Windsor: Fair, Rodeo, and Depot History

When looking for hotels in Windsor, event dates and local history can offer different clues for choosing your travel dates. The annual fair takes place during a recurring period in August; there are also historical festival dates, a dated race, and public facilities. When planning, it is important to distinguish the fair date given annually from details about individual programs and events.

Fair, Rodeo, and Festival History

The annual “New Windsor Fair, Rodeo and Horse Show” takes place at New Windsor Rodeo Park from the third Thursday through the following Saturday in August. If the fair is the reason for your trip, you can use this three-day period as a starting point for choosing your travel dates. Check the dates for the specific edition before you travel.

The festival’s history spans several milestones. In mid-August 1935, the “New Windsor Homecoming and Horse Show” was held as a community event featuring horse shows, a fair, agricultural exhibits, and homemaking exhibits. When the event resumed in 1947, the rodeo was added to the program, and the name “New Windsor Fair, Rodeo, and Horse Show” was adopted.

The 2026 youth horse show program includes an open “Jackpot” barrel-racing class with additional prize money. For those interested in equestrian sports, this is a specific event in the youth program.

Race and Parade

The 36th annual New Windsor Two & Four Mile Rodeo Run was held on August 22, 2025, at New Windsor Ball Park on the western edge of New Windsor, Illinois, along Illinois Route 17. The race started and finished at the east entrance to the rodeo grounds and followed paved roads.

For the New Windsor Street Parade, the horses and riders line up in the South Front parking lot on Route 17. Since this information is tied to the event schedule, check the lineup location again before you travel.

Depot Park and Public Facilities

New Windsor Depot Park is in the center of New Windsor. A historic hitching post for horses stands there beside a historic tower. A bell on the tower alerted volunteer firefighters decades ago. The park also has a pavilion or bandstand, as well as several memorials. Those interested in local history will find different points of interest here than at the fair and rodeo: the park brings together historic features and memorials.

New Windsor maintains three parks open to the public. A tennis court and a basketball court are also located beside the municipal administration building. Alongside events and history, public parks and sports courts provide additional local points of reference.

Dining in the Former Depot

New Windsor Depot Bar & Grill is located in the former railroad depot and offers a place to meet, drink, and eat. This dining option with a connection to the depot complements the town’s historical attractions without being the same place as New Windsor Depot Park.

For the broader travel overview: Mercer County.