Chester County’s rolling hills have long been the scene of world- class equestrian activities. Spring begins the season and every weekend in May majestic horses race along the countryside. Plan a tailgating weekend with friends and catch the excitement.

The season takes off with the 77th Running of the Cheshire Races. The annual tradition takes place along the rolling hills of Plantation Field in bucolic Unionville, Chester County on Sunday, March 31, 2024. The excitement of timber racing affords a fun day for all, horse enthusiasts or those just looking for a fun day out! 

On Sunday May 5, 2024, it’s the 46th annual Point to Point at Winterthur – a glorious day of steeplechase racing set amidst the splendor of Henry Francis du Pont’s Winterthur estate. Pack a picnic lunch or tailgate spread and get ready to enjoy one of the Brandywine Valley’s most stylish and entertaining sporting events!

The Willowdale Steeplechase has been a tradition of spectacular horse racing for 30 years. Families and friends gather to celebrate a day of country life and a showcase of equestrian talent with some of the nation’s finest steeplechase horses and jockeys on Satiurday, May 11, 2024. Willowdale is minutes from Longwood Gardens and the blooms are breath taking, plan to take in both and enjoy a truly memorable weekend.


The Radnor Hunt Races on Saturday, May 18, 2024 continue the spring tradition of steeple chasing in the Brandywine Valley. A highlight of Radnor is the parade of carriages. After the first race, carriage owners turn out in their finery, driving these distinctive vehicles to the delight of the crowd. Enjoy a tailgate picnic with friends and family while helping to win the race for open space. All proceeds from the Radnor Hunt Races benefit the land and water preservation programs of the Brandywine Conservancy in Chadds Ford, Pennsylvania.

The Devon Horse Show and Country Fair is one of the nation’s leading equestrian events. Beginning the Thursday of Memorial Day weekend, May 22 and running through June 2, 2024, Devon is the oldest and largest outdoor multi-breed horse show in the country. While drawing competitors from around the world, Devon epitomizes the local traditions and lifestyles of the famed Main Line.


As spring gives way to summer Polo takes the lead. Nestled in the heart of the area is the 300-acre Brandywine Polo Club (BPC), one of the oldest polo organizations on the east coast. This summer come out for Saturday Starlight Polo on select dates from June 1 through September, 2024. Experience exciting polo with music, food trucks and a pop-up bar. Gates open at 5:30p.m. and the action starts at 6:30p.m.

Ludwig’s Corner Horse Show and Country Fair is fun for the entire family. Held Saturday, Sunday and Monday of Labor Day Weekend (August 31 through September 2, 2024) the show has been a Labor Day tradition for generations of families for 80 years. In addition to the rider competition in three rings, there will be Horse Drawn Carriage demonstrations, food, crafts, entertainment and a variety of vendors. Later in September Plantation Field International Horse Trials take place, where top event horses and riders throughout the country compete in beautiful Unionville, PA. In addition to the competition, guests enjoy a robust vendor village and a terrific tailgating atmosphere along the country course.

Check out the Full Equestrian Season in Chester County’s Brandywine Valley.