We hope your journey to the 27th Orleton Farm Pleasure Driving Show will be a pleasant one and that you and your friends will enjoy the weekend filled with diverse driving classes and social events. You will begin to experience the history and tradition of carriage driving in the Berkshires.
As you drive up Prospect Hill from the Red Lion inn, which was a coaching inn and tavern established c. 1873, you will pass several of the former summer “cottages” of the late 19th century – including Bonnie Brae (now the Shrine of the Divine Mercy), Naumkeag (a Choate family residence), Oronoque – and you will shortly arrive at your destination: Orleton Farm.
Upon passing through the entrance of the Farm, you will marvel at the beautiful grounds and pageantry of the horse show and surrounding activities.
We would like to take this opportunity to thank you for sharing your enthusiasm for preserving the tradition of pleasure carriage driving by attending the show. This is the third year of a four day show at Orleton Farm. Colonial Carriage has expanded the format at considerable financial risk. The members know how much you will enjoy the show and encourage you to help the club meet their expenses with your generous support.
The first day offers the Combined Test and Driving Trial for VSEs, ponies and horses with Dressage and Cone classes.
On Friday morning, the Pleasure Show kicks off with Turnout classes followed by the Driving Trial Marathon in the afternoon. The three-day pleasure driving show 2026 schedule will continue to offer the Utility Vehicle Division, a Park Division, and a Picnic Class along with an American Heritage class and the Ride and Drive class. We also offer a Tandem Division and Unicorn/Four-in-Hand Division and continue with a Coaching Division added in 2019. The Maiden