The holidays are upon us and what better way than to celebrate and make memories with the children in your life!  Check out this list of ideas happening in Oshkosh all season long! 

Nutcracker in the Castle & Sugar Plum Fairy’s Cupcake Cafe' at the Paine Art Center & Gardens

Dates: November 21, 2025–January 5, 2026

The beloved Nutcracker fairy tale returns to the Paine "castle" with a mesmerizing array of sights, sounds, and surprises! This holiday season guests are invited to journey through the settings of the story on self-guided tours. Along the way, the tale will be revealed within each elaborately decorated room of the historic Paine mansion. From the opening party scene to the Land of Sweets and beyond, follow the adventure of Clara and the Nutcracker Prince.

On the first floor, each setting features a large storybook with illustrations that depict a portion of the fairy tale. On the second floor, the rooms portray the home of Clara's family and the workshop of her mysterious godfather, Drosselmeyer, along with a fascinating variety of his finely crafted wooden Nutcrackers.

Be sure to make a stop to the Sugar Plum Fairy's Cupcake Cafe for a yummy treat! Located in the Conservatory at the back of the Paine property.
 

Sugar Plum Fairy Cafe at The Paine

Celebration of Lights - at the EAA Grounds!

Dates: November 28th - December 31st, 2025 from 5:30 - 9 pm

1858 Neunteufel Ave, Oshkosh, WI 54902

The COB attracts over 16,000 vehicles each year filled with family and friends geared up to drive through a million twinkling lights. Take your own car through 1.2 miles of holiday sights and sounds through the beautiful EAA Grounds. This endless trail will engulf you into millions of lights, 100+ trees wrapped in lights, sculptures, and light displays! Hop out of your ride and visit with Santa - available November 28th through December 23rd from 5:30-8:30pm! Make sure to have your children bring their Letter to Santa - plus Christmas Eve, he will be out with his reindeer delivering presents!

Celebration of Lights will be offering a horse-pulled wagon ride experience -- to learn dates and times, or reserve your spot for this enchanting experience by calling (920) 303-9200 or email jodi@discoveroshkosh.com.

EAA Christmas in the Air

Date: Saturday, December 6th from 10 am - 3 pm

Location: EAA Aviation Museum

Celebrate the holidays with EAA’s annual Christmas in the Air, a FREE community and family event for all ages, at the EAA Aviation Museum!

Explore the museum and enjoy all the holiday decorations throughout the exhibits. Enjoy a wide variety of holiday activities:

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

Christmas in the Air at the EAA Aviation Museum in Oshkosh Wisconsin

Other Holiday Events: