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Winter 2022 Special Events

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Winter Events

Oswego Christmas Walk at the Museum

While enjoying the downtown festivities, make your way to the museum for holiday music brought to you by area Junior High choirs. Warm up in the historic Roger Matile Room and stroll through the award-winning museum gallery to complete your visit to this beloved community event.

Little White School Museum
Friday, December 3  |  FREE!

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Oswego Holiday Express

The tradition returns this holiday season! Oswego Holiday Express will leave the Santa Station for the North Pole. All aboard to kiddos, young and old! Put on your pajamas, don your warmest apparel, and head to the top of the world on a magical journey. (KV)

South Point
All Ages

21054 | Dec 9 | Th | 4:30-6:00pm | $20(R)/$30(N)

21056 | Dec 10 | F | 4:30-6:00pm | $20(R)/$30(N)

21057 | Dec 10 | F | 6:00-7:30pm | $20(R)/$30(N)

21064 | Dec 11 | Sa | 2:00-3:30pm | $20(R)/$30(N)

21065 | Dec 11 | Sa | 4:00-5:30pm | $20(R)/$30(N)

21066 | Dec 11 | Sa | 6:00-7:30pm | $20(R)/$30(N)

21067 | Dec 12 | Su | 2:00-3:30pm | $20(R)/$30(N)

21068 | Dec 12 | Su | 4:00-5:30pm | $20(R)/$30(N)

21069 | Dec 12 | Su | 6:00-7:30pm | $20(R)/$30(N)


Gingerbread Drink & Decorate

Take a gingerbread break this holiday season. Leave the kids at home for this adult only evening of candy coated creative exterior decorating. Each registration includes a “holiday spirit” and nibbles from while you work. Fee is per person. Everyone building their own house must register for the Grand Designer fee (which includes Gingerbread house foundation base, icing, and candy décor). Additional guests helping the Grand Designer on the same house should register for the Assisting Designer Fee. Registration deadline is Wednesday, December 8.

Fox Valley Winery
Ages: 21 and up

21142 | Dec 14 | Tu | 6:30-8:30pm | $25(R)/$35(N)
Assistant Designer | $15(R)/$25(N)


Santa on the Line

Christmas is just around the corner, and Santa has set aside some special time to talk with the children of the Oswegoland area! He wants to hear how your child’s year has been, all of their Christmas wishes, and, most of all, to spread Christmas cheer. (CV)

Registration for this event closes on December 9.

All Ages

21154 | Dec 15 | W | 6:00-8:00pm | $5(R)/$6(N)


Happy Noon Year

Ring in the NOON year with this family friendly event where kids of all ages can enjoy New Year’s Eve! Burn off some energy playing in the gym, make a party favor, or grab a snack. This NOON year will be complete with a countdown and balloon drop at noon. Each person attending must register. (ZD)

Boulder Point
All Ages

21757 | Dec 31 | F | 10:00am-12:00pm | $15(R)/$20(N)


FREE! The Great Puzzle Pass

Winter is a great time to break out a 1000 piece puzzle, but what if you’ve already solved that eagle soaring over mountains masterpiece? We’ve set up a January trading post for all puzzle aficionados. Gather up all your old puzzles, confirm they have every piece, and trade them for a new puzzle challenge at The Great Puzzle Pass. Boulder Point’s new lobby will be accepting all your old puzzles from January 3-7. On January 8 you can bring tickets for donated puzzles to the Puzzle Pass. Head home with a new mindbender to work out this winter. (KV)

Boulder Point
All Ages

Drop Off: January 3-7, 8:30am – 4:30pm
Puzzle Pass Pick up: Saturday, January 8, 10:00am – 12:00pm

FREE! Journey Stories Poster Exhibit

The Little White School Museum invites you to a special exhibition exploring how the travel and movement of people has shaped the country. The poster exhibit is brought to you courtesy of the Smithsonian Institution Traveling Exhibition Service.

Little White School Musuem
All Ages

January 3 – February 25

FREE! National Nothing Day

Make an important appointment to do nothing. Clear your calendar and enjoy a day free of obligations or deadlines. Be free and take it easy! (CV)

All Ages

21753 | Jan 16 | Su | 8:00am-8:00pm | Free!


