Windsor: Rodeo, Parks and History

New Windsor combines local festival traditions, equestrian sports and public places with a history that remains visible in everyday life in the community. Those planning a trip with special events, small discoveries and time outdoors will find several different points of interest here. When choosing your holiday rental, it is worth first considering whether your stay will be shaped primarily by the annual fair, historic sites or sporting activities.

Rodeo and Horse Shows as Part of the Community’s Character

An important date on the events calendar is the annual “New Windsor Fair, Rodeo and Horse Show.” It takes place at New Windsor Rodeo Park from the third Thursday through Saturday in August. The event combines a fair, horse shows and rodeo, giving a trip to New Windsor a clear seasonal focus. The youth horse show program also includes an open “Jackpot” barrel racing class with additional prize money.

The history of this tradition goes back further. The “New Windsor Homecoming and Horse Show” was held in mid-August 1935 as a community event featuring horse shows, a fair, agricultural exhibitions and homemaking exhibits. When the event resumed in 1947, rodeo was added to the program of the “New Windsor Fair, Rodeo, and Horse Show.” Those interested in regional festivals and their development can incorporate these historical connections into their own trip planning.

Historic Details at New Windsor Depot Park

New Windsor Depot Park offers a different focus. The park includes a historic hitching post and a historic tower with a bell. Decades ago, the bell alerted volunteer firefighters. The park also features a pavilion or bandstand, as well as several memorials. This makes it a suitable destination for visitors who want to discover smaller historic details and memorial sites in addition to attending an event.

The New Windsor Depot Bar & Grill is also part of the local character. It is located in the former railroad depot and offers a place to meet, drink and eat. Together with Depot Park, it provides an insight into the connection between the community’s history and present-day life, without requiring the stay to revolve exclusively around a major festival.

Free Time, Parks and the Rodeo Run

New Windsor maintains three publicly accessible parks. There is also a tennis court and a basketball court next to the municipal building. You can take these places into account when planning a trip that includes free time and exercise in the community in addition to events. Which stops matter most depends on your preferred travel pace and the interests of your group.

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

Choose Accommodation Based on Your Desired Travel Experience

When searching for accommodation in Windsor, you can first organize your trip by theme: The New Windsor Fair and the horse shows call for planning around the August date, while New Windsor Depot Park, historical background and the public facilities offer interesting points of reference even independently of a festival date. Those who want to follow sporting events can include the Rodeo Run as a separate retrospective element in their planning. Those who want to discover community life and the history of the town can focus their stay more on New Windsor Depot Park, memorials, the former depot and local dining.

A holiday apartment or holiday home should therefore primarily suit your preferred itinerary. As you continue your search, check which accommodation best complements your travel dates and planned activities. This leaves room for New Windsor’s defining experiences: horse shows and rodeo, historic sites, public parks and events with strong ties to the local community.

For the broader travel overview: Mercer County.