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
Fall in LOVE with Handmade Urban Craft Fair - Saturday, February 7
FREE! Take the family out for a shopping day! The Fall in LOVE with Handmade Urban Craft Fair at Becket's in Oshkosh is hosting over 40 vendors & live music! Plus - a portion of the booth fees will benefit The Oshkosh Area Humane Society. Join from 10am - 2pm.
Winter Flight Fest at EAA - Saturday, February 7
Winter Flight Fest will take place at the EAA Aviation Museum on Saturday, February 7, and will feature indoor excitement, and family-friendly activities. From 8 a.m. to 4 p.m., kids and those who are young at heart can enjoy hands-on activities, interactive exhibits, and more! Concessions will be available for purchase from 11 a.m. to 2 p.m. (The skiplane fly-in and free chili lunch portions of Winter Flight Fest have been cancelled).
Downtown Oshkosh Chocolate Stroll - Saturday, February 14
Downtown Oshkosh is excited to announce their 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. Tickets are $22 and allow you to stop for chocolate samples at 15 participating businesses! Get tickets here!
Sweethearts and Sweetarts Valentines Family Event - Saturday, February 14
Enjoy fun, interactive stations at Vines and Rushes Winery -- including sugar cookie decorating, face painting, a craft and coloring table, and a festive photo station to capture the memories! Valentine stations from 10am - 1pm, food service will be available from 11am–8pm, with live music from 2pm–5pm.
Grab your favorite beverage, enjoy delicious food, and spend the day making sweet Valentine’s memories with your little ones.
Visit the Love Shack at Fox River Brewing Company - Pop up!
The Love Shack is decked out with over-the-top festive décor, professionally crafted Valentine's Day cocktails, delicious eats and more! The Love Shack is a pop-up Valentine's Day bar inside of the Fox River Brewing Co. Taproom! Stop in to check it out before the season ends!
Grab some Sweet Treats
- Everybody loves Chocolate! Click here to learn more about our two famous chocolate shops in Oshkosh - Hughes and Oaks!
- Grab some fun Popcorn Flavors at two of the best popcorn shops in Oshkosh! Click here to learn more about Caramel Crisp and OshPop!
- Pick up a sweet treat for your sweetie, or pick up a fun Valentine’s Day dessert for the whole family at Tamara’s, Yetti Yums, or Sweet Jules!
Things to Do with Your Sweetheart or Gal Pals
Downtown Oshkosh Galentine's Day - Saturday, February 7
Check out the participating businesses offering sweet deals and specials just for you during Downtown Oshkosh Galentine's Day. A day of shopping and activities, check out each location to get your punch card stamped for a chance to win a grand prize worth over $500. From 10am-2pm visit: Brinkley's Boutique, Sugar Rushlow Boutique, Sweet Jules Bakes, 143 Expressions, Market Boutique, Can Can, Blonde Russian, Periwinkle Poppy Boutique, Turquoise Door, Soiree, Boutique by Urban Esque & Pivot Nutrition
Sweet Treats & Charcuterie - Sunday, February 8
Details: Sunday, February 8th from 10:00 AM – 2:00 PM -- Galentine’s Day vibes --Recommended ages 13+
Grab your besties and treat yourself to the ultimate Galentine’s experience at Mud on Main (423 N Main St)!
Start the day hanging out, snacking, and creating your own custom charcuterie board while enjoying a spread of delicious charcuterie bites. At some point during our time together, we’ll head over to Escape Oshkosh to take on their Sweet Treats Room, a playful, candy-themed escape experience that adds a fun twist to the day. Afterward, we’ll wrap things up back together with more snacks, laughs, and charcuterie time.
Galentine’s Hat Burning At Fire Escape - Friday, February 13
Class Location- Fire Escape, 927 Oregon St, Oshkosh, WI
Class Time- 6pm-9pm, February 13th
Learn how to burn your own hat! All levels of artists welcome- if you’re not comfortable drawing, that’s ok, all you have to do is trace your design!
Start off by listening to an instructor- led tutorial on different ways to burn your hat. Multiple techniques will be demonstrated, from free-hand drawing to transferring a pre-made design template. Finish up at the hat bar where you can choose ribbons and embellishments to create a coordinating hat band!
Valentines Drag Bingo Show (Mature) - Saturday, February 14
The Grand Ballroom at The Howard transforms as Bingo meets Drag. Valentines Drag Bingo Show!
When you come in we will help you find your party’s seats and you and your guests can get settled in and grab some beverages during our cash bar cocktail hour. The queens will start out with performances to get us in Bingo mood! The night will play out with 8 rounds of bingo and more performances.
Valentines Elsewhere
An intimate candle-lit evening designed for lovers, friends, and kindred hearts at Elsewhere Market! Get tickets here.
Each reservation includes a fully-styled Valentine’s table and multi-course evening for you and your guest(s):
- a candle-lit table for tow or four
- personalized Valentine’s card
- one bottle of wine (red, white or champagne
- generous cheese + charcuterie board created by @bar430
- dessert plate to share~
- Dried floral arrangement for table + yours to take home
- 20% off all Market goods
OshFasching 2026 - Saturday, February 14
German Fasching, also known as Karneval or Fastnacht, is a traditional pre-Lenten celebration - and this year we're OshFasching 2026. Come celebrate this tradition with German food, bier, music by Dorf Kapelle, and plenty of Gemutlichkeit at Poplar Creek Barn in Oshkosh!
- 4pm Cocktails
- 5pm Dinner
- 6pm Show
- Feel free to dress in fun or traditional German attire.
Paint by Candlelight - Saturday, February 14
Make a reservation for Fire Escape's Paint by Candlelight and they guarantee a date night experience you will remember forever! Paint any pottery piece on our shelves and create a memory that lasts a lifetime. Reservations are recommended. $10 ticket goes to candy, decor and guaranteed 2 hour reservation.
When Harry Met Sally - Movie at the Time - Saturday, February 14
Rob Reiner directed this among other great movies and in memory of his loss, the Time Theater is donating $1 of each ticket from this special screening to Christine Ann Center. Movie about 7, doors, at 6:30, cash only for everything at the Time!
Enjoy a special Valentine's Day Menu at a local Oshkosh Restaurant:
Have a sweet galentine you'd love to treat? Check out our Galentines Day blog for more things to do and events tailored to you two!
There is SO much to do this Valentine's Day in Oshkosh! Let us know your Valentine’s Day plans!
Stay the night in Oshkosh—click here for overnight options!
