Wisconsin Getaway Ideas: Oshkosh

“Wisconsin’s Event City,” Oshkosh is home to over 1,000 events and festivals, including the famous EAA AirVenture and the Country USA music festival. The city on the western shore of Lake Winnebago also has more than its share of year-round fun. Here are our top picks for an Oshkosh weekend getaway, any time of year. 

Where to brunch

Pilora’s Café dishes up the café essentials – friendly service and wholesome food – with a dash of originality. From jazz music in the background to some unusual menu items (like cornbread pancakes with Door County cherries and the Moroccan ham sandwich) Pilora’s makes a point of offering something different. They also brew Alterra coffee, so you can fuel up on a proper cup of joe before heading out for your Oshkosh adventures. 

Where to explore

The EAA’s AirVenture fly-in every August isn’t your only chance to experience Oshkosh’s world-renowned Experimental Aircraft Association. The EAA AirVenture Museum, open year-round, features over 200 historic airplanes, plus movie theaters, galleries, flight simulators, and two "hands-on" interactive galleries for all ages. 

Where to shop

You’ll find a lot of unique shops on (and just off) Main Street. A few to get you started:

If big-name stores are more your style, The Outlet Shoppes at Oshkosh, across from the EAA, is home to 55 of the best. We recommend adding a whole day to your Oshkosh itinerary if you want to hit the outlets! 

Where to get your culture on

The Grand Opera House, built in 1883, is the oldest operating theater in Wisconsin. It puts on a fun variety of entertainment, from the Oshkosh Symphony Orchestra to musicals, rock ’n’ roll shows, and karaoke nights. The Paine Art Center and Gardens is a 1920’s estate with an amazing art collection and display gardens. Their Family Discovery Gallery offers hands-on art experiences for children. Admission: $9 adult/$5 youth. 

Where to go for dinner

Gardina’s Wine Bar & Café has a great menu of American/Mediterranean starters, cheese plates, salads and sandwiches, with nightly entrée specials. But it’s their pizza that steals the show. Bring an appetite and brace yourself for some tough decisions: there’s an impressive selection of wines, craft beers, and – bonus – individual-sized cheesecakes. Jam to live music Friday and Saturday nights. 

Where to stay

The Brayton Bed & Breakfast is just a short walk from Main Street. Warning: if you stay in this beautiful, friendly B&B, you might not want to leave...especially on the weekends, when you can enjoy an afternoon wine and cheese social in the living room, and homemade desserts later in the evening. Rates: $99-$199 nightly. 

Learn more about all the fun Oshkosh has to offer here.

This entry was posted in City Getaways and tagged Accomodations, Antique Shops, Arts, Attractions, Bed & Breakfast, Entertainment, Food / Drink, Getaway