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.

Don’t forget to check our Calendar of Events for things that may be happening on any given date and our weekly digital ALL IN Stephenson County events guide for what is happening in the upcoming week!


Upcoming Annual Events

Pretzel Fest – April 24, 2021

Pretzel City Winefest – May 22, 2021

Wine enthusiasts from around the region flock to Downtown Freeport  to enjoy great shopping, food and, of course, wine at the third annual Pretzel City Winefest!

Wineries 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 show them the wonderful shops and restaurants Freeport has to offer.

A $20 general admission ticket includes 10 tasting tickets, souvenier tasting glass, tasting hours noon – 4 pm, and wine bag.
A $40 VIP admission ticket includes 15 tasting tickets, souvenier tasting glass, wine glass lanyard, event t-shirt, cake pop, wine bag and tasting hours from 11 am – 4 pm (one-hour early-bird  entry before general admission!).

Music on Chicago – First Friday in June, July & August

June 4, July 2, and August 6, 2021

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! Our June event will take place at Downtown Freeport’s new Art Plaza at the corner of Chicago Avenue and Douglas Street. We are excited to be the FIRST event on the beautiful grounds.
For only $5 admission, you can join the fun, listen to music and dance the night away. Local food vendors are available for dinner options and volunteers serve alcoholic and non-alcoholic beverages during the event. Come join the fun in 2021!

Cruise Night – August 14, 2021

Reserve your parking spot here!

Hot rods, rat rods, street rods, muscle car, antiques, coupes, convertibles, sedans, trucks, motorcycles and station wagons will all be part of this year’s Cruise Night in downtown Freeport . Diverse car collectors from as many as five states will gather to display their special vehicle and gaze at everyone else’s. Cruise Night is a celebration of a less hectic time before cellphones, video games and social media.
In the 1950s and ’60s as cars became more accessible, and more powerful young people became mobile and they gathered downtown to hang out. Later in the night, the stoplights at each intersection downtown were put on a flash and so traffic didn’t have to stop and the cruising of the circuit began. In Freeport, 43 years ago a group of local car enthusiasts came together and created a car club called Freeport Street Machines and they would gather downtown to display their cars and hang out.
What they didn’t know is that their efforts would create the single biggest event in Freeport attracting more than 10,000 people on one evening all to celebrate cars. Cruise Night is more than the cars though. There is live music, food and most of all it is, a gathering of family and friends.

Expect to do some walking when you come down to Cruise Night and make sure you bring your camera and lawn chair for the Cruise. Cars will be on display in several lots and on city streets throughout the downtown area. Souvenir shirts and citywide 50/50 tickets will be on sale at the information booth. The event begins at 4 p.m., an hour earlier this year, with the opening of the food court so make sure you bring your appetite too. FHN is sponsoring the entertainment stage, which will feature local band Mr. Ed from 6 – 9 p.m.
The family fun area is open from 4 – 7 pm which will feature blow-up entertainment for children. The Gary’s Collision & Customs Muffler rapping contest starts at 5  pm and Dan’s 66 burn-out contest at 6 pm. These contests are a must see and hear! The cruising starts at 7 pm, heading east on Douglas, south on Adams, and west on Main and north on Van Buren back to Douglas.
Greater Freeport Partnership, along with a committee of volunteers, organize the event recruiting over 70 volunteers, obtaining sponsors, applying for permits and scheduling the evening events in the yearlong planning process. To volunteer please call 815-233-6301. And continue to check our Facebook Event page for more details as the event draws closer.

Pretzel City Brewfest – September 25, 2021

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 $30 general admission ticket online which includes entry, 20 tasting tickets, and a souvenir glass. There will be a  limited number of $60 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, VIP lounge, and an option to buy a discounted limited edition Pretzel City Brewfest hoodie (not available to the general public).

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.

Bootiful Saturday – October 30, 2021

Bring the kids Downtown Freeport and enjoy a fun, child-appropriate Halloween movie at the Lindo Theatre and then take to the streets of the downtown district to trick-or-treat from local shops.

Mistletoe Walk – November 21, 2021

The holidays come a little early in Downtown Freeport! The weekend before Thanksgiving we are already getting shoppers in the mood for the shopping season with decorated storefronts, visits from Santa, lighting of the Holiday Hero Tree as well as specials from our MANY local boutiques and stores. For a full list of shops, please visit our Shopping page.

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Pretzel City Winefest offers shopping fun May 22 May 18, 2021 Freeport, IL – The Greater Freeport Partnership will host the fourth annual Pretzel City Winefest this Saturday, May 22 from noon to 4 pm. Tickets are still available for sale online for $25 at greaterfreeport.com/events.  After purchasing your tickets online, check-in at any of the five downtown restaurants to receive your Winefest glass, lanyard, bag, wine tokens and information packet with information on […]
Ribbon Cuttings announced for Freeport businesses May 18, 2021 Freeport, IL – The Greater Freeport Partnership is excited to announce the opening of several new businesses in Freeport.  Ribbon-cutting ceremonies are being held to celebrate these businesses and all are invited to join. Ribbon cutting ceremonies will be held at the following business locations: The Space Salon Studio at 2 E. Stephenson St. – May 27 at 10:30 am. […]