Labor Day weekend in Prentice means one thing: Progress Days. The annual celebration has grown into one of the most anticipated community events in northern Price County, drawing visitors from across the Northwoods for live music, a truck show, a car show, a golf tournament, a co-ed softball tournament, and a carnival atmosphere that has been a local tradition for years.
The 2026 edition runs September 4 through 7, kicking off Friday evening and running through Monday. It is anchored by the Northwoods Truck Show, which we covered separately, but Progress Days is much more than that. It is a full weekend built around community fundraising, live entertainment, and bringing people together at Lions Park and the Prentice Fire Department. All proceeds from the weekend support the Prentice Lions Club and the volunteer fire department, two organizations that keep the town running year-round.
History of the Tradition
Prentice Progress Days has been a Labor Day weekend fixture long enough that nobody quite remembers exactly when it started. What is clear is that the event has grown significantly over the years. What was once a small town picnic with a softball game has turned into a four-day festival with nationally touring musicians, a truck show that draws rigs from across the Midwest, and enough activities to keep a family busy from Friday through Monday.
The addition of the Northwoods Truck Show in 2020 was a turning point. That event brought in a new crowd—truckers and their families—and gave Progress Days a marquee attraction that extended the weekend beyond just the softball tournament. The golf tournament, named after Leo Heikkinen, honored a longtime community member and gave the weekend a third competitive event. Together, these pieces form a weekend that has become a destination event for Price County.
Family Fun, Parade, and Sunday Events
Progress Days is built with families in mind, offering a full schedule of community-focused activities at Lions Park. Saturday morning starts early with a Pancake Breakfast from 7:00 AM to 9:30 AM, providing the perfect fuel before the Progress Days Parade rolls through town at 10:30 AM. Following the parade, the park hosts free kids’ rides and face painting beginning at 11:00 AM.
Sunday keeps the momentum going with a second Pancake Breakfast from 9:00 AM to 11:00 AM. At noon, the focus shifts to classic and custom vehicles with the Car Show at Lions Park, followed by a Corn Hole Tournament at 1:30 PM for those looking for some friendly, laid-back competition.
The Headliner: Pink Houses
Saturday night’s main stage at the Prentice Fire Department belongs to Pink Houses, a nine-piece Wisconsin-based band that covers rock, pop, country, and R&B. Their shows are high-energy, audience-driven affairs that run late into the night. Opening act is Hailey James Band, a five-time Midwest Country Music Organization award winner from Cottage Grove, Minnesota, with over 260,000 TikTok followers and a résumé that includes sharing the stage with Carrie Underwood and Diamond Rio.
Friday’s music kicks off with Firsthand High from 5:00 PM to 9:00 PM on the street dance stage, followed by the Jerry Schmitt Band from 8:00 PM to midnight. Saturday afternoon has Jon Peck and the Bad Dogs from noon to 6:00 PM during the truck show, before the main evening show at the fire department.
Co-Ed Softball Tournament
The co-ed softball tournament runs Saturday and Sunday, September 5-6, at Lions Park. Entry is $125 per team, with a 5-guy, 5-girl format. The entry fee covers two umpired games (opening and championship), with players umpiring the rest. Payout is based on 12 teams entered, and all entry fees are paid back as prizes. The deadline to register is August 15. Contact Butch Staroba at 715-820-3784 or send payment to 762 Riverspring Drive, Prentice, WI 54556. Venmo payments go to @Jennifer-Staroba.
Leo Heikkinen Memorial Golf Tournament
Monday, September 7 brings the Leo Heikkinen Memorial Golf Tournament to Prentice Pines Golf Course, located at 403 Center Street. It is a 3-person scramble format with a $90 per team entry fee. Registration starts at noon with a 1:00 PM shotgun start. Cash prizes are awarded in two flights, with payouts to the top two teams in each. Hole contests are set up on most holes, and there is a square raffle with payouts of $300, $200, and $100 at $10 per square—you do not need to be present to win. Contact Nikki Heikkinen at 715-780-0712 for more information.
Northwoods Truck Show
The seventh annual Northwoods Truck Show runs Friday through Sunday at MBS (929 Railroad Avenue). Friday evening has open registration starting at 6:00 PM and the Second Annual Glow & Show from 8:00 PM to 10:00 PM, where trucks are lit up brilliantly after dark. Saturday’s lineup includes the trucks joining the 10:30 AM town parade, with the main truck show running from noon to 6:00 PM.
Proceeds benefit the Lions Club and the Prentice Volunteer Fire Department. Registration is via non-perishable food donations. Full details are available in our separate article Ripsaw Saloon in Prentice serves beef tallow fish fry, Wisconsin Old Fashioneds, and more.
The Community Behind It
What makes Progress Days work is the same thing that makes Prentice work—volunteers. The Lions Club supports the chicken dinner, helps with live music, and assists with cleanup. The fire department hosts the main stage acts. Local businesses donate to the prize pools. The campground opens up for out-of-town visitors. Every dollar raised goes back into the community.
Riverside Campground at 1599 Dr. MacKinnon Drive has electric-only sites for $20 per night on a first-come, first-served basis. For the convenience of campers and drivers, showers are available at the Prentice High School locker room and the Prentice Travel Center.
Prentice may only have about 600 residents, but Progress Days proves that small towns know how to throw a party. Whether you are there for the trucks, the music, the softball, the golf, the car show, or just the pancake breakfasts and free kids’ rides at Lions Park, there is something for everyone.
If you have never been, this is the year to change that. If you grew up coming to Progress Days, you already know why you keep coming back.
For full details and registration, visit progressdays.com.
See also: our complete Price County fishing guide, our guide to free camping in Wisconsin, our 48-hour Price County itinerary and what makes Price County communities special
See also: our complete Price County dining guide
See also: our guide to every town in Price County
See also: supper clubs within an hour of Price County
Frequently Asked Questions About Prentice Progress Days
When is Prentice Progress Days 2026?
Prentice Progress Days is held annually in July. The 2026 dates and full schedule are posted on the Prentice Progress Days Facebook page and village website as the event approaches. Source: Village of Prentice official website.
Where is Prentice Progress Days held?
Events take place throughout Prentice, Wisconsin, including the village park, ball field, and downtown area. Prentice is on Highway 13 in southern Price County, about 25 miles north of Phillips. Source: Village of Prentice.
What events are at Prentice Progress Days?
The festival typically includes live music, softball tournament, golf outing, food vendors, a parade, and family activities. The event is organized by community volunteers. Source: Prentice Progress Days historical programming.
Is there an admission fee for Prentice Progress Days?
Most events are free to attend. Some activities like the softball tournament or golf outing may have registration fees. Source: Village of Prentice.