Uniquely Oregon in October


“I’m so glad I live in a world where there are Octobers.” ― L.M. Montgomery, Anne of Green Gables

Whether you are trying to find Halloween fun for the whole family (including the pupper) or looking for a date night out, we have plenty of options for you to choose from! Enjoy the fleeting warm weather by bringing the whole family to The Oregon Park District’s Howl’oween festivities and enter your dog in their annual costume contest. Or, plan a parents-only mini-getaway by enjoying craft beer and specialty wine at The Experience for Autumn on the Vine. The fun only begins there. Continue your search for more activities below!




Pegasus Special Riders Annual Horseshoe Ball

October 1, 2017 3:30pm – 7:30pm Barnocopia, Polo IL

Purchase your tickets today to enjoy a prime rib dinner to support Pegasus Special Riders, Inc., a therapeutic horseback riding facility operating for the sole purpose of helping those with special needs. Food will be catered by Pinecricker Cafe in Polo and entertainment by Magician Adam Sean. Also, check out and bid on live and silent auction items.  Tickets $60/person Please call 815-973-3177 for tickets and further details.



Murder Mystery Dinner @ Stronghold Castle

October 1, 2017 Doors open at 1:30 pm, Show Time & Appetizers 2:00pm

Come join the fun with live interactive theater at the Stronghold Castle, where you are a part of the show! It is 1929 and Mr. Walter Strong and his wife Josephine host a glamorous dinner party at their new summer home, Stronghold Castle. However, a mysterious murder shocks the evening and guests become suspects! Guests are encouraged, but not required, to dress in their best 1920’s attire. $60 per ticket/$300 Table of 6. http://www.oregonil.com/component/jevents/icalrepeat.detail/2017/10/01/1142/-/murder-mystery-dinner-theater?Itemid=1


Autumn on the Vine

October 7, 2017 5:00-8:00pm @ “The Experience”    305 W. Washington St. Oregon, IL

Enjoy craft beer, specialty wine, martini tastings, and local artisan appetizers. Advanced tickets are limited and include more beverage and appetizer opportunities.  On sale now at the following locations: Conover Coffees & Chocolates, JTI Salon & Spa, Merlin’s Greenhouse & Flowers, and the Oregon Chamber Office. Call ahead to reserve yours today! 815-732-2100 P.S. This will be a “first peek” at Merlin & Cindy Hagemann’s newest business venture!




Autumn on Parade

Saturday/Sunday:  October 7-8, 2017      Downtown Oregon

We hope you’ll join us to the 47th anniversary of the Autumn on Parade festival! This year’s theme is “Music:  Then and Now“. The heart of Autumn on Parade is its Farmer’s Market and Craft Fair, located on the historic Ogle County Courthouse Square in downtown Oregon where more than 175+ craft booths surround the 125-year-old Ogle County Courthouse. Not a crafter? Don’t despair…there is something for everyone. The Fun Zone, located just north of the Courthouse Square, offers a place for kids to burn off some energy. And, if the whole family is looking to get some exercise, they can participate in the 5K race/1 mile fun run on Sunday morning. Northern Illinois’ largest parade follows on Sunday – with over 150 units from around the region and Chicago.   This is only the beginning of what the weekend has to offer. For more information and a schedule of events, please click HERE.


Olde English Faire on the Castle grounds @ Stronghold

October 7th & 8th, 2017    9:00am – 5:30pm each day

During the first weekend in October, Stronghold transforms itself from a modern retreat and meeting facility to the site of the Olde English Faire. Wandering players perform both onstage and off as crafters and merchants display their wares. Minstrels fill the pathways and stages with melodies while children gather in the Gremlin’s Garden for stories and other children’s activities. These and many more delights await you at the Olde English Faire!

Purchase a 2 day admission online for the same cost of a one day ticket at the gate by clicking here



Foundation for Focus House Car Show

October 7, 2017      8:00am-3:00pm Trophies at 2:00pm

Whether you are looking to enter your ride, view the classic cars, or just support a great cause, you are sure to have a great day at the Annual Focus House Car Show. And, don’t forget about the 50/50 raffle and shuttle to the Autumn on Parade Craft Show. All proceeds from the Car Show are contributed to the Foundation for Focus House, a residential facility that serves adjudicated youth in our area.  Breakfast and lunch will be served on site and food sales will benefit the Chana School Museum.



Third Sunday Strum-along Sponsored by the Ukulele Station America

October 15, 2017      7:00 pm-8:30 pm     @ Alfano’s – 801 S. 4th St. Oregon, IL

Grab your ukulele and join us as we sing and strum at Alfano’s Restaurant. Come early and enjoy drinks and delicious food before we play. Be sure to bring your songbook: “The Daily Ukulele – Leap Year Edition” For more information, contact John at (815) 994-1246.

Ukelele Station America (USA)



Halloween on the Prairie

October 19, 2017 12:00pm-4:00pm     Byron Forest Preserve

Join The Byron Park District for a “Spooktacular” afternoon of Halloween themed fun! Enjoy a tasty treat or take relaxing hayride through the gorgeous prairies of the Byron Forest Preserve. There will be children’s games, face painting, and much more. This is one event that everyone in the family will enjoy! Admission is free. Games are .25 each or 5 for $1.00

The Byron Forest Preserve has the newest and largest (4,000 sq. ft.) interpretive prairie displays in Northern Illinois.   See the land as it was in the 18th Century and before…


6th Annual Howl’oween Canine Costume Contest

                Sponsored by the Oregon Park District

October 24, 2017 5:30pm-7:00pm

Free Admission Wiggly Field at Veterans Park just off 10th St.

Bring your pooch for the doggie parade at 5:30pm dressed in their Halloween costume. Judging will follow with awards to the winning canines and a Howl’oween treat for all participating pooches. Categories for judging include: Best Purchased Costume, Best Homemade Costume, and Best Group. Get your photo taken with your pooch at the Haunted Howl’oween Cemetery to commemorate the fun evening. All dogs must have a permit and all park rules and regulations apply.





The Village Bakery Cooking Class

October 28, 2017            9:00am-11:00am           Adult & PreK-K

Join the Village Bakery and their talented staff during the holiday season for an exciting baking experience. This is a family oriented program. Each participant should be accompanied by a parent or grandparent. Bring your pre-K-K child/grandchild in costume for an opportunity to bake tasty, take home Halloween treats! Contact the 815-732-3101 for more information and to register. Deadline to register is 10/22/17. Cost: $10 Residents/$12 Non-residents.