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

Music on Chicago – June 7, July 5, August 2

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 7 – In the Stix w/DJ Cup
July 5 – Harlan Jefferson & Mimi on the Mic
August 2 – 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 2023!

Cruise Night

We are bringing Cruise Night back to its original roots! Great cars and amazing car people!

Hot rods, rat rods, street rods, muscle cars, antiques, coupes, convertibles, sedans, trucks, motorcycles, and station wagons will all be part of this year’s Cruise Night in Downtown Freeport. Enthusiastic car collectors from across the Midwest will gather to showcase their unique vehicles and admire others’ prized possessions. 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 powerful, young people gained mobility and gathered downtown to hang out. Later in the night, the stoplights at each downtown intersection were put on flash mode, allowing continuous cruising. In Freeport, 45 years ago, a group of local car enthusiasts formed the Freeport Street Machines car club and would gather downtown to display their cars and socialize.

What they didn’t know is that their efforts would create the single biggest event in Freeport, attracting more than 10,000 people in one evening to celebrate cars. Cruise Night is more than just about cars; it’s about music, food, and most importantly, a gathering of great car people.

This year’s Cruise Night is on August 10. Expect to do some walking when you come down and make sure you bring your camera. Cars will be on display in several lots and on city streets throughout the downtown area. Souvenir shirts will be on sale at the information booth.

The event begins at 4 PM with the opening of the food court, so come hungry! Enjoy great music by Davis & Company as they provide a mood for the occasion from 4 to 8 PM. Don’t miss the new FAMILY FUN AREA sponsored by Alces Vehicle Storage. The cruising starts at 6 PM and goes until 8 PM, so cruise up and down Freeport and soak in the vibes.

For the Cruise Route Map, click here.

Pretzel City Brewfest – September 28, 2024

BUY TICKETS HERE!

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.

Arctic Ale & Art Walk – February 24, 2024

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). This is a FREE event, however please start your day by checking in to receive your tasting wristband and cup at the corner of Stephenson Street and Chicago Avenue from noon to 4 pm.

For more information, visit the event Facebook page

Pretzel Fest – April 27, 2024

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 of National Pretzel Day on April 27, we are hosting the best Pretzel Fest the salty snack has ever seen! Activities include a BBQ competition, performances, 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!
Dozens of boutiques, shops, and restaurants offer pretzel merchandise and food options to celebrate your favorite salty snack.

Stephenson County Home Show – April 20, 2024

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 20 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 20.

Pretzel City Winefest – May 11, 2024

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

Get your tickets here!

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 $25 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!

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