The weekend brings the Route 75 Garage Sales, Music on Chicago and The BOB 2026, along with fundraisers, live music and more to the Freeport area.
Dakota Rock-Grove United Methodist Rummage Sale
What: Find deals on clothing, home goods, toys and more. There will be free coffee all day and a lunch stand will be available. All proceeds go to support our church programs and local outreach.
When: 8 a.m.-4 p.m. June 4 and June 5; 8 a.m. – noon June 6
Where: 120 S. Church St., Dakota
Route 75 Garage Sales
What: The annual route 75 garage sales goes for 40 miles along highway 75 in northern Illinois from Freeport to south Beloit. Some sales will open on Thursday, June 4th as well.
When: 8 a.m. – 4 p.m. June 5 and June 6
Where: See illinoisroute75sales.wordpress.com for more information
Music on Chicago
What: Music on Chicago has been a tradition in downtown Freeport for more than 20 years. Bring friends, your family and blankets to take a spot on the lawn. Rollin Whiskey performs on June 5.
When: 5-9 p.m. June 5
Where: Freeport Arts Plaza, 15 Douglas St., Freeport
Healthy Kids Day
What: Enjoy healthy family fun with the Family YMCA of Northwest Illinois and Mercyhealth. Get wellness tips and participate in activities, booth activities with giveaways, an obstacle course, bounce slide and more. There’s even a chance to win some summer fun giveaways.
When: 5:30-7:30 p.m. June 5
Where: YMCA of Northwest Illinois, 2998 W. Pearl City Road, Freeport
Cost: Free
Free Aqua-Na Cycle
What: Ride the Grand Illinois Trail in sections across the state. From Tutty’s Crossing to Lake Le-Aqua-Na State Park, this 40-mile flat ride offers options to return on the same trail or detour and catch local brews on the way back.
When: 9 a.m. June 6
Where: Tutty’s Crossing, 104 Commercial Ave., Freeport
Cars & Coffee
What: Cars & Coffee – Rockford is held from 9 a.m. to noon the first Saturday of each month from April through October in, from 9 a.m. to noon. A different car group is featured each month. Anyone is welcome to register and participate. Enjoy coffee and food from Katie’s Cup, conversations about cars and a sense of community.
When: 9 a.m. June 6
Where: The RPS205 Administrative Building parking lots and along Seventh Street, Rockford
Cost: Free to participate or spectate
Rockford Area Pride Parade
What: The third Rockford Area Pride will include floats, community organizations, local businesses and thousands of spectators and participants filling the streets with joy, color and unapologetic pride. All are welcome to celebrate diversity, self and expression. This year’s grand marshals are Shelton Kay, Norm Knott and Lien Vu.
When: Noon June 6
Where: Downtown Rockford
Cost: Free
Serb Fest
What: Enjoy a weekend full of Serbian tradition, music, food, folklore, sports and entertainment for the whole family. There will be football and 3×3 basketball tournaments, children’s activities and traditional Serbian food. The folklore program starts at 3 p.m.
When: Noon – 9 p.m. June 6; 1-9 p.m. June 7
Where: Holy Ascension Serbian Orthodox Church, 4301 W. Riverside Blvd., Rockford
Cost: Free admission and parking; donations are welcome; food and activities may have costs
The Jimmys
What: The Jimmys will perform for the first time here. Enjoy funky blues, cold brews and tasty BBQ along the Pecatonica River. The Jimmys are an award-winning, high energy, six-piece funky blues band with touring experience throughout the U.S., the Caribbean and Europe. The band is led by seasoned keyboard and Hammond B-3 player Jimmy Voegeli. He is joined by Perry Weber on guitar and vocals, Chris Sandoval on drums, John Wartenweiler on bass and a horn section featuring Pete Ross on sax and Joe Goltz on trombone.
When: 6-9 p.m. June 6
Where: Hooks & Bobbers, 612 Bridge St., Winslow
Shakey Graves
What: Across his career, Shakey Graves, the performance moniker of Austin, Texas-born Alejandro Rose-Garcia, has created musical adventures tailored to each fan: burning CDs and putting them in personalized decorated bags, building intricate scavenger hunts that send fans in search of unique tapes and Bandcamp-exclusive releases.
