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History and Mission

The riding program has been an important part of the Dana Hall School’s campus life since the 1930s, when Mr. Frederick W. Boswell led the program. Over its long history, the program has produced many talented riders and competitors, including two Olympians.

The current equestrian program is nationally recognized with approximately 80 students, and it has been transformed under the leadership of Director Sarah Summers ’98 and retired Head Trainer Cookie DeSimone. The KSEC has trained riders who have achieved success at the local, regional and national level. Students also have opportunities to compete at both local and "A" rated shows on the East Coast and the Wellington Florida circuit in the winter.

KSEC is represented regularly with riders qualifying and showing at the USEF Pony Finals and regional and national equitation finals, including the prestigious fall indoor horse shows. Dana Hall also has a strong presence in the Interscholastic Equestrian Association (IEA) Zone I, with many team members qualified to participate in the Zone and National Finals each year. Dana Hall is proud to be the home of the 2008 and 2011 National Champion Middle School Team.

Leaving A Legacy


Karen Stives, Cookie DeSimone and Greg Best have each played a role in elevating Dana Hall's equestrian program to even greater heights. 

Karen Stives '68

Karen Wennbergh Stives '68 is an equestrian Olympic medalist, winning both the gold and silver medal at the 1984 Olympics. Stives was the first woman to win an individual Olympic Three-day event medal (silver). Along with the members of the 1984 United States equestrian team, Stives also took home the gold Three-day event medal. In the Three-day event, a rider and a horse complete a dressage test, cross country course and show jumping course.

Stives was the USCTA Rider of Year in 1981, 1987, and 1988. After retiring, Stives served as a FEI judge and chair of the USET Three-Day Event Selectors' Committee. In 2014, Stives bestowed Dana Hall with a $3.5 million dollar gift to Dana’s first-class equestrian program, which was given in her name: The Karen Stives '68 Equestrian Center. Stives passed away in August of 2015.

Cookie DeSimone

One of the the most respected horsewomen in New England, Christine "Cookie" DeSimone's love of horses began as a child when she would trek each day to see the horses at Dana Hall. After teaching riding at Dana Hall for forty-four years, DeSimone retired in 2016, and continues to stay connected to the program. During her career, she coached two IEA National Team Championships and produced countless champions in the hunter, jumper and equitation divisions. Her juniors qualified for the Medal, Maclay and USET finals, as well as the NAYRC-North American Young Riders Championships. Along with Greg Prince she is the head trainer and co-owner of Woodridge Farm, as well as a co-chairwoman of the New England Equitation Committee.

Greg Best

Greg Best is an Olympic show jumping veteran. Best is most well known for his partnership with the gray American Thoroughbred show jumper Gem Twist. Together, the duo earned individual and team silver medals at the 1988 Seoul Olympics and placed fourth at the 1990 World Equestrian Games in Stockholm. Although he resides in New Zealand, Best spent much of his time traveling and teaching clinics all over the world until he became the head trainer at Dana Hall School in 2016. Today, Best comes to Dana Hall in the summer for his Summer Training Academy camps.