Looking for some fun Valentine's Day activities? Whether you plan to spend your Valentine’s Day with family, or looking to take your sweetheart on a date night out - check out the many things to do in Oshkosh!

Things to Do with the Entire Family

Downtown Oshkosh Chocolate Stroll - Saturday, February 12th

Downtown Oshkosh is excited to announce their 1st Annual Chocolate Walk! This event is sure to satisfy every sweet tooth as each stop will have a delicious chocolate treat for you to enjoy. Spend the Saturday with your sweetie or family in Downtown Oshkosh. Plan to come down early for lunch, then enjoy the stroll with shopping at your great Downtown stores and a delicious treat at each.

Winter Flight Fest at EAA - Saturday, February 12th

Winter Flight Fest will feature both familiar and new cold-weather attractions for attendees. From 8 a.m. - 4 p.m., kids and those young at heart can enjoy hands-on activities, interactive exhibits, virtual flight simulators, and special events, including the Skiplane Fly-In.

Candlelight Cross-Country Ski/Hike - Saturday, February 12th

Join the Oshkosh Rec Department for a magical evening cross-country skiing or (or hiking, depending on snow) along a 1.5 mile candlelit trail. Admission is FREE. Pre-registration is required. Bring your own equipment. Limited equipment will be available for first time skiers to try on a first come first serve basis. 

Herd Game - Tuesday, February 15th

The action packed Herd games are filled with fun giveaways, a chance to meet the players, and loads of family fun entertainment! The Herd culture is definitely something you do NOT want to miss out on. 


Grab some Sweet Treats


Things to Do with a Significant Other

Paint by Candlelight at Fire Escape - Saturday, February 12th

Memories are sure to be created at Fire Escape! Book a reservation and paint by candlelight for an awesome date night experience. Choose your project when you arrive and decide if you want to work on a couples project or work on something individually - maybe to gift to one another!

Valentine Partner Yoga at Embody Yoga and Pilates - Saturday, February 12th

Partner yoga is a fun, interactive way to experience yoga. This workshop is for couples, friends or family members of all levels, no yoga experience required. Afterward, we will sample wine and Oaks chocolates. Bring your partner and have some Valentine fun!

TJ's Highland Steakhouse meal for two - February 11, 12 & 14

Flirt with flavors this Valentines Day at TJ's Highland! $175 for 2 includes a 3-course meal and a choice of red, white, or bubbles. Check out their Valentine's Day course options here!

Valentine's Day at The Hangar - February 14

Valentine's Day Menu will be offered Monday, February 14th from 11am-9pm. Now accepting reservations, 920.233.7430. Check out their Valentine's Day menu options here!

The Wine Down - Amore Edition at The Gibson Social Club - February 14

The Wine Down at the Gibson returns with a themed, amore edition, in honor of the holiday of love. Ticket price includes a specially curated wine flight, decadent charcuterie, live music, and an exclusive experience at Elsewhere Market.

Enjoy this date night evening with your Valentine, Galentine, Palentine, or with a small group of your dearest. Purchase tickets here.

Ground Round 4-course meal for two - February 12-14

Make plans to join Ground Round at River’s Edge for a delicious and romantic dinner for two! Ground Round is offering a 4-course meal for two, which includes a bottle of wine or champagne for $79.99. 

Win a FREE Overnight Stay at the Best Western Premier Waterfront Hotel!!!

Treat your Valentine to the Romantic Escape Package at the Best Western Premier Waterfront Hotel & Convention Center in Oshkosh. This sweet deal features an overnight stay, a $25 Dining Certificate at the Ground Round at River's Edge, a Bottle of Champagne or Wine, & a Box of Oak’s Meltaway Chocolates. Package rates start at $154.99 (plus tax), available February 11-14, 2022. Call 855.230.1900 to book today.

Win a Romantic Escape Package - random winner will be drawn on February 6, 2022. Click here to enter ▶ https://bit.ly/32tpUqi 


For the Daddy Daughter Duo

Annual Daddy Daughter Dance at the YMCA - Saturday, February 12th

Don’t miss out on the chance to twirl your little girl around the dance floor. Dads and daughters will take part in an evening of everlasting memories including drinks, music, dancing, a photo booth + more FUN! Don’t forget to dress to impress for your keepsake photo.

There is SO much to do this Valentine's Day in Oshkosh! Let us know your 2022 Valentine’s Day plans!

Stay the night in Oshkosh—click here for overnight options!