Cabin Fever Frenzy

Ready to shake things up this winter? Face the Cabin Fever Frenzy! Part scavenger hunt, part game night, part creative outlet, the Cabin Fever Frenzy is a 48-hour team based challenge. Teams of 2-6 will be presented with over 100 mini-challenges (like singing a TV theme song, recreating a famous piece of art, or tapping into your pop culture knowledge). This app-based adventure will be held February 4-6. The team with the highest points will receive the $100 grand prize. Additional information and challenge guidelines will be available at Registration is per team and the deadline is January 25. (CV)

All Ages

21723 | Feb 4-5 | F-Sa | 7:00-6:00pm | $30(R)/(N)


Daddies, Dance, and Doughnuts

Little ladies, when you wake up Saturday morning, put on your princess gear and bring your Dad for doughnuts and dancing at the Civic Center! We will be putting on the hits and decorating some tasty treats. You are never too young for a sweet Saturday. This special event is designed for girls 2-5 and their dad. Register by February 1 for $30/ couple and $15/additional child. (ZD)

Civic Center
Age: 2 – 5

21405 | Feb 5 | Sa | 10:30-11:30am | $30(R)/$45(N)
21406 | Feb 5 | Sa | 9:00-10:00am | $30(R)/$45(N)
21407 | Feb 5 | Sa | 12:00-1:00pm | $30(R)/$45(N)


daddy daughter

Daddy Dinner Dance

Dads will be dancing with their stars this February! Girls in their fanciest finery are invited to celebrate their favorite knight in shining armor. Daughters will enjoy a delicious dinner with their dads and then dance the night away. Register by February 1. $25 per additional child. (ZD)

Civic Center
Age: 6 – 11

21408 | Feb 4 | F | 6:30-8:00pm | $50(R)/$65(N)


Mother Son Super Night Out

Moms and sons, show us your super moves this February! Pull out your favorite super hero outfits for our Super Night Out. Enjoy some modern tunes as instructors lead you through popular dances. This special night with your son includes dinner and dessert bar. Register by February 22. $25 per additional child. (ZD)

Civic Center
Age: 2 and up

21417 | Feb 25 | F | 6:00-7:30pm | $50(R)/$65(N)


Mother Son Big Pig Tournament

In driveways all over Oswegoland, sons have been practicing their granny shots and Moms have been getting closer and closer to the perfect double hoop scoop. This double elimination tournament brings a little bit of March Madness to the classic game of clever basketball shots. Mom and her ballers can also win fame and prizes in this year’s dunk contest. Teams must be registered by February 24 to get Big Pig team shirts. The competition is limited to mothers and their boys. Register by your child’s grade. Check in and open shooting start 30 minutes before tourney start. Only the championship games are open for public viewing. $20 per additional child. Registration closes on Tuesday, March 3.(ZD)

Fox Chase Elementary School
All Ages

21278 | Mar 5 | Sa | 5:30-9:30pm | $45(R)/$60(N)


Pop Up Dog Park

Let your best four-legged friend run like the wind at the pop up dog park. Sit and stay with some new friends. Preregistration is encouraged, and price is per dog. Drop in registration will be available the day of the event for $8, space permitting. (CV)

Prairie Point Community Park
All Ages

Large Dog (25 lbs or more)
21718 | Feb 19 | Sa | 10:00am-2:00pm | $5(R)/(N)
21719 | Mar 19 | Sa | 10:00am-2:00pm | $5(R)/(N)

Small Dog (25 lbs or less)
21720 | Feb 19 | Sa | 10:00am-2:00pm | $5(R)/(N)
21722 | Mar 19 | Sa | 10:00am-2:00pm | $5(R)/(N)


Flashlight Egg Hunt

Bring your flashlights and join us for this nighttime hunt for eggs. You’ll also have the chance to win a great prize like a drones, Bluetooth speakers, cameras, and more! Each participant will go home with a candy bag. Please bring a flashlight and prize bag. The hunt will be held rain or moonshine, so be sure to dress for the weather. The first 50 to enter code 2022EGG during registration will receive a special rate of $6. Playground check-in will be 7:15 -7:30pm with a 7:40pm hunt! Registration space is limited and ends on April 11. (ZD)

Wormley Heritage Park
Age: 6 – 15

21415| Apr 14 | TH| 7:30pm| $9(R)/(N)


Saw Wee Kee Trail Run Series

Join the Oswegoland Park District in this new fun and challenging trail run series at the beautiful Saw Wee Kee Park. The soft path, with its twists and turns, ups and downs, makes for a great all natural run whether the weather makes it a muddy mess, or a fragrant wildflower filled dash. Runners are bib-timed and sent in every few minutes. Each race features a different course and different piece of the medal! Attend each of the four runs in the series and complete the 2022 medal! There are no refunds for athletic events. Registration closes February 18th. (ZD)

Saw Wee Kee Park
All Ages

21280 | Feb 26 | Sa | 1:00-5:00pm | $100(R)/(N)


trail run