Published by kelly on February 20, 2026
What is Winterfest?
Winterfest is an annual community-wide celebration for all things winter in Stillwater.
The mission of Stillwater Winterfest is to engage the Stillwater community and visitors to our area in a vast array of events and opportunities in the mid-winter season!
There are so many ways to enjoy this long weekend of fun in Stillwater we are dedicating a newsletter to it! Here are some dates, details and information you will need to enjoy Winterfest in Stillwater this year!
FRIDAY, FEBRUARY 20, 2026
4:00pm – Opening Ceremonies at JX featuring live music with Anglo & Collins
6:30pm – Class Picture at JX – get in the photo and receive a free drink!
7:00pm – Fireworks viewing from Papa’s Rooftop & River Siren Brewery
8:30pm – Midnight – Live Music from Drink 182 and Some Sh!tty Cover Band
SATURDAY, FEBRUARY 21, 2026
10:00am-1:00pm – Kids & Family Fair at Loft 214
12:00-3:00pm – Bags Tournament at JX Venue
12:00-8:00pm – Food trucks outside JX Venue
4:00pm – Bar Crawl Kickoff at JX Venue
4:00-6:00pm – Live Music by Prank Williams
5:00pm – Casserole Cookoff & Saturday Sipper at JX Venue
6:30pm-Midnight – Live Music by Atari & Good for Gary
*Photo by Pictures Over Stillwater
SUNDAY, FEBRUARY 22, 2026
Puppies & Pumps – Drag Brunch + Purse Bingo!
11:00am – Door Open
12:00pm – Event Begins
MONDAY, FEBRUARY 23, 2026
5pm – Service Industry Night at JX Venue, featuring the
2026 BEST BARTENDER IN THE VALLEY Cocktail Competition.
It’s a night of incredible talent, creative cocktails, and celebrating the
heart of the service industry.
5:00pm: Doors Open, Welcome Drink, Social Hour
6:00pm: Competition Starts – Best Bartender in the Valley
9:00pm: Event Ends
Stillwater Winterfest Pub Crawl & Shop Local
Explore Stillwater and win big! Mention Winterfest and discover specials and discounts at participating locations! Visit any of the participating locations listed HERE during Winterfest and scan the Winterfest QR punch at each stop. Each scan earns you one punch, and the more stops you visit, the more entries you’ll receive for prizes up to $1,000! Happy exploring!
FREE! With the exception of brunch and Bingo, it’s all free to attend!
See the map below to help you navigate all of the festivities!
Here are some helpful links as your book your visit to Stillwater!
Find your lodging options HERE.
More Things to Do HERE.
Dining and Nightlife HERE
Shopping HERE.
We look forward to hosting you in our beautiful town!
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