48 Hours in Oshkosh

It’s the weekend. Finally. And you are ready to go exploring and check out a new place. Bags are packed and Oshkosh is the destination. You’re on your way when you realize, you don’t know a thing about the town. Where are you going to eat? What attractions do you want to see? Everyone has made the mistake of waiting until the last minute to find a restaurant and choosing the wrong one, or missing out on a major attraction simply because they didn’t know about it. Luckily, you don’t need to be an Oshkosh expert to explore the town because we are and are willing to give you all of our secrets to exploring this great city.


The first secret to a perfect weekend is making sure you hit all the must-see stops, without overbooking yourself and allowing for some downtime and spontaneous adventure. If you’re coming into Oshkosh by plane, car, or boat, you’ll find that the first thing you want is a nice centrally-located room to set up in and a place to grab dinner. Brayton Bed & Breakfast is an elegant, modern B&B in the heart of Oshkosh and walking distance to all the major attractions in the city. Arrive at your destination, check in with ease, and start your Oshkosh experience in the center of the town! Walk down Main Street and you’ll find yourself at Los Jaripeos, a classic Mexican restaurant with a colorful interior and equally colorful entrees. On your way back, stop at one of the several taprooms or boutique bars for a craft drink or a locally brewed beer. Turn in early for the night or experience more of the nightlife in Oshkosh. Either way, your return to your room will be greeted with homemade desserts waiting for you at the door.


Day 1:

Wake up in the morning to the smell of coffee and breakfast. Served each morning from 8:30-10, you can enjoy a homemade hot breakfast with no effort. Expect savory egg dishes or sweet entrees like stuffed french toast, and a plethora of fruit, baked pastries, and juices. After an amazing meal like that you’re now ready to start the day and explore the city.

Visit the Zoo

The Menominee Park Zoo is always high on the list for anyone visiting Oshkosh. This free zoo is located right on the waterfront and is a great little stop to see some exotic animals and view the lake. The park also rents paddle boats you can head out on the water, paddle around a little and enjoy the lovely Wisconsin summer weather!

Lunch at Ardy & Ed’s

An Oshkosh favorite since 1948, Ardy & Ed’s Drive In is a blast from the past. Expect roller skating carhops, 60’s hits, frosty milkshakes, and smiles all around. Sit in your car and enjoy the full service, or head over to the picnic tables to enjoy your delicious food outdoors. For a really nice treat, take the food to-go and walk to the public boat landing & park on Lake Winnebago for a perfect summer picnic.

Military Veterans Museum

Travel down south after lunch to the Military Veterans Museum to see artifacts and displays from different points in American military history. See a tank that was manufactured during WWII and deployed in Mongolia where it sustained multiple blows. Peruse the small arms and artillery collection including several weapons used in past wars. Learn about our history by touring through the several wonderful exhibits and memorials within the museum.

Head Downtown:

Main Street has several shops with cute trinkets, wonderful clothing, and antiques galore! One must-see is Crescent Moon Antiques & Salvage. Find collectible home decor items and stunning antiques, but the truly unique aspect of this store is the salvage aspect. There are reclaimed building materials, old barnwood pieces, and vintage windows that are perfect for any home remodel or building project.

Honestly, hours could be spent at Crescent Moon digging through all of the great items, but once you finally pull yourself away, you’ll probably be hungry for dinner. Gardina’s Kitchen-Bar-Market is the place to go for innovative, new-American fare. If you could only eat one meal in Oshkosh, one of Gardina’s signature dishes would be the way to go. Fresh ingredients, beautiful presentation, and mouth-watering flavors make for one amazing dish.

To finish the night, walk along the Oshkosh Riverwalk, take in the late Wisconsin sunsets, and appreciate the lights of the town on the river.

Day 2:

Once again, the wonderful smell of coffee and homemade breakfast will pull you out of bed. Find an entirely different breakfast spread in front of you, yet just as satisfying as the day before. Put on some sunscreen, finish your coffee, and head out for your second day in Oshkosh.

OshKosh Public Museum

Walk, or drive, past the University of Wisconsin-OshKosh to see some beautiful campus architecture on your way to the Oshkosh Public Museum. You’ll know when you arrive at the museum. Set in the beautiful Sawyer home, the Tudor style building is truly a sight to behold. Venture inside to see some wonderful exhibits ranging from Native American appreciation to Apostles Clock, to the gallery of glass and ceramics.

Paine Art Center & Gardens

Exit the museum and walk across the street to the Paine Art Center & Gardens located in a preserved historic estate with a mansion and botanic gardens. Tour the mansion and view the lovely art on display. Wander through the gardens and smell the fresh flowers in bloom. Learn about the architecture of the unique buildings on the property.

Caramel Crisp Corner for Lunch

Grab an early lunch at the Caramel Crisp Corner. Marvel in their classic, mouthwatering deli sandwiches but make sure to save room for dessert. The sweet treats coming out of this cafe are unparalleled. Their perfect chocolate chips cookies will melt in your mouth and their gourmet popcorn is a perfectly unique treat created to be enjoyed on Sunday afternoons. This downtown establishment is a local favorite for the past 85 years. With a candy, toy store and gift shop, this is the ideal stop for guests of any age.

On the Loos Cruise

When in Oshkosh, a Loos Cruise is a must. These paddlewheel riverboat tours are the perfect afternoon activity. Enjoy their Sunday Funday cruise which takes off from downtown Oshkosh at 1 pm and lasts about 2 hours. The perfect amount of time to see the Oshkosh shoreline and float around on Lake Winnebago! The captains are wonderfully charming and will fill you in on some of the most interesting facts about Oshkosh!

Grab a Slice at Ratch & Debs Pizza 

Unfortunately, your 48 hours in Oshkosh are coming to an end, but that doesn’t mean it has to end on a low note. Stop by Ratch & Debs Pizza, an authentic Green Bay Packer Bar and restaurant on your way out of town and grab one of their signature pies and a local Wisconsin craft beer. Filled up with good food, good beer, and good memories, you’ll be missing Oshkosh before you’ve even left!


If you have some extra time or are willing to travel a little further outside the city, we recommend meandering through the EAA Aviation Museum, touring the Vines & Rushes Winery, biking the Wiouwash Trail, or sampling some of Wisconsin’s best cheeses at Henning’s and the Union Star Cheese Factory. Oshkosh has so much to experience that 48 hours is barely enough, but this wonderful city will always leave you wanting more. So come back and say hi anytime.


Planning a trip of Oshkosh, WI? Book a stay at the lovely Brayton Bed & Breakfast, where modern luxury meets historic style.