When: 7:30 p.m. June 6
Where: Coronado Theatre, 314 N. Main St., Rockford
Cost: $30-$77
The BOB 2026
What: The Robert Feltmeyer Memorial Golf Classic is held to support community efforts. There will be 18 holes of golf, food and beverages on the course, prizes, merchandise for purchase and a silent auction. Music will be provided by The Discman. The dinner/steak fry starts at 4 p.m. The dinner costs $35.
When 9 a.m. June 7 (registration starts at 8 a.m.)
Where: Wolf Hollow Golf Course, 6546 N. Shippee Road, Lena
Sunshine Band
What: The band will perform your favorite songs.
When: 2 p.m. June 7
Where: Hooks and Bobbers, 612 Bridge St., Winslow
Sunset Strip
What: The Rockford-based 80s hairband tribute band will perform.
When: 2-5 p.m. June 7
Where: Lena Brewing Company, 9426 Wagner Road, Lena
Live at Levings: Southern Soul Party
What: Live at Levings 2026 is a summer-long concert and community event series celebrating music, culture and local talent on Rockford’s south side. Featuring a mix of southern soul, blues, jazz, dance and community showcases, the series brings together regional and national performers alongside local artists. From high-energy concerts and DJ battles to talent competitions and family-friendly celebrations, Live at Levings offers something for all ages. The featured performers on June 7 are DJ Neal Howard, DJ Alfresh, MC Dreadhead Cowboy, Kandrice Jackson, Theo Huff and Mike Clark Jr.
When: 5-8 p.m. June 7
Where: Levings Park, 1420 S. Pierpont Ave., Rockford
Coming next week
Summer Reading Program Kick-Off Party
What: Sign up for Summer Reading at our Summer Reading Kick-Off Party! Children who sign up at the party will receive a free book. We will also have crafts, tattoos, and games! In case of rain, our party will move inside the library.
When: 1-3 p.m. June 8
Where: Freeport Public Library, 100 E. Douglas St., Freeport
Learn to Make Adaptive Books
What: Adaptive books are modified reading materials with added visual supports. Presenter, Rita Angelini, has been making adaptive books for years. These books can be used with children with a variety of developmental differences, including autism, challenged fine motor skills, language delays and visual challenges. They can also assist reluctant readers. Family members, aides, community volunteers/groups, service organizations, social workers, teachers, librarians or media center helpers, and disability advocates are all welcome to this event. Learn how to turn a picture book into an adaptive book so that everyone can enjoy reading.
When: 6-7 p.m. June 9
Where: Freeport Public Library, 100 E. Douglas St., Freeport
Cost: Free
Dinosaur Family Bingo
What: Enjoy an afternoon of playing dinosaur themed Bingo. All children will go home a winner. This program is only for children, teens and their caregivers.
When: 2-3 p.m. June 11
Where: Freeport Public Library, 100 E. Douglas St., Freeport
Annual Homeschool Used Books Sale
What: Shop from the Stateline’s largest annual homeschool resources sale. You’ll find used prices on like new/clean conditioned textbooks, consumables, teacher and supplemental resources, readers for all levels, puzzles/games, lab kits, hands-on manipulatives and more. Find Pre-K to 12th grade learning fun from top resource companies in the market. Sales are by cash or check only. Infants in front/back carriers/strollers are welcome but no other children younger than 12 are allowed on the sale floor or in the building. This is not a Park Hills Church sponsored event; please do not contact the church. This sale is a fundraiser for the N.I.C.H.E. Parent group.
When: 4-7:30 p.m. June 11
Where: Park Hills Church, 2525 W. Stephenson St., Freeport
Kathi Edwards is a freelance contributor to the Freeport Journal-Standard.
This article originally appeared on Journal Standard: 40-miles of Route 75 garage sales among 14 weekend events around Freeport
Reporting by Kathi Edwards, Special to the Freeport Journal-Standard / Journal Standard
USA TODAY Network via Reuters Connect
By Kathi Edwards, Special to the Freeport Journal-Standard | USA TODAY Network
