The weekend brings the Tailgate Tee-Off and Picklefest 2025, along with fundraisers, live music and more to the Freeport area.
The Tailgate Tee-Off
What: The final couples twilight event of the season brings together everything good about late summer: twilight golf, tailgate food and getting ready for football season. Fee includes registration and cocktails at 5 p.m.; nine-holes of golf teeing off at 6 p.m.; tailgate dinner after golf, on-course games and prizes. Football-themed attire is encouraged: think football jerseys, team colors or any game day gear you’d wear to a tailgate party. The menu will feature classic tailgate favorites.
When: 5 p.m. Friday, Aug. 29
Where: The Freeport Club, 1614 S. Park Blvd., Freeport
Cost: $60 per couple; $40 for members
Blue Steel
What: RAMI-award winning BLUE STEEL was forged in the fire of two music styles: Country and Rock.
When: 7-11 p.m. Friday, Aug. 29
Where: Hooks & Bobbers, 612 Bridge St., Winslow
The Groove Hotel
What: The Groove Hotel will perform.
When: 7-10 p.m. Friday, Aug. 29
Where: The Great Debate, 1 E. Spring St., Freeport
Pecatonica Labor Day 5K
What: The Pecatonica Labor Day 5K and Family Fun Run was inspired by Pecatonica’s Crooked River 5K. In remembrance of the Crooked River 5K, the race will start at the Pecatonica Public Library, go down to the Winnebago County Fairgrounds, follow along the Pecatonica River Bike Path, then follow back to Pecatonica Public Library. The awards ceremony will be held at approximately 9:30 a.m.
When: 8 a.m. Saturday, Aug. 30
Where: Pecatonica Public Library, 400 W. 11th St., Pecatonica
Cost: $37
Rosie’s Fall Market
What: Rosie’s will be debuting new fall drinks and will have your favorite fall pastries, new clothing merchandise, fall candles and more from some favorite small businesses, From 8 a.m. to noon, Wave Avenue Boutique will be out front with fashion finds; Greenlight Floral will have make and take bouquets; Thread of Life will be set up inside with handmade bags.
When: 8 a.m. – 3 p.m. Saturday, Aug. 30
Where: Rosie’s Coffee Company, 507 Main St., Pecatonica
Tour: Pettit Chapel and Laurent House
What: Enjoy a unique combined tour of two Frank Lloyd Wright-designed buildings from two distinct periods of the architect’s career: the 1907 Prairie-style Pettit Memorial Chapel in Belvidere and the Usonian-style Laurent House in Rockford, designed in 1949. The Pettit Chapel, named in honor of Dr. William Henry Pettit, was donated to the Belvidere Cemetery Association by his widow, Emma Glasner Pettit. Mrs. Pettit commissioned Frank Lloyd Wright to design the chapel in late 1906; construction was completed in 1907. The chapel remained in active use until the 1920s. After decades of disuse and neglect, it was restored and reopened to the public in 1981. The tour will start at the Pettit Chapel. Guests will then provide their own transportation to the Laurent House Visitor Center. The drive from the Pettit Chapel to the Laurent House takes about 20 minutes. The tour will be led by architect Andrew Wanek, ALA.
When: 1-3 p.m. Saturday, Aug. 30
Where: Pettit Chapel, 1121 N. Main St., Belvidere
Cost: $45
David Rovics and Kamala Emanuel
What: Legendary protest and pro-labor folk singer David Rovics and Kamala Emanuel (AKA The Ministry of Culture) will play a live set. The suggested door donation helps Brother Rovics and Sister Emanuel continue to spread their message but no one will be turned away. Celebrate Labor Day Weekend with some pro-worker tunes!
When: 7 p.m. Saturday, Aug. 30
Where: Maze Books, 406 E. State St., Rockford
Cost: Suggested door donation of $10-$20
DFS Rockabilly Show
What: Dirty Fishnet Stockings will perform. There will be a cash bar and a food truck, too. Rock out between the exhibits.
When: 7-10 p.m. Saturday, Aug. 30
Where: Vintage Wings and Wheels Museum, 5151 Orth Road, Poplar Grove
Cost: $10 suggested donation to the museum
Ladies Night 2025
What: Get ready to ride, laugh and make memories! This is your chance to try the sport of BMX — no pressure, just fun. This is a free ride event — not a clinic. Men are welcome to join in the prize winning fun, but no men or boys are allowed on the track during the event. This is just for the women. First-time riders/non-members will need to acquire a free one-day membership for this event, which is available at the registration window. Bring a long sleeve shirt and pants. There will be free full-face helmet rentals and and bikes provided by the track. There will be a drawing throughout the day featuring prizes donated by local businesses, friends and the BMX industry. 100% of proceeds will benefit Womanspace of Rockford. Bring cash for tickets, available at the raffle table only. There will be free snacks and bottled water available. Please bring your own food if you have dietary restrictions. No alcohol is allowed.
When: 4-8 p.m. Saturday, Aug. 30
Where: Rockford BMX, 4950 Safford Road, Rockford
Cost: Free
Tube Races
What: Win $500 in cash prizes and more.
When: Noon Saturday, Aug. 30
Where: Hooks & Bobbers, 612 Bridge St., Winslow
Just 4 Fun Band
What: Just 4 Fun Band will rock the stage. Enjoy food, drinks and live music.
When: 8 p.m. – midnight Saturday, Aug. 30
Where: Best Dam Bar, 13965 Best Road, Davis
Picklefest 2025
What: Enjoy pickle-inspired food and drinks all day while they last, including fried pickles, pickle burger, pickle beer, new pickle slushies and more. Check out pickled items from local vendors and live music with Just for Kicks playing from 2-5 p.m.
When: 11 a.m. – 6 p.m. Sunday, Aug. 31
Where: Lena Brewing Co., 9426 W. Wagner Road, Lena
Coming next week:
Labor Day Celebration
What: See antique cars and trucks on display, get a steam train ride and a tour of the Silver Creek Museum. There will be an operating 130 Ton Cooper Corliss Stationary Steam Engine
Tractor and a lunch stand in the museum. Train rides run every hour on the hour from 11 a.m. – 4 p.m. There is no charge to view the Cooper Corliss but donations would be appreciated.
When: 11 a.m. Monday, Sept. 1
Where: Stephenson County Antique Engine Club, 2954 S. Walnut Road, Freeport
Cost: Museum admission is $4; free for children age 11 and younger. Train rides are $8 or $2 for children age 11 or younger.
Chessport
What: No experience is necessary to join ChessPort and no registration is required. Chess sets are provided. All current, former, rusty and new players are welcome.
When: 6-7 p.m. Wednesday, Sept. 3
Where: Freeport Public Library, 100 E. Douglas St., Freeport
Cost: Free
Bed Turning Event
What: The Bed Turning Event is part of the Art in Every Stitch: A Quilt Show programming. Featured artists will lift and “turn” quilts from a stacked bed, sharing the personal stories, techniques and inspirations behind each piece. Guests are encouraged to bring their own quilts to add to the “bed pile” and share its history in this community-centered tradition.
When: 4:30-6 p.m. Thursday, Sept. 4
Where: Freeport Art Museum, 121 N. Harlem Ave., Freeport
Kathi Edwards is a freelance contributor to the Freeport Journal-Standard
This article originally appeared on Journal Standard: The Tailgate Tee-Off is among 12 events happening this weekend in the Freeport area
Reporting by Kathi Edwards / Journal Standard
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