Pretzel City Winefest-2026
12:00 PM - 4:00 PM
Join us for another great Downtown Freeport event on Saturday, May 10! $25 Event Admission includes a souvenir wine glass and a gift. Pretzel City Winefest is a wine-tasting event in Downtown Freeport featuring Illinois, Wisconsin, and Iowa wines on ...
WEN - Leading in Male Dominated Industry
12:00 PM - 1:00 PM
Join us as Chris Kuberski, Highland Community College's President, reflects on her leadership journey. Chris will be retiring at the end of this academic school year and sharing her wisdom with our group before her departure.
Music on Chicago June 2026
5:00 PM - 10:00 PM
Music on Chicago has been a tradition in Downtown Freeport for over 20 years because of the great music, comradery, and summer-celebration atmosphere it brings! All events take place in Downtown Freeport’s new Art Plaza at the corner of Chicago Avenue ...
Music on Debate
6:30 PM - 8:00 PM
June 25th Kendra Swanson July 9th HCC Big Band with Bill Petersen July 16th Ukelele Express 815 July 30th Lobbin Robbins August 6 (Southpaw Stance August 13 or van funk) August 20 The John Hartman Jazz Alliance
Music on Debate
6:30 PM - 8:00 PM
June 25th Kendra Swanson July 9th HCC Big Band with Bill Petersen July 16th Ukelele Express 815 July 30th Lobbin Robbins August 6 (Southpaw Stance August 13 or van funk) August 20 The John Hartman Jazz Alliance
Music on Debate
6:30 PM - 8:00 PM
June 25th Kendra Swanson July 9th HCC Big Band with Bill Petersen July 16th Ukelele Express 815 July 30th Lobbin Robbins August 6 (Southpaw Stance August 13 or van funk) August 20 The John Hartman Jazz Alliance
Music on Debate
6:30 PM - 8:00 PM
June 25th Kendra Swanson July 9th HCC Big Band with Bill Petersen July 16th Ukelele Express 815 July 30th Lobbin Robbins August 6 (Southpaw Stance August 13 or van funk) August 20 The John Hartman Jazz Alliance
Music on Chicago with Boogie and the The Pork Tornadoes with special guest DJ Cup
5:00 PM - 10:00 PM
Music on Chicago this August will feature The Pork Tornadoes with special guest DJ Cup. Gates open at 5:30. There is a $5 entry donation. Children 5 and under are free.Bring your lawn chair and get ready for a good time!!
Music on Debate
6:30 PM - 8:00 PM
June 25th Kendra Swanson July 9th HCC Big Band with Bill Petersen July 16th Ukelele Express 815 July 30th Lobbin Robbins August 6 (Southpaw Stance August 13 or van funk) August 20 The John Hartman Jazz Alliance
Pretzel City Brewfest 2026
1:00 PM - 5:00 PM
Pretzel City Brewfest will take place on Saturday, September 27th in downtown Freeport. This is a 21 and older & rain or shine event. Tickets can be purchased with credit/debit cards online. VIP will open at noon with General Admission opening at 1 pm ...
Wine & Witches 2026
4:00 PM - 9:00 PM
Wine & Witches October 9 4:00 PM - 8:00 PM Downtown Freeport Join us for another free Downtown Freeport event on Thursday, October 10 ! While general admission is free, we’re offering an exclusive VIP experience for just $20 , ...
Mistletoe Walk
12:00 PM - 5:00 PM
Get ready for a jolly weekend full of holiday cheer and shopping! Join us for the Mistletoe Walk in Downtown Freeport and kick off the holiday season by exploring our local shops, filled with unique gifts and festive deals. From noon to 4 pm, enjoy the ...