Oswego Downtown Association
Cart 0

A downtown with a focus on local artistry and community spirit, Downtown Oswego has many shops, services, and activities for you to enjoy. Whether you visit us to explore our specialty shopping, take advantage of centrally-located services, or attend one of the several seasonal events that take place throughout the year, visiting our downtown will always be an exceptional experience.


Oswego Christmas Walk and
Downtown Cookie Walk
Friday, November 30th 5:00-8:30pm AND
Saturday, December 1st 10:00am-4:00pm

Celebrate the holiday season by visiting downtown for unique treats, fun family activities, and many other special events! The annual Oswego Christmas Walk on Friday, November 30th is being brought to you by the Village of Oswego along with the Oswego Downtown Association, the Oswegoland Park District, the Oswego Chamber of Commerce, the Oswego Library District, and many other local organizations and businesses. Come back on Saturday, December 1st to celebrate Hometown-style as Downtown Oswego’s Main Street becomes Bedford Falls at “It’s A Wonderful Life” from 10am-4pm. Shop local merchants for gifts while enjoying festive music and decorations of a gone-by era. Make your way to “City Hall” (a.k.a. Oswego Cyclery) to celebrate the final scene of the beloved movie by bringing your donations of non-perishable food or cash to remember those in need this holiday season (donations will be provided to the Kendall County Food Pantry).

The much-loved Oswego Downtown Cookie Walk will take place during “It’s A Wonderful Life” on Saturday, December 1st. Purchase a tin for $10 and visit your favorite stores on the “walk” to fill your tin with homemade holiday treats provided by our local downtown businesses. Tins may be purchased for $10 each after November 19th on Main Street at Floral Expressions/Lil Emm’s Boutique, Hudson Design House, and Kimberly Ann’s Boutique.


Memorial Day Parade :  Monday, May 28
Country Market:  Sundays June 3-September 30   9am-1pm
Bentley’s Block Pawty:  Sunday, June 11  10am- 3pm
PrairieFest Parade:  Sunday, June 17  1pm
Beats and Eats:  Saturday, July 28   5pm-10pm
Beats and Eats:  Saturday, August 25   5pm-10pm
Fall Fox Fest*:  Sunday, October 14   9am-4pm
Shop Small Saturday*:  Saturday, November 24   9am-4pm
Christmas Walk:  Friday, November 30 and Saturday, December 1
Downtown Bunny Hop*: Date TBA

*denotes Downtown Association Signature Events



We'd love to invite you to be a part of our next big event! 

If you are interested, simply fill out all the required information within this featured application to let us know what times you'd like to volunteer and what would you like to do during this event. 

We're so excited to have you join our volunteer team! Thank you in advance for your dedication and service to our Oswego Downtown Association.