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Fall 2022 Special Events

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Fall Events

Oswego Country Market

Every Sunday, June through September, downtown Oswego opens up for the Oswego Country Market. This fresh air market is the best place to shop each week for locally grown produce, fresh farm eggs, raw honey, delicious Wisconsin cheese, and fresh baked bread. While spending time downtown, stop to visit the many stores open during the Oswego Country Market. View the list of vendors.

Main Street, Downtown Oswego

Sundays, June 5-September 25 | 9:00am-1:00pm

Monday Miles

Monday Miles is free to all participants this year. Monday Miles will be a fun way to be active by running or walking 1, 2, or 3 miles each Monday evening from 6/7-8/9. Come to seven or more Mondays and earn a commemorative 2021 event t-shirt. Work all summer and set your goal for the final week’s bib-timed run! 6:00-6:30pm! Course will be open until 7:30pm (ZD)

Prairie Point Community Park

Jun 6-Aug 15 | M | 6:00-7:30pm | Free

Puddle Jumpers Morning

They’ve spent the summer having fun in the sun; now let your little ones flirt with the dirt! Come with your end of the season sand and water toys and let your preschooler explore, play, dig, roll, splash and jump all without a single call to “stay out of the dirt!” Parents stay to play with their puddle jumper free of charge, older siblings must wait until Pig Pen Afternoon to play. Kids and parents should wear clothes and shoes that can be disposed of, and have protection for car seats on the way home. The first 25 to register receive a special rate of $6 while using the discount code 2022Puddle. Pre-register today for $9 or come that morning with your $12 and be ready to roll – in the mud! Pre-registration ends August 11. (ZD)

Prairie Point Community Park
Age: 2 – 5

22366 | Aug 13 | Sa | 10:00-11:30am | $9(R)/(N)


Pig Pen Afternoon

There’s never been a muddier time to make a pig of yourself! Slop to the top of the Pig Pen hill, slide down the slimiest muck at the Pig Pen Afternoon. Your oldest stained clothes and shoes, along with goggles are recommended. The first 25 to register receive a special rate of $6 while using the discount code 2022PigPen. Pre-register today for $9 or come that afternoon with your $12 and be ready to roll – in the mud! Pre-registration ends August 11. (ZD)

Prairie Point Community Park
Age: 6 – 11

22365 | Aug 13 | Sa | 12:30-2:00pm | $9(R)/(N)


NEW! – Fall Carnival

Labor Day Weekend will bring the Windy City Carnival back to town. Close out your summer with one last thrill ride. The midway and all the rides will be coming to Prairie Point Community Park to cap off your summer season.

Prairie Point Community Park

Friday, September 2  ||  5-9pm
Saturday, September 3  ||  1-10pm
Sunday, September 4  ||  1-8pm


Oswego Brew at the Bridge

Fall means Oswego Brew at the Bridge in Hudson Crossing Park. The best Illinois breweries are showcased on a beautiful day in the park. Home Brew hobbyists offer their latest delicious experiments, great food vendors tempt your tummy, and the riverfront park is filled with great music. Participants begin with a $25 Starter Pack that include your age-verified wristband, commemorative Oswego Brew tasting vessel, and five 2 oz taster tickets. There will also be three Home Brew samples available to guests from noon – 4:00pm or until supplies last. Our Early Access Pass for $35 allows you access to Oswego Brew one hour earlier at noon. Those guests purchasing online will have the Early Access Pass for free. New in 2022, choose your glass! Guests have an option of a 5 oz sampler glass to use with one 2 oz. taster ticket or 10 oz. acrylic cup for a four-ticket 8 oz pour. Tickets are available online beginning September 8. (KV)

Hudson Crossing Park
All Ages

Saturday, September 17
1:00–7:00pm (Noon for Early Bird)


Pint 1K Run

Race to the taste! This run puts athletes to the test in a grueling .1 kilometer course (.0621 miles). Athletes who register by Wednesday, September 7 will be guaranteed a t-shirt, bib, & .1K sticker. Brew at the Bridge entry can be purchased separately. Race fee is $15 and Brew at the Bridge access can be purchased for an additional $25. Athletes will receive free early access to the event. This is a non-timed race. Registration closes Wednesday, September 7. There are no refunds for special events. (ZD)

Ages 21+

23549 | Sep 17 | Sa | 11:55am-12:10pm | $15(R)/(N)


Home Brew Contest Entry

We are hosting a Home Brew Contest that will be held on Friday, September 16. Any home brewers (whether they are affiliated with a club or not) are invited to submit their brews for feedback from a panel of pro brewers and experienced judges. Visit for full contest details. (CV)

Age: 21 and up

23383 | Sep 16 | F | 3:00-6:00pm | $6(R)/(N)


