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Top Oshkosh Places to Fall in Love

Oshkosh couples

Winter isn’t all that bad for love in Oshkosh.


?  While the itch for sunshine and travel increases in February, we want you to know there’s still plenty for couples to enjoy in Oshkosh during the cold months! Valentine’s Day is the perfect excuse to get out of the house and spice up your love life.

Whether you’re local or from out of town, Oshkosh has many romantic and adventurous date night options. Continue reading to learn what the Event City has to offer you and your partner!

The first Saturday evening of every month, Downtown Oshkosh celebrates art and entertainment with the Oshkosh Gallery Walk and Saturday Night Out activities.

The Gallery Walk shows off local artists and galleries inside local businesses.

Saturday Night Out offers art, shopping sales, art classes, food and drink, entertainment and more. For one night each month from 4-11 p.m., downtown local businesses stay open late for visitors to shop, eat and enjoy entertainment, such as a movie, comedy show or live music. Downtown Oshkosh will also be decorated in a “Love Your Downtown” theme all month.

Oshkosh Gallery Walk

The Oshkosh Gallery Walk happens every first Saturday of the month.


If you’re looking for an elegant date night with a cause as an added bonus, the Opera House Foundation is hosting its second annual A Grand Night gala event at the Hilton Garden Inn Oshkosh Feb. 18. Attendees will enjoy dinner and cocktails, entertainment, and silent and live auctions. Proceeds benefit educational, outreach and free community programming at The Grand.

Grand Opera House

Enjoy A Grand Night for a good cause!


Visiting Oshkosh from afar? We have plenty of romantic places for you to spend the night after a night out on the town!

Bed & Breakfast
Brayton Bed & Breakfast is located downtown near the University of Wisconsin Oshkosh and many restaurants and events. Guests enjoy a full breakfast and evening desserts every day as well as a wine and cheese social every weekend. Check out Brayton’s special packages and book your holiday!

Brayton Bed & Breakfast

Book a room at Brayton Bed & Breakfast for a more intimate stay.


Suites on the Water
Best Western Premier Waterfront Hotel & Convention Center is the newest hotel in Oshkosh. It offers guest rooms and suites with views of the Fox River and Lake Winnebago in the distance. Suites also have fireplaces and whirlpools for couples to enjoy together. Book your guest room or suite for you and your sweetheart today!

Best Western Premier Waterfront Hotel

Book a suite at the Best Western located along the Fox River.


Oshkosh has many restaurants as well as several breweries and wineries for couples looking for a unique date. Check out our list of top restaurants for couples in February:

Wine Tastings & Food
Gardina’s Wine Bar
Vines & Rushes Winery in Ripon

Beer, Tours & Food
Ruby Owl Tap Room
Bare Bones Brewery
Bar 430


Sip on fancy drinks at favorite Oshkosh bars and restaurants.


South of the Border

Manila Resto (Philippine dishes)
Sakura Japanese Steakhouse

Tamara’s The Cake Guru
Caramel Crisp Cafe (Best cookies in town)

Fine Dining
On the water
Fox River Brewing Company
TJ’s Harbor Restaurant
The Vintage

Brooklyn Grill
Mahoney’s Restaurant & Bar
The Roxy Supper Club


Pick from many Oshkosh restaurants for a delicious dinner.


There’s something for every couple to do in Oshkosh! From arts to entertainment, do something that you and your love will both enjoy. See our recommended list of things to do in the Event City this month:

Grand Opera House

Dress up and attend a theatre show at the Grand Opera House.


Arts & Crafts
Fire Escape (Downtown)
The Art Spot (Same building as Becket’s)

Time Community Theater (Downtown)
Marcus Oshkosh Cinema

The Backlot Comedy House (Sketch, improv and open mic)
Grand Opera House
Fredric March Theatre (College theatre)

The Backlot Comedy House

Have a good laugh at The Backlot Comedy House.

? What’s your ideal Valentine’s Day date in Oshkosh? ?
❤️ Tell us in the comments below! ❤️

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