Are you interested in taking lessons or need a facility to ride in? Wyndham Oaks has several trainers and allows schooling rides to take place in any ring on the property. Trainers arrange their own lessons or have a scheduler, so please reach out to them directly.
Our ring fee is $25 and includes access to all of our riding facilities. We look forward to hosting you!
We take ring fee payments via check, cash, or digital payments. We accept Paypal at wyndhamoaks@gmail.com.
Whether you are trailering in to take a lesson, want to practice for an upcoming show, or want to hit the trails, Wyndham Oaks has plenty of space to ride. Our facilities include 3 distinct arenas:
An oversized indoor arena (105’ x 200’) with translucent, hangar door windows to maximize air flow. We have custom footing that is dragged and watered 2x daily to maintain an excellent riding surface.
An oversized, outdoor arena with a full size dressage ring available for schooling Spring, Summer, and Fall.
Fenced jump ring. Nestled in the trees, this arena provides a more secluded setting and is ideal for starting young horses. Jumps are available for courses or gymnastic training.
Viewing areas and chairs for guests in each of the arenas.
Access to over 100+ acres of property to hack amongst the paddocks or exclusive equestrian trails for cool downs or cross-training.
Molly Xanthopoulos’ career has been enriched by a great journey in horsemanship. Her interest in the sport of dressage began in Houston, Texas where she quickly earned her USDF Bronze and Silver medals as a junior rider. Molly competed at the North American Young Rider Championships four times, and in 1991, helped her Region 2 team win the gold medal.
Molly’s riding education includes many years spent training in Europe at Reiterhof Moos in Salzburg, Austria as well as the breeding and training facility, Gestut Moosmuhle, in Weilheim, Germany. She was given the opportunity to work under Gunnar Ostergaard at his Deerwood Farm in Vermont and in Copenhagen, Denmark.
After achieving a solid foundation in horse training, Molly developed her dressage training business in 1994 out of her own North Star Farm in Xenia, Ohio. Her business grew into a successful home for horses and riders of all stages of training and diverse disciplines. Molly has started many horses under saddle and completed their education through Grand Prix. While training at her own farm, Molly earned her USDF Gold medal on a horse she imported as a three year old and trained herself. In 2005-2006, Molly took a year to intensively train in Bad Worishofen, Germany with Olympic Champion, Ulla Salzgeber. Her riding and showing was supported back in the US by Scott Hassler. Over the course of her riding career Molly has sought instruction from world renowned riders such as Nicole Uphoff, Debbie McDonald, Michael Klimke, and Ingo Pape.
In 2012, Molly decided to move her business to the East Coast and trains full-time out of Wyndham Oaks. As the resident trainer, Molly accepts horses into training programs as well as teaches lessons to students of all levels and multiple disciplines. Molly competes on her own horses as well as those of her clients at recognized shows all over Region 1.
As resident trainer, Molly is available 6 days a week (Tuesday-Sunday) and teaches evening lessons. She enjoys teaching all levels and has many trailer-in lessons.
Contact Molly at 937-903-3827 or at mollykxanthopoulos@gmail.com.
Tiffany Cunningham started her passion for horses as a young girl. That passion led her to study at Johnson & Wales University in Providence, RI. There
she secured a spot on the national title-winning Intercollegiate Dressage Team. After graduating with a B.A. in Equine Business Management, Tiffany went on to work with several barns in the North Shore area of Massachusetts before striking out on her own.
While running her own program, Tiffany produced several horses from green broke to competing at USEA-recognized events through the Preliminary and Intermediate levels. She has also earned her USEA Gold Medal for Novice and Training Levels, and her USEA Silver Medal for Preliminary Level and also received qualifying scores towards a judge’s card.
For riders, Tiffany focuses on creating a solid position and foundation of skills to help riders become thinking and feeling partners for their horses, regardless of the discipline. She has instructed riders in eventing, hunter, jumpers, equitation, dressage, trail/pleasure riding, and even worked with some western horses on occasion. She has held a Massachusetts Riding Instructor License since 2005 and has also participated in the USEA Instructor Certification Program for levels 1 & 2. Riders also appreciate her knowledge and ability to combine Pilates teacher training, through Balanced Body Pilates, with riding to help them better understand the biomechanics of riding.
Tiffany enjoys bringing along young horses and strives to create a relaxed, confident horse through systematic training, taking time to establish solid
basics on which to build. She has also worked extensively with problem horses and has had much success with helping horses and their owners turn their training around in a positive direction. Knowing how important it is to continue learning in the horse
industry, Tiffany has trained and ridden in clinics with highly regarded four-star eventing trainers Ashley MacVaugh, Robert Costello, Denny Emerson, Stephen Bradley, Amanda Wilson, Lucinda Green and
Mike Plumb. She has also ridden with Grand Prix
dressage trainers Rebecca Vick, and Tanya Rennie of Maine to help strengthen her flatwork.
