Wyndham Oaks LLC

Wyndham Oaks LLC Whether you’re a seasoned dressage rider, an ambitious eventer, or simply passionate about horseback riding, Wyndham Oaks is your sanctuary.

Whether you compete or simply enjoy dressage, Wyndham Oaks is dedicated to providing the facilities, care and training your horse deserves. Designed by well known Blackburn Architects, PC, the design follows this goal by starting with the needs of the horse and finishing with the building. The Arenas

Indoor Arena
The indoor arena is 105’ x 200’ in size and features unique, large translucent wind

ow panels (42’ x 14’). These panels open mechanically, affording a open-air quality to the space in good weather. Ceiling fans keep air moving throughout the year. The main lounge in the clubhouse overlooks the indoor. Footing is a mix of sand, GGT, and rubber. The outdoor arena, a blue stone arena, sits atop one of the high spots of the property and provides a beautiful place to ride. The club house patio overlooks the outdoor arena, or spectators can simply enjoy the shade of the trees adjacent to one side of the ring or relax with friends in the gazebo. The Clubhouse
Community is an important part of Wyndham Oaks, so we have lots of spaces to facilitate interaction. Attached to the indoor is a climate-controlled lounge with viewing area, shower and kitchen facilities and a large stone patio, just right for those summer evenings. The main barn also includes a lounge and patio area. The Main Barn
Soaring ceilings and 28’ skylights highlight the light and airy main barn. Each 12’ x 12’ stall has a dutch door to the outside with sliding yoke gates on both the interior and exterior doors. Stalls and aisles have in-laid rubber floor mats. Dormers over stalls provide excellent natural ventilation. Ceiling fans supplement ventilation during the hotter months. Each stall has its own built-in cabinet for storage of everyday items. Four oversized wash stalls have windows for summer ventilation and overhead heaters for the cooler months. The main barn includes a heated lounge, patio, bathroom, work room, office and extra storage space. The tack rooms are never more than four stalls away from your horse. Tack rooms are heated, well-ventilated and have refrigerators. While weekly laundry service is provided, the workroom is a large, comfortable place to clean tack or take care of that last minute laundry before your next show. The Small Barn
Attached to the indoor is a small, six stall barn which mirrors the quality and design of the main barn. This barn includes its own heated wash stall and tack room. Generally, our trainers keep their personal horses and horses in training here. The Property
Wyndham Oaks is located in the Agricultural Reserve of upper Montgomery County, Maryland. Surrounded by miles of hay fields and maintained trails (most of which are protected from development through preservation easements) our 80 acre property is beautiful at all times of the year. Pastures have four board oak fencing and all but a few are separated by lanes. Various sizes of pastures are available for the horses from small paddocks to large fields. The Hay Barn
The hay barn provides stabling for up to 9 horses. Many people (and horses) prefer the quiet and peacefulness of the hay barn, even though it is a little removed from the indoor. A separate, heated section houses the large tack room. The hay barn also houses space for several of the farm’s staff, meaning they are always close at hand for the needs of the horses.

We are looking forward to our rainy-day FADS show tomorrow! The show will continue as planned, with tests being performe...
05/22/2026

We are looking forward to our rainy-day FADS show tomorrow! The show will continue as planned, with tests being performed in our outdoor dressage ring while our indoor arena remains available for warm-up.

Please note that trailers have the right of way on our driveway, and cars should only drive or pull off on our paved areas to prevent mud.

We have a rare opportunity for a mare to join us in West Field Board in late June. If you are interested, check out our ...
05/16/2026

We have a rare opportunity for a mare to join us in West Field Board in late June. If you are interested, check out our website or reach out using [email protected]

We have spots open for our Jennie Brannigan clinic on Friday, May 22! To register, email Tiffany Cunningham at TMCEventi...
05/14/2026

We have spots open for our Jennie Brannigan clinic on Friday, May 22! To register, email Tiffany Cunningham at [email protected].

We are looking forward to our second FADS show of the year being held at Wyndham Oaks on May 23! Entries will open on Ma...
05/04/2026

We are looking forward to our second FADS show of the year being held at Wyndham Oaks on May 23! Entries will open on May 9 and more information can be found at https://www.fadsshows.com/

Wyndham Oaks is excited to add a new, FEI dressage rider and trainer, to our outstanding group of trainers. Noel William...
05/02/2026

Wyndham Oaks is excited to add a new, FEI dressage rider and trainer, to our outstanding group of trainers. Noel Williams Dressage is offering lessons, training, and sales at our farm in Boyds, as well as clinics and virtual lessons. Noel has extensive experience with horses of all ages and levels, as well as riders at various stages of their journey. Noel focuses on correct basics and a strong foundation to systematically progress through the training scale and up the levels. She is empathic and patient in her approach, emphasizing confidence and trust in her horses.

To learn more about Noel and to get on her schedule, visit noelwilliamsdressage.com

We had a wonderful lunch and learn lecture on Wednesday with Dr Davis from Monocacy Equine about horse vitals! Thank you...
05/01/2026

We had a wonderful lunch and learn lecture on Wednesday with Dr Davis from Monocacy Equine about horse vitals! Thank you to everyone who was able to participate and for Betty and Corey for being our wonderful demo horses for the day. We look forward to hosting more educational events with Monocacy in the future!

Meet Tiffany Cunningham! Tiffany is one of the resident trainers here at Wyndham Oaks with excellence in eventing and bi...
04/29/2026

Meet Tiffany Cunningham! Tiffany is one of the resident trainers here at Wyndham Oaks with excellence in eventing and biomechanics. Tiffany is a trainer for both horses and riders in training and you can find out more about her on our website wyndham-oaks.com. To get on her lesson schedule, contact Tiffany directly at 781-244-9955.

We were delighted to see our friendly barn family join together at our 20th anniversary party today. Thank you to those ...
04/25/2026

We were delighted to see our friendly barn family join together at our 20th anniversary party today. Thank you to those who attended, those who couldn't make it, and to everyone who has supported us at Wyndham Oaks over the past 20 years. Cheers to many more wonderful years!

We are looking forward to hosting 5* event trainer  here at Wyndham Oaks on Friday, May 22nd! Registration and pricing T...
04/24/2026

We are looking forward to hosting 5* event trainer here at Wyndham Oaks on Friday, May 22nd! Registration and pricing TBD. You can learn more about Jennie Brannigan at https://www.branniganequestrian.com/

After several delays, we are delighted to warmly invite you to Wyndham Oaks’s 20th Anniversary Party.Wyndham Oaks was es...
04/14/2026

After several delays, we are delighted to warmly invite you to Wyndham Oaks’s 20th Anniversary Party.
Wyndham Oaks was established in 2005, and we are thrilled to celebrate this milestone with you and your families. Please join us for an afternoon of hors d’oeuvres and champagne as we toast to twenty more wonderful years.
The celebration will take place from 2:00–6:00 PM on Saturday, April 25th in the indoor arena lounge.
Please reach out to [email protected] to RSVP.

Address

19301 Bucklodge Road
Boyds, MD
20841

Opening Hours

Monday 12pm - 9pm
Tuesday 7am - 9pm
Wednesday 7am - 9pm
Thursday 7am - 9pm
Friday 7am - 9pm
Saturday 7am - 9pm
Sunday 7am - 9pm

Alerts

Be the first to know and let us send you an email when Wyndham Oaks LLC posts news and promotions. Your email address will not be used for any other purpose, and you can unsubscribe at any time.

Share