Kids Triathlon

Kids are filled with the energy to swim, bike, and run to the finish line. Coordinated in partnership with the School District’s Physical Education teachers, 3rd through 8th graders compete in this non-continuously timed event consisting of a 100m swim, a 3 mile bike ride, and a ½ mile run (7/8 graders will run 1 mile). While awards are given to the fastest in each division, the real winners are all the spirited students who bolt from the start and head towards every finish. Everyone receives a t-shirt and finisher medal. Park District athletic events are non-refundable. Registration deadline is September 15. (ZD)

Oswego East High School

Sun, Sep 25  |  9:00am

Individual (Grades 3-8)
Through August 31: $25
September 1 – September 15: $30

Team (Grades 3-6)
Through August 31: $75
September 1 – September 15: $90


Saw Wee Kee Trail Run

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 different courses and different gear! Attend each race and receive a piece to the 2022 medal!

Saw Wee Kee
Age: 12 and up

Oct 22 | Sa | 2:00pm | $30(R)/(N)


fishing with dad

Fishing with Dad

Enjoy an October Saturday in the park with your Pops! Kids, bring your dad as we try our hand at fishing, cook a delicious outdoor breakfast, and spend a terrific morning together. Oswego’s Fishin’ Fools club will supply the poles, bait, and assistance. If you register by Thursday, September 15 we will have a cozy sweatshirt for each fisherman! Class fee is per person; everyone must register. (ZD)

Chesterfield Park
All Ages

23430 | Oct 1 | Sa | 9:00-11:00am | $25(R)/$40(N)


Adult Dodgeball Tournament

Dodge, Dip, Duck and Dive your way to victory. Bring out your team. Games will be played 6 vs. 6, with a maximum of 10 per team. Tournament format will be determined based on the number of teams. Matches will be best of three games. There are no refunds for athletic events. Registration ends 9/27. (ZD)

Murphy Jr. High School
Age: 18 and up

23366 | Oct 1 | Sa | 4:00-6:00pm | $75(R)/(N)


High School Dodgeball Tournament

Dodge, Dip, Duck and Dive your way to victory. Bring out your team. Games will be played 6 vs. 6, with a maximum of 10 per team. Tournament format will be determined based on the number of teams. Matches will be best of three games. There are no refunds for athletic events. Registration ends 9/28. (ZD)

Murphy Jr. High School
Age: 14 – 17

23370 | Oct 1 | Sa | 4:00-6:00pm | $75(R)/(N)


Oswego Cemetery Walk

Experience local history come to life during our annual Oswego Cemetery Walk. Participants will be guided through the cemetery to visit with”ghosts” of early Oswego residents and pioneers. Pre-registration is required as there are multiple start times. Participants should be able to walk for 45 minutes, wear comfortable shoes, and are encouraged to bring a flashlight. An adult must accompany all children. Registration is per person. Presented in partnership with the Oswegoland Heritage Association. (AJ)

Oswego Cemetery
All Ages

Thursday, October 6
Sessions 5:00pm through 8:20pm


Pawcasso – Paint with Your Pet

Bring your best four legged-friend out to the park for an evening of arfs and crafts! You and your canine will work together to create paw print note cards and abstract canvas art. All dogs must remain on leash during the event. All craft mutt-erials will be available to “grab and go” with instructions in case your artist isn’t in the mood. Registration fee is per “artist” or set of materials. (CV)

Hudson Crossing Park
All Ages

23453 | Oct 11 | T | 6:00-7:00pm | $15(R)/$19(N)


Halloween House Decorating Contest

Whether you like tricks or treats, we want to see your best Halloween House Decorating this fall. Register by 10/23 for your house to be included in the contest. Oswegoland Park District staff will visit each home between 6-9pm on 10/25 to evaluate and take Decorators will need to pictures of the decor that will be posted on Facebook. The two Hallo-winners will be the Most Spooktacular (as evaluated on by staff) and the People’s Choice (voted for via Facebook until 10/27). Winners will be announced on 10/28 and will receive a yard sign and gift card. Maps to all participating homes will be provided online for families to take a drive to see them in person. This contest is open to residents only. (CV)

All Ages

23384 | Oct 25 | T | 6:00-9:00pm | Resident: $5


Monster Mash Bash

There’s a frightening amount of things to do at this year’s Bash! Crafts, candy games and more wear your Halloween costume, and join the fun at Oswego High School. New this year, pre-register for $5 or pay $8 at the door. Registration is per child. Adults are free. Registration closes Thursday, October 27. (ZD)

Oswego High School
All Ages

23375 | Oct 29 | Sa | 2:00-4:00pm | $5(R)/(N)


Oswegoland Barrel Nights

Barrel Nights is back on the greens of the Fox Bend Golf Course. This autumn’s line up features Whiskey and small plates. Savor five unique whiskeys paired with amuse-bouche bites, all that can be enjoyed locally. Enjoy a beautiful night in the outdoor pavilion. Sip something that warms you matched with flavors that will fill you. Reserve your spot today.

