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
Bootiful Saturday – October 26, 2024
Bring those sweet trick-or-treaters downtown Freeport for a FREE movie at the Lindo Theatre followed by treats from downtown stores. Casper the Movie will be show at 10 am at the Lindo Theatre and then make your way to all of your favorite downtown stores for trick-or-treating fun until 1 pm.
Jimmy Nick & Don’t Tell Mama Concert – November 2, 2024
Get ready for a night of electrifying blues and rock-n-roll with Jimmy Nick & Don’t Tell Mama! Jimmy Nick is an old-fashioned, guitar-slinging blues prodigy who cut his teeth in the legendary Chicago blues clubs of Kingston Mines, Rosa’s Lounge, and B.L.U.E.S. on Halsted. Schooled by the blues greats, Jimmy has quickly made a name for himself as one of the most dynamic performers in the scene.
Join us for a night of pure entertainment – revel in the concert, show off your dance moves, sip on delicious cocktails, and cherish moments with friends. Tickets are just $20 each, or you can elevate your experience by sponsoring a table for 8 at $200, ensuring reserved seating for you and your friends. Doors swing open at 6 pm, setting the stage for an evening filled with rhythm and melody. The show kicks off at 7 pm.
Over the past year, Jimmy has taken the blues world by storm, recording his first live album at The Raue Center for the Performing Arts, playing over 200 shows, and advancing to the semifinals at the International Blues Challenge in Memphis. He’s headlined at Buddy Guy’s Legends and B.L.U.E.S on Halsted, and was even featured on the WGN Morning News. Jimmy Nick has shared the stage with legends like John Mayall, Ted Nugent, Samantha Fish, and Gov’t Mule, and opened for blues icons such as Eddie Shaw and Bobby Rush. His third studio album, Rare Breed, has sold over 1,500 copies and features Eddie Shaw on Jimmy’s original blues track “Greedy Man.” With his motown-tight band, Don’t Tell Mama, featuring saxophone, bass, and drums, Jimmy Nick delivers high-energy blues and rock-n-roll that captivates audiences and forges instant fans. His electrifying guitar work, fresh harmonica, clever lyrics, and animated stage presence make every performance unforgettable. Don’t miss your chance to experience the blues like never before—join us for an incredible night with Jimmy Nick & Don’t Tell Mama!
Trans-Siberian Orchestra Tribute: Christmas Wizards
Christmas Wizards: A Night of TSO is an electrifying tribute to the Trans-Siberian Orchestra, featuring iconic holiday music, dazzling lights, and breathtaking special effects. Join us for a magical evening in the beautiful auditorium of the Freeport Masonic Temple to amplify the spirit of the holiday season. Doors open at 6 pm with the show beginning at 7 pm.
This classic rock holiday experience tells the story of Christmas around the world for all ages produced by a musical ensemble that is second to none, an angelic choir, and a state-of-the-art light show. Selling out theatres, Christmas Wizards is a Trans-Siberian Orchestra show that will have you dancing from your seats feeling inspired by the joy of the season. Christmas Wizards: A Night of TSO is proudly hosted in collaborative efforts by the Greater Freeport Partnership, Mayor Jodi Miller, and City of Freeport. All proceeds from the fundraising concert will be utilized for holiday decorations in Freeport.
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!
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!
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
Pretzel City Brewfest – September 28, 2024
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.
Key Industries
