Romantic Date Nights in Oshkosh, WI

Oshkosh is one of the most romantic cities in Wisconsin. With incredible restaurants dotted around the town and a thriving nightlife scene, you can have a unique and memorable date night with almost no effort at all. If you are looking to elevate your night and surprise your loved one with a date night for the books, head to one of these romantic spots around town. 


Grand Opera House

Treat your loved one to a grandeur night of red velvet, evening gowns, and incredible entertainment at the Grand Opera House in Oshkosh. Shows vary from smooth bluegrass bands to award-winning musicals to the Oshkosh Symphony Orchestra. Plan your night so that you arrive about an hour before the show to relax in The Grand Lounge upstairs. This full service bar is the perfect place to begin your night and marvel at the beauty of this historic opera house. 


Trout Museum of Art

Spend the day exploring the incredible collections at the Trout Museum of Art. This fine arts gallery in Appleton, WI hosts a rotating collection of exhibits and works from artists all over the world. The museum is open Tuesday-Sunday during the days, but on one special Thursday a month, jazz music will fill the halls during Jazz at the Trout. Listen to Wisconsin musicians play a wide variety of jazz music for a fun and unique date night.


Grab a Cocktail (or two) 

A date night doesn’t necessarily need to be an over the top occasion, just a simple outing is all it takes to reconnect with your favorite person in the world. Take a break and head out for a cocktail at one of Oshkoshs great establishments. From urban eateries to neighborhood gastropubs, there are some great bartenders just waiting to mix you up a drink. Read our post Oshkosh’s Best Craft Cocktails to find our favorite spots in town. 


The Howard

The Howard is a mix between craft cocktail bar, boutique eatery, speakeasy charm, and upscale bowling bowling alley. You’ll feel like you’re in The Great Gatsby as you sip on elegant craft cocktails in your grandeur lounge. Entertainment, food and drink all wrapped into one spectacular package! You can also keep an eye out for their unique events held in the Grand Ballroom or Great Hall. Enjoy whiskey dinners to jazz nights and even Havana Nights dancing parties that will keep you busy all night long. 


Backlot Comedy House

If you want to spend a night laughing until you’re crying and your belly aches, then head to the Backlot Comedy House in downtown Oshkosh. Every weekend this intimate theater fills up with people looking for an incredibly fun evening of entertainment. Catch one of their improv shows any weekend, or check out their event schedule to sign up for a seasonal show or an acting class.


TJ’s Highland Steakhouse

Sweep your loved one off their feet for a romantic dinner at TJ’s Steakhouse at the historic Oshkosh Country Club. Cozy up in a traditional Scottish lodge and dine on the finest cuts of meat elevated to perfection by their incredible chefs. Grab a cocktail or a bottle of wine off of their award winning wine list and sit back and relax in luxury. A date night has never been more delicious!


Time Community Theater

If you want a romantic dinner and a movie type of night, head to Gardina’s Kitchen-Bar-Market for a bite then walk across the street to the Time Community Theater. The theater shows movies from old time classics to documentaries and seasonal favorites in an intimate theater with a nostalgic feel. This 100 year old theater offers a personal experience that you just can’t get anywhere else. Grab some popcorn and enjoy your favorite movies the way they were meant to be seen – on the big screen. 


Stay at Brayton B&B

Whether you are looking for a little overnight staycation or a full romantic retreat, the Brayton Bed & Breakfast is the place to stay. Experience their classically charming rooms, some with luxurious amenities like plush four poster beds, soaking tubs, or additional living spaces. This grand inn is in the heart of downtown and within walking distance from the best restaurants, theaters, and attractions of Oshkosh. Explore the town, fall deeper in love, and return to your elegant rooms for a date night for the books. 


A romantic date night has never been easier (or more memorable). There are tons of romantic activities to do in Oshkosh so come for a Valentine’s weekend getaway, a special anniversary celebration, or simply to unwind with your favorite person in the world. 


Ready to go shopping in Oshkosh, WI? Book a stay at the lovely Brayton Bed & Breakfast, where modern luxury meets historic style.