Fox Bend Golf Course
Age: 21 and up

23325 | Nov 3 | Th | 7:00-8:00pm | $35(R)/$50(N)


Jack-o-Lantern Recycling

Go green after Halloween and drop your carved pumpkins off at Prairie Point Park between 3-5pm. These gourds will be sent sailing through the skies during the Rage Cage event that evening, then spread in the Community Gardens to fertilize the ground for next season’s plants. Only carved, seed free pumpkins will be accepted. Free and easy way to have your pumpkin give back! (CV)

Prairie Point Community Park
All Ages

Nov 4 | F | 3:00-5:00pm | Free


Dine n’ Smash – Food Trucks & Rage Cage

Grab dinner from a popular food truck and have a blast as you let loose at different Rage Cage smash stations including a pumpkin smash, car bash (thanks to City Auto Wreckers), & BYOTrash open range rage cage.$5 buys you three swings at smashing a pumpkin, throwing a plate, or taking a whack at a car. All smashers must wear long sleeved shirts, full pants, closed toed shoes, and protective gear provided at the event. Register before November 3 for smashing savings. Pre-registration lets you rage at three stations for only $10. Register onsite for $5/Rage Cage station. Cash or Cards accepted. (CV)

Prairie Point Community Park
Age: 10 – 89

23427 | Nov 4 | F | 5:00-7:00pm | $10(R)/$20(N)


Gobbler Hobbler Mashed Potato Mile

Enjoy a one mile jog or run just for fun! Our Mashed Potato Mile begins and ends at the Fox Chase Elementary School. All preregistered runners are guaranteed a hoodie sweatshirt, refreshments, and finisher’s ribbon. Athletes are invited to enjoy complimentary walking pancakes after the run. There are no refunds for athletic events. Race day registration ($29) begins on Sunday, November 11 at 7:30am! (ZD)

Fox Chase Elementary School
All Ages

23368 | Nov 13 | Su | 8:30-11:00am | $30(R)/(N)


Gobbler Hobbler 10K Run

Celebrate Fall with a scenic 10K run down the Fox River and through beautiful downtown Oswego! The chip-timed course begins and ends at Fox Chase Elementary School. Volunteers provide two water stations on the course. All pre-registered runners are guaranteed a hoodie sweatshirt, refreshments, and finisher’s medal. Athletes are invited to enjoy Gobbler Hobbler’s famous complimentary walking pancakes after the run. Registration closes 11/4. There are no refunds for athletic events.

Fox Chase Elementary School
All Ages

23367 | Nov 13 | Su | 8:30-11:00am | $55(R)/(N)


Oswego Holiday Express

The tradition returns this holiday season! Oswego Holiday Express will leave the Santa Station (South Point, 810 Preston Lane, Oswego) for the North Pole the weekend of December 9 -11. 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. Mrs. Claus will greet you, you’ll enjoy hot cocoa from the Village Grind and meet Santa! Each participant, from Grandma to the baby, must be registered. Trains depart every 20 minutes throughout your registered session. Refunds accepted until December 5. Non-resident registration begins November 1. Wheelchair-accessible trains will only be available on Friday evening. (KV)

South Point
All Ages

23326 | Dec 9 | F | 4:30-6:00pm | $25(R)/$35(N)
23327 | Dec 9 | F | 6:00-7:30pm | $25(R)/$35(N)
23329 | Dec 10 | Sa | 4:00-5:30pm | $25(R)/$35(N)
23330 | Dec 10 | Sa | 6:00-7:30pm | $25(R)/$35(N)
23346 | Dec 10 | Sa | 2:00-4:00pm | $25(R)/$35(N)
23331 | Dec 11 | Su | 2:00-3:30pm | $25(R)/$35(N)
23337 | Dec 11 | Su | 4:00-5:30pm | $25(R)/$35(N)
23345 | Dec 11 | Su | 6:00-7:30pm | $25(R)/$35(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” from the Fox Valley Winery and nibbles while you work. Fee is per person and includes a gingerbread house and decorations. Registration deadline is Wednesday, December 7. (CV)

Fox Valley Winery
Age: 21 and up

23382 | Dec 13 | T | 6:30-8:30pm | $29(R)/$39(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. If your child would like to hear from Santa, all you have to do is fill out the quick survey that will be emailed to you after registering for this special event. Santa will give you a ring between 6:00-8:00pm on Wednesday, December 14. Registration for this event closes on December 8. Confirmation emails with the survey will be emailed out on December 9. Surveys must be completed no later than December 12, or you will not receive your call. (CV)

All Ages

23426 | Dec 14 | 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

23369 | Dec 31 | Sa | 10:00am-12:00pm | $15(R)/$25(N)