Gypsy Cowgirls

Roamin’ the land,
riding fine horses
By Kay Tessum
Photography by Dawn Sanborn Photography

For many years we were moms supporting our kids in the 4-H horse project. As it is in life, the kids moved on, but the horses stayed. It was a pivotal moment for us—ride them or sell them. We chose to ride them. 


Some of us had horseback riding experience. Some came from a farm background. One of us (me) had no experience at all. We started slowly with short rides around the area. As we grew braver, we started venturing out to new lands. This led us eventually to ride in South Dakota, Wyoming and many other places. We have now been riding together for over 25 years. 

As we got older and retired, with aged horses, we made another life-altering decision. Even though we continue to ride our horses locally, we decided to leave them at home and take on a new challenge. We would venture out without our horses, ride new and beautiful lands, rent horses wherever we went and learn new things about our country, thus our name, Gypsy Cowgirls.


Over the years some cowgirls have come and gone, but our group remains “stable.” Our first ride was at Gettysburg National Monument. One of the cowgirls saw that the TV show “America by Horseback” was having a filmed ride there. We rode the battlefields of the north on a three-hour guided tour. We then rode the southern battlefields, another three-hour tour. 

Our second ride took us to Asheville, North Carolina, to ride at the famous Biltmore Estate. This was a beautiful rolling ride that took us right in front of the mansion. We also rode through Dupont Forest, the site of the filming of the movie “The Hunger Games.” We went to small, local craft museums and up to one of the trailheads of the Appalachian Trail. We spent one day at the beautiful Tryon International Equine Center. This is the location of the first FEI World Equestrian Games in the U.S., which was held last fall.


The criteria for choosing our destinations include good and safe horses, warm weather, lots of history and great food. We often say to others, “We came for the horses, but we stayed for the food.”

This spring we traveled with seven cowgirls to Tybee Island and Savannah, Georgia. We flew into Jacksonville, Florida and drove up the Atlantic Coast to Tybee Island, stopping along the way at Jekyll Island and St. Simons Island. Our vacation rental was on the beach on Tybee Island, an area of about three square miles. Our horseback ride was scheduled for the next day on Daufuskie Island, a small island a 30-minute water-taxi ride away. 

Daufuskie was settled by the Gullah, a group of freed slaves, after the Civil War. The terrain is varied, and the history is deep. Our riding stable was a short golf-cart ride away through moss-laden trees and gravel roads. Our original goal was to ride on the beach; however, due to it being turtle nesting season, we were only allowed to go so close. We rode over two hours with our equine guide who was an environmental biology graduate. She narrated many facts and stories about the area. Later in the week, we had a sea-horse adventure.

It is said, “You must go on adventures to find out where you truly belong.” I would add one more thing to that statement: “Surround yourself with people who make you hungry for life, touch your heart and nourish your soul.” I would say this beautifully sums up our group. We are in the process of planning next year’s trip, so any suggestions would be greatly appreciated.

Kay Tessum is a retired Rochester teacher. She is the mother of two and grandmother of three. She and her husband Steve live on a horse acreage near Rochester.