History of the Cheshire Point-to-Point

For those who would like to get a taste of Chester County color and tradition, a great place to start is at the Cheshire Point-to-Point Races.

Organized in 1946 by Mr. Stewart’s Cheshire Foxhounds, the history of the races is tied to the history of the hunt. Today’s race chairman is Jock Hannum, but it was his mother who was the driving force behind the Cheshire Point-to-Point and the Cheshire Hunt for decades.

Mr. Stewarts Cheshire Foxhounds was founded in 1912 by Plunket Stewart, the stepfather of Nancy Penn Smith Hannum, who made her joint master with him in 1945. In 1945, he appointed her Joint Master with him. In 1946, after the war, they started the races because it was fun. Back then, the event consisted of just three races: a ladies race, a heavyweight race and the open race for the Cheshire Bowl. This was a race people pointed to because the big prize in timber racing is to win the Maryland Hunt Cup and the Cheshire Bowl was the kind of course with the kind of fences that would help to get a horse ready.

Generating funds that go to the efforts and endeavors of land preservation, the races continue to be a major event today for the members of the Cheshire Hunt, as well as the entire community. Now featuring a total of eight races, the Cheshire Point-To-Point offers exciting racing as well as the opportunity to enjoy the beautiful countryside that has been preserved much as it was when the first races were held.

Each year, the Cheshire Point-to-Point races are held the last Sunday in March at the Plantation Field course, just off Route 82 outside Unionville. Gates open at 11 a.m. Post time for the first pony race is 12:30. In addition to two pony races, there are five races over fences and a flat race on the card. The admission fee for the races is by carload. Tickets are available in advance online or at the gate.

2021 Cheshire Race Day

Presented by Fly Advanced


The Louis Neilson III Memorial Amateur Apprentice Timber
2 Divisions
**NSA Sanctioned**
Presented By: BNY Mellon, Selkirk Partners, & Temple Gwathmey Foundation
Sponsored By: Laurel Hill Farm & Don Cochran
The Joseph Walker III Memorial "Cheshire Bowl"
Sponsored By: Cadwalader & Associates
The Miles Valentine Memorial Novice Timber
Sponsored By: Sam Slater & Lornie Forbes


The Kathee Rengert Memorial Amateur Apprentice Flat
Sponsored By: Mr & Mrs Michael Moran


The Jill Fanning Memorial Open Flat
Sponsored By: Joy Slater

The Joy Valentine Memorial Side Saddle Chase
Sponsored By: Westerly Farm & The Lamparski Family
In honor of Luckytohavehim

Lead Line Pony Race
Sponsored By: The National Bank of Malvern 


The Work to Ride Small Pony Races
In Honor of: Work to Ride

The Medium Pony Race
In Honor of: Chester County Food Bank


The Red Raven Large Pony Race
Sponsored By: Wendy & Richard Hendriks