. Here are some things you need to do in Oshkosh, Wisconsin.


SLEEPING ARRANGEMENTS

Take advantage of the waterfront views while you're in town! We stayed in an absolutely gorgeous AirBnb during our weekend trip. Tjs Destination Oshkosh owns several rental properties in the city and we experienced Hickory on The Lake located on the shores of Lake Winnebago. The property is 3 bedrooms, 3 bathrooms and SUPER conveniently located. We watched both the sunrise and sunset from the backyard and relaxed in the four seasons room. I cannot recommend this lodging option enough!


FOOD & DRINK


When I was attending college in Oshkosh, I ate a lot of Jimmy John's, Polito's Pizza, Big Apple Bagels, and Rocky Rococo's. While Polito's is still one of my favorite pizza spots in Wisconsin, my taste buds have matured juuust a bit. Here are some of the spots we ate at during our stay.


Gabe's Wisconsin Kitchen and Tavern did not exist back in my day but WOW I wish it had. They are known for their beer can chicken and we made sure to take advantage. We ordered the Beer Can Mac & Cheese, Southwest Salad (with Beer Can Chicken), and of course an order of cheese curds made with Ellsworth Creamery cheese. The restaurant itself was very welcoming and started gaining quite a crowd by the time we left - that's a sign of good eats.


Ardy and Ed's Drive In is an Oshkosh staple. They have a such a fun menu with tons of classics and they will deliver food right to your car on roller skates! We enjoyed our ice cream on their patio area and took their famous draft root beer to-go. The restaurant has been around since 1948 and has won dozens of awards for the delicious food and old-school vibes.


If you know Oshkosh, you know there are a lot of great dive bars. We had to visit at least one! We checked out Jockey Club which is a recently remodeled bar and restaurant with a beautiful outdoor patio. They serve daily specials, an awesome fish fry, and have tons of TVs inside for you to enjoy while sipping on a cocktail. All of the bartenders and patrons were extremely welcoming!


Elsewhere Market and Coffee House is located right downtown and is a definite must-see. I will cover the market portion in the "shopping" section, but their coffee is SO GOOD. They serve regular coffee, iced coffee, and Vietnamese coffee. It is to die for. Their menu also includes sandwiches and baked goods for you to enjoy while relaxing in their gorgeous space.


Caramel Crisp and Café supplied us with Sunday breakfast: breakfast sandwiches, iced coffee, and their famous cookies. They make SO MANY desserts, but are originally known for their gourmet popcorn. There are over 15 flavors to choose from! The café serves different menu items for breakfast, lunch, and dinner. I can confirm that their breakfast sandwich is pretty yummy.


SHOPPING

While you're grabbing some eats at Caramel Crisp & Cafe, check out their toy store, bookstore, and giftshop! Their toy store has everything from stuffed animals, games, art supplies, puzzles, and more. I couldn't believe how big it was! The gift shop has tons of Oshkosh-branded items and other boutique goodies. It's the perfect place to grab a keepsake!


Wagner Market is one of the coolest spots in Oshkosh in my humble opinion. Inside you will find a deli, a butcher, 100+ different cheeses, and 500+ different varieties of craft beer. Excuse me, what?! It took us so long to decide what we wanted to try, but each time I made a lap through the store, I found something new! There is just so much to look at and choose from - you won't leave empty handed.


I mentioned Elsewhere Market & Coffee House earlier, but now I want to focus on the market side. Attached to the coffee house you will find a beautiful store stocked with home goods, gifts, and other locally sourced finds. Grab your coffee and head on over to do some browsing, you won't regret it.


The Oshkosh Farmer's Market is AMAZING. There are over 165 local vendors selling items such as fresh fruits and veggies, flowers, crafts, and more! We loved checking out all of the different booths and even taste-tested some kombucha. I bought a loaf of cheese-bread, a smoothie, and a bouquet. There is live music and food stands, too! The perfect way to start your Saturday morning.


GET OUTSIDE

Cruisin Tiki's in Oshkosh is only a few years in the making and WOW I wish it existed back in my day. You can rent a private tiki boat for 2-hours and enjoy views of the city while in the water. They do multiple themed tours throughout the day so you are guaranteed to find one that fits what you enjoy. The boats take off from Fox River Brewing and allow you to purchase food and beverage from the restaurant to bring on board! We brought some cheese curds on our ride. It was PERFECT!


Sawyer Creek Nature Preserve is a beautiful area located on the outskirts of Oshkosh. There are a few trails that run through the preserve and they are perfect for a mid-day stroll. The area is so green with trees, flowers, and other plants and includes a small, quiet creek. We took a break from our eventful visit to spend time here and it was a great spot to recharge.


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