Tiffany teaches several days throughout the week, offering both private and group lessons. She also offers lessons for younger riders on her pony, "Pirate" affectionately known as "Pie-Pie". The pony is her daughter’s tiny mount and allows Tiffany to provide ‘lessons for littles’. I’m sure that there are a couple of people here that would love to see their little one or grandchild on an adorable, small pony (but as you all know, be careful as it can be a lifetime addiction)!
Contact Tiffany Cunningham at tiff316@yahoo.com or 781-244-9955.
Rebecca Langwost-Barlow is a USDF Gold, Silver, and Bronze Medalist and one of the first USDF certified trainers to Fourth Level. She was a world-ranked Grand Prix rider on her self-trained Dutch gelding Gomerant. As the first recipient of the Dressage Foundation Scholarship, she trained under the renowned Olympian Dr. Reiner Klimke and Rolf Isselhorst in Germany. She also trained with Michael Klimke, Willy Arts, Conrad Schumacher, Hans Juergen Armbrose, Rudolf Zeilinger, Georg Theodorescu and is presently training with internationally acclaimed trainers: Morten Thomsen and Christoph Hess.
Becky is a USDF Certified Instructor and has a 5* Rider Rating. Becky is also a USDF L Judge. Becky is a frequent contributor to Dressage Today, Practical Horseman and other local publications as well as serving as a training and showing expert for many national magazines.
She has started many equine youngsters and has trained and shown horses to FEI levels including Grand Prix.
In 2017, Becky and her Hanoverian mare, Libertina. were Reserve Champion in Intermediate II in both the BLM and GAIG finals. Libertina was then chosen the AHA USDF Reserve Champion for Intermediate II in the All Breeds Awards. Becky also showed Tina in their first Grand Prix ride at the BLM’s and scored 65.5%.
In past years, Rebecca was an FEI rider for two USDF National Symposiums: for Dr. Reiner Klimke on the elite Hanoverian stallion Guderian and for Conrad Schumacher on the Grand Prix horse Gomerant. She and her self-trained Dutch gelding Nando continue to hold the distinction of being the only horse-rider pair to win the Prix St. George and Intermediate I in the same year at the BLM Regional Finals in Lexington, VA. These are just a few of her many accomplishments; she has taken many different horses to a large number of high-score and year-end championships at all levels over the years.
Becky’s experiences as a leading dressage trainer, as a competitive jumper, and as a backer of babies on the race track have given her a depth and range of knowledge met by only a few.
Becky runs her own farm on the Eastern Shore- Preston Farm and joins us 2 days a a week on Mondays and Tuesdays. Her lesson schedule is usually very full. Please contact her scheduler to get on the waitlist and see if there are any openings.
Contact Linda Crivella, her lesson coordinator, at 301-299-4019.
Erin has a very impressive resume, crossing over multiple disciplines. She is an FEI trainer and competitor in 3 day eventing and dressage and has spent a significant part of her career training young horses in various disciplines. She has her USDF Gold, Silver, and Bronze medals and is a 3* rider in eventing. Erin is a graduate “B” level pony clubber and one of the only Americans to go through the Young Riders Program in both dressage and eventing (2002 CCI** team gold).
Erin has had the privilege of training under some great mentors. From 2010-2011, She rode and worked for Ingrid Klimke in Germany also receiving lessons from Herr Paul Stecken, the renowned coach of Dr. Reiner Klimke. Erin’s time in Germany is where she learned first-hand about the importance of cavalletti work in every discipline as well as valuable training techniques and standards she uses in her program. In 2015-2016, Erin rode and worked for Boyd Martin and trained with Silva Martin. Erin also trains under Olympians Stephen Bradley, clinics with Lars Petersen, and has regular lessons with Scott Hassler.
Her system of training horses of all disciplines, backgrounds, breeds and ages is based on good horsemanship and cross training. She believes in making horses happy and wanting to work together with their rider. She loves to teach Cavaletti and gymnastics lessons. Erin is our principal jumping and gymnastics trainer.
Erin teaches at Wyndham Oaks 2 days a week, usually W/F. She runs her own personal farm. She regularly accompanies her students to events and coaches as well.
Contact Erin at 703-585-7669 or ebfreedman@gmail.com.
Many of you know Jaralyn Gibson, a long-time local trainer. In 2021, she sold her Maryland farm and is now based in the lovely White Fences community in Loxahatchee, Florida. In the summer months, she relocates to Rice, Virginia to escape the Florida heat and storms for July-September.
At Finesse Dressage her priority is to achieve a harmonious partnership with our horses and a solid understanding of the classical training scale. Jaralyn Gibson is a USEF "r" licensed dressage judge, has earned her USDF Gold, Silver and Bronze medals, and is an international dressage competitor.
The Finesse Dressage team competes frequently throughout USDF Region 1, 8 and 3. Jaralyn has helped many clients earn their USDF medals, qualify and compete at Regional Championships, the CBLM Championships and USDF National Finals and the NAYC.
We host clinics with her throughout the year. Please reach out to Wyndham Oaks if you are interested in getting on her clinic list.