The holidays are around the corner and Oshkosh is ready!! Check below for a list of free activities to do with your friends and family! Let’s get festive people!!!

Free All Season Long!

Support local by completing stops along the Holly Jolly Holiday Trail and win cool prizes!  Learn more.

November 30th- Annual Holiday Tree Lighting and Holiday Parade presented by Oshkosh Corporation! 

Tree Lighting- Kick off the Holiday Parade and holiday season downtown in Opera House Square! Enjoy music in Opera House Square from 5-6 p.m., the Tree Lighting Ceremony at 6 p.m. and the parade beginning at 6:30 p.m.

Parade- Join us as we transform our downtown into a place as magical as the North Pole! The Downtown Oshkosh Holiday Parade presented by Oshkosh Corporation begins at 6:30 pm and this year’s parade theme is “The Nutcracker”!

*Parade route begins at the intersection of N Main and Ceape and heads north until the intersection of N. Main and Irving. 

December 2nd- Christmas in the Air at the EAA Museum

Warm up your holiday spirit at Christmas in the Air! The EAA Aviation Museum welcomes all for this FREE family event on Saturday, December 2, 2023, from 10 a.m. to 3 p.m., presented by Festival Foods.

  • Write letters to Santa
  • Visit the Sweet Shoppe for cookies, cupcakes, and milk
  • Local dance, music, and choral performance groups around the museum

To top it off, you won’t want to miss Santa Claus arriving in a helicopter! While Santa visits don't forget to get your picture taken with him!

Donations of unwrapped toys for Toys for Tots or non-perishable food goods for Father Carr’s Place are greatly appreciated.

EAA Christmas in the Air   EAA Photo/Connor Madison

December 2nd & 3rd- The Howard Holiday Market

The Howard transforms into a winter wonderland. Come enjoy artisan, boutique and artist vendors in the Grand Ballroom. The bar will be open for a cocktail while you shop - cash or cards accepted. The Cafe will be open for signature espresso beverages and other warm drinks. Order breakfast or lunch served up by our Culinary Team and enjoy dining with your group in the Great Hall!

  • 10AM Doors Open
  • 10AM-4PM:
  • Cafe: Coffee, Espresso Beverages & Cocoa | Breakfast and Lunch
  • Grand Ballroom: Vendor Market, Cash Bar, Santa Clause (Saturday Only)
  • Great Hall: Seating for Dining
  • 4PM End

Santa Clause will pay a visit on Saturday from 10AM to 2PM. Each “sit” with Santa is a $5 charge. Santa will have a helper who can take a photo on your phone or camera and we welcome you to take your own photos as well! The backdrop will remain up on Sunday and all guests are welcome to take photos at no charge.

December 9th- Reindeer on the Square

Grab lunch, do a little shopping and stop by Opera House Square to see LIVE reindeer from 3:30-5:30pm. Write letters to Santa, enjoy music by Randy Peterson sponsored by Fox Communities Credit Union as well as a hot cocoa bar sponsored by TDS & NAMI Oshkosh. Learn more here!

December 9th - Elf at The Time Community Theater

Enjoy two showings of Elf for FREE thanks to the Downtown BID!

Raised as an elf, human Buddy travels from the North Pole to New York City to meet his biological father, Walter Hobbs, who never knew Buddy existed and, coincidentally, is in desperate need of some Christmas spirit.

December 9th- Ice Skate with Santa! Family Night at the YMCA

Ice Skate with Santa! Bring the whole family for a night of holiday FUN at the 20th Ave Y on Saturday, December 9!

No pre-registration, FREE for all! You don't need to be a Y member to join in the fun - Community Nights are OPEN TO ALL. Bring the family to swim, play basketball, soccer, enjoy a bounce house, and more!




Oshkosh Celebration of Lights 

From November 24th to December 31st, enjoy the drive-thru light show at the EAA Grounds. This year the Oshkosh Celebration of Lights has 7 FREE Community Nights. EVERYONE enters FREE these nights because of our sponsors generosity! Enjoy the show FREE from 5:30-9pm November 29, December 6, 11, 13, 18, & 20! (A donation of a sealed hygiene item (shampoo, deodorant, soap, etc.) or non-perishable in-date food items appreciated)

New Location: 1858 Neunteufel Ave, Oshkosh, WI 54902

The Nativity Collection at Algoma Boulevard United Methodist Church

Did you know a church in Oshkosh, Wisconsin is home to one of the largest permanently displayed nativity collections in the world? Step into the extensive display room at Algoma Boulevard United Methodist Church and view over a thousand of nativity sets made out of everything from fine porcelain to popsicle sticks! This Nativity Collection is one of a kind and is worth a visit.

Letters to Santa!

Drop off your letters to Santa all holiday season in our mailbox in Opera House Square! Drop your letters off by December 14th for a response from Mrs. Claus and Santa’s elves! Download the letter template and coloring page: here!

Holly Jolly Holiday Pass

Support local by completing stops along the Holly Jolly Holiday Trail and win cool prizes!  Learn more here! 

Check in and redeem discounts at participating locations on the Holly Jolly Holiday trail and win prizes including an Oshkosh sticker, winter beanie (while supplies last), and be entered into an Oshkosh Winter Giveaway! Holly Jolly Holiday Pass available November 24 - December 31st, 2023.


Tag Discover Oshkosh in all your holiday fun on Facebook and Instagram for a chance to be featured!!

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