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Fall 2021 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.  (CV)

Main Street, Oswego
Sundays through September 26 | 9:00am-1:00pm  |  FREE!

More Information

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. Registration deadline is September 16. (ZD)

Oswego East High School
Grade: 3 – 8

Sep 26 | Su | 9:00am-1:00pm | $25/individual – $75/team


Lap Swim Practice for Kids Triathlon

Practice your swimming in the Oswego East pool prior to the event. Triathletes will be swimming two laps or four lengths of the pool. Working on your preferred stroke and becoming familiar with the water is the best way to work out any nerves before Triathlon Day.

Oswego East High School
Ages: 7-11

20678 | Sep 12 | Su | 3:00-5:00pm | $6(R)/(N)

20679 | Sep 19 | Su | 3:00-5:00pm | $6(R)/(N)


Saw Wee Kee Fall Trail Run

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. Registration closes Thursday, October 14.

Saw Wee Kee Park
Age: 12 and up

Oct 23 | Sa | 2:00pm | $25(R)/(N)


Oswego Brew at the Bridge

Brew is Back. Let’s spend a day listening to great music, savoring delicious food, and tasting the best beer in Chicagoland. For $25 take your souvenir Oswego Brew glass to one of 20 Illinois craft breweries and enjoy five 2 oz samples of their best offerings. We’re inviting 4 Home Brew companies to give 3 samples of their experiments as well until 4pm. Skip the lines and buy an Early Bird pass at noon for $10 more. Pre-purchasing is not required. Sales begin October 9 at Hudson Crossing Park.

Hudson Crossing Park

Oct 9 | Sa | 1:00-7:00pm (noon start for early bird)

More Information

Home Brew Contest Entry

Home brewers (whether they are affiliated with a club or not) are invited to submit their brews for feedback from a panels of pro brewers and experienced judges. Visit for full contest details. (CV)

Oswego Brewing Co.
Age: 21 and up

21140 | Oct 8 | F | 3:00-6:00pm | $6(R)/(N)


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 28. (ZD)

Oswego High School
All Ages

20680 | Oct 30 | 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

21172 | Nov 4 | Th | 7:00-8:00pm | $35(R)/$50(N)


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 16 we will have a cozy sweatshirt for each fisherman! Class fee is per person; everyone must register. (ZD)

Chesterfield Park
All Ages

20674 | Oct 2 | Sa | 9:00-11:00am | $25(R)/$40(N)


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
Saturday, October 2 | $75 per team

20691 | Junior High | 2:00-4:00pm

20690 | High School | 4:00-6:00pm

20681 | Adult | 6:00-8:00pm


Oswego Cemetery Walk

In partnership with the Oswegoland Heritage Association, we invite you to experience community history through the stories of those who have called our area home during the 20th Oswego Cemetery Walk. Participants will be guided through the cemetery to visit with the ghosts of early Oswego residents and pioneers. Pre-registration required. Be assured one of limited spots by registering early for this historic event! (CH)

Oswego Township Cemetery
All Ages

Oct 7 | Th | 5:00-9:00pm Start Times | $5(R)/(N)


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Park After Dark: Camp Where-We-Go

For years, campers at Camp Where-We-Go have heard tales of the creature that roams the woods, howling, snarling, and hunting down unsuspecting victims. Each year, the brave and bold venture into the woods under a full moon. Some never make it out at all. Bring a flashlight to help guide you during this interactive adventure. Dare to face the challenge solo, or assemble your best camp crew to increase your odds of making it out unscathed. This scary event is rated PG-13 (for blood, gore, darkness). Upon emerging from the woods, all participants receive gear commemorating their legendary camp experience. (CV)

Civic Center
Ages: 12 and up

21144 | Oct 16 | Sa | 5:30-6:30pm | $20(R)/$25(N)

Ages: 14 and up

21146 | Oct 16 | Sa | 6:30-7:30pm | $20(R)/$25(N)

21147 | Oct 16 | Sa | 7:30-8:30pm | $20(R)/$25(N)

21148 | Oct 16 | Sa | 8:30-9:30pm | $20(R)/$25(N)

After Oct 1 – $20(R)/$25(N)  |  Day of Registration – $30(R)/$35(N)


Help Us Haunt

Become a part of the Haunt Team and help us transform the woods into a werewolf infested camp. We need outgoing and fearless folks to get ghoulish and help us give Oswego a scare. Haunt Team members will need to provide their own costumes, with guidance from event staff. To help you prepare, you will need to attend the Haunt Team 101 Training Camps on Monday, October 11 at 7:00pm at Prairie Point. All haunters will receive event gear and be fed pizza at the end of the night. (CV)

Civic Center
Ages: 14 and up

21152 | Oct 16 | Sa | 4:30-10:00pm | $5(R)/(N)


Halloween House Decorating Contest

Whether you like tricks or treats, we want to see your best Halloween House Decorating this fall. Register by 10/20 to be included. Park District staff will visit each home between 6-9pm on 10/21 to evaluate and take pictures of the decor that will be posted on Facebook.

All Ages

21143 | Oct 21 | Th | 6:00-9:00pm | $5 Residents Only


Remembering Our Veterans

Discover the history of Oswego’s fighting men and women through an extensive display of rarely seen military artifacts selected from the museum’s permanent collection, including items used during the Civil War, World Wars I and II, the Korean Conflict, the Vietnam War, Iraq, and Afghanistan.

Little White School Museum
All Ages

Nov 10-28 | Open Daily During Regular Museum Hours  |  FREE!

More Information

Jack-o-Lantern Recycling

Go green after Halloween and drop your carved pumpkins. 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. (CV)

Prairie Point Community Park

21185 | Nov 5 | 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 trashing an old TV. Participants can also BYOTrash, and smash that in protected areas. Register before November 4 for smashing savings. Pre-registration lets you rage at three stations for only $10. Register onsite for $5/Rage Cage station.

Prairie Point Community Park
Ages: 10-18

21184 | Nov 5 | F | 5:00-7:00pm | $10(R)/$20(N)


Gobbler Hobbler 10K Run & Mashed Potato Mile

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.

Fox Chase Elementary School

Gobbler Hobbler 10K
$35 through July 31
$40 August 1 – September 7
$45 September 8 – November 4
Race Day Registration: $55

Mashed Potato Mile
$30 through November 4
Race Day Registration: $35


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 Pearce’s while you work. (CV)

Fox Bend Golf Course
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)

All Ages

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