Our “The Keepers” Ponies

Rollingwoods Sleightly Black LOM

(*Sleight Of Hand OD/AOE/LOM x Timbercreek Blackberry)


Sleightly Black earned her individual LOM in style winning Supreme Champion in 2011 at both the Red River Welsh Show and the Fieldstone Park Welsh show.  Sleightly Black began her career taking care of Ruth and as she aged she of course entered the hunter world.  She was shown lightly and then returned to Rollingwoods to take care and educate our future riders.  She is patient and kind and will jump whatever she is pointed at regardless of how she is ridden.   She is loved by Turner Davis and his mother like no other pony at Rollingwoods because she always brings him back safe.

Rollingwoods Berry Last One & Rollingwoods Back in Black (aka “The Boys”)

(Sleight Of Hand OD/AOE/LOM x Timbercreek Blackberry)

Berry is quite an instructor for our driving students. He has big beautiful movement, knows his job and helps our students safely see correct versus incorrect reining. Berry drives both singly and as a pair and has competed extensively in CDE’s and pleasure drives. He is strong, a big mover, very willing to work and most importantly, tons of fun.

The Boys were driven by Rob McCartney with Joanna Wilburn as Navigator in the KY Gala Combined Driving Event (photo above) Placed: Champion Preliminary Division, Best Marathon Preliminary.

 Rollingwoods All Mine


Rollingwoods Easy Choice

(Rollingwoods Easy as L LOM x Practically Perfect)

Lex is our superstar from our stallion, Rollingwoods Easy as L. Our trainer, Judy Fendley, who did such an outstanding job with his father, has taken this special pony on as a dressage prospect. Meanwhile Sally Ross who also loves this pony is showing him in the Welsh world. He is a phenomenal mover, incredibly athletic, and gotten good ribbons the few times he has been shown. Look for him in the future because this pony is going places.


The Broodmares

Rollingwoods Sticky Fingers LOM

(*Sleight of Hand OD/AOE/LOM x Rollingwoods Stuck on You LOM x *Pendock Masterpiece LOM)

Sticky has had a long and storied career at Rollingwoods. She was first successful with Michelle Casperson in the hunter world with too many championships to mention. As she aged she has come home to the farm to take care of our niece, Kelli West, as she learned to jump. She has been super successful in the welsh world earning her LOM in 2010 as well as National Champion in Hunter and English Pleasure. Perhaps her biggest asset is her temperament as she and Mason Davis at age 4 have proven very competitive in the pet pony obstacle.

Ozark Let’s Rock AOE/LOM

(Alra Jasmine x Severn Sirocco)

Sometimes you acquire a pony for one reason and wind up loving it for a host of other reasons.   Lettie was leased to us to complete the Sire LOM for her dad, Severn Sirocco.  After showing her we realized that this mare was special and purchased her immediately.  She has excelled in the driving arena but her biggest success has always been in pet pony obstacle.  Children will fight over who gets to lead her because she has excellent ground manners and will not step on the smallest child.

Rollingwoods Elles Belles

(*Sleight of Hand OD/AOE/LOM x Gayfields Mona L LOM x *Pendock Masterpiece LOM)

1996 Section B grey Mare – 12′ 3 ½” hands. – “Ellie” is a full sibling to Rollingwoods L on Wheels and Rollingwoods Picturesque. She is currently jumping courses with auto changes. Will win the model, hack and over fences.

Rollingwoods Unequaled

Rollingwoods Unrivaled

Rollingwoods Unbelievable

Rollingwoods Stick to it

Rollingwoods Stick Em Up


Rollingwoods Catfish Cookies


Rollingwoods Top This

Rollingwoods Classic Rock

Left: Nora Land driving, Ruth Wilburn, DVM riding.  Right: James Mason Davis & Rollingwoods Classic Rock waiting on their walk trot debut. Gotta love a pony that will take care of her rider.

Rollingwoods Top Knotch