Events
Freeport and Stephenson County host numerous events each year to enliven the spirt of the area, showcase our greatest attractions and welcome visitors to experience the best of our region.
Upcoming Annual Events
Pretzel City Winefest – May 10, 2025
Wine enthusiasts from around the region flock to Downtown Freeport to enjoy great shopping, food and, of course, wine at Pretzel City Winefest!
Wineries and wine retailers from around the region are showcased at participating storefronts in Downtown Freeport where attendees can walk around and try their favorite varieties while shopping a variety of locations they may miss on a normal trip to downtown. Pretzel City Winefest is hosted by the Greater Freeport Partnership to attract residents and visitors to downtown businesses and showcase the wonderful shops and restaurants Freeport offers.
A $35 general admission ticket includes souvenir tasting glass, wine bag and tasting hours noon – 4 pm. We will also provide you with a booklet and map of the 16 participating locations in Downtown Freeport!
Music on Chicago – June 6, July 3, August 1
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 and Douglas Street. The grounds are ideal for a social gathering with friends or bring the family and blankets to take your spot on the lawn.
This year’s entertainment includes:
June 6 – Fortunate Sons
July 3 (Thursday) – The Real Deal feat. Synergy Band
August 1 – Boogie & the Yo-Yoz w/DJ Cup
$5 admission includes access to the summer’s best party and entertainment by amazing musical acts. Local food vendors are available for dinner options and volunteers serve alcoholic and non-alcoholic beverages during the event. Come join the fun in 2025!
Pretzel City Brewfest – September 27, 2025
The BEST EVENT in ILLINOIS is back! Bring your friends and enjoy the best beer-tasting event in the region! Sample beers direct from the breweries of the area in a lively event format featuring food trucks and competitive games. This is a 21 and older event that takes place rain or shine.
Participants can purchase $40 general admission ticket online which includes entry, 20 tasting tickets, and a souvenir glass. There will be a limited number of $75 VIP passes also available, which include one-hour early entry, 30 tasting tickets, access to special releases, a Brewfest t-shirt, a special VIP souvenir glass, swag bag, and VIP lounge.
Tickets can be purchased in advance with credit/debit card online. Tickets will also be available at the gate for $40 for general admission the day of the event, VIP will not be sold the day of the event. Designated driver tickets can be purchased the day of the event at the gate for $10.
All of this year’s Brewfest information can be found on the Greater Freeport Partnership mobile app. Download it for free on Google Play Store or Apple App Store for a listing of breweries attending, special releases, food vendors and other important event details.
2026 Date TBD
Arctic Ale & Art Walk – February 22, 2025
By the end of February we are all ready to get out of the house and break the cabin fever! Arctic Ale & Art Walk is your cure for the winter blues and entice you into Downtown Freeport for a sampling of local beer, shopping and exhibits by local artists and artisans all while enjoying your favorite downtown stores. Live music fills the streets at warming stations throughout downtown as you stroll during this Freeport Festival District day (link to City’s Festival District page). The cost for the tasting is $10 for a wristband and cup. It can be purchased at the Greater Freeport Partnership during the event from noon to 4 pm at 110 W. Main St, Freeport.
For more information, visit the event Facebook page
2026 Date and Location TBD
Stephenson County Home Show – April 12, 2025
Do you have your eye on a home remodeling or landscaping project this season? Come meet with contractors and suppliers all in one space! The Stephenson County Home Show returns to the Stephenson County Fairgrounds, Saturday April 12 from 10 am to 4 pm. Visit with professionals in several service industries to tackle your next home project knowing you’re in good hands. See you for the Home Show on April 12.
Interested in becoming an exhibitor? Click here for information!
Pretzel Fest – April 25, 2026
Join us for Downtown Freeport’s second annual Pretzel Fest! Living in Pretzel City, whether you are a graduate or a local resident, the pretzel is honored and revered. In celebration on National Pretzel Day on April 26, we are hosting the best Pretzel Fest the salty snack has ever seen a day early! Activities include performances, food vendors, community organizations, and more! Pretzel Fest will also be an opportunity to enjoy the Downtown Freeport Festival District – purchase your alcoholic beverage from participating restaurants/bars and carry it with you through the downtown festivities!
WE BROKE THE RECORD FOR BIGGEST PRETZEL FORM in 2025!
For more information on this awesome event and new record, check out all the details on Pretzel City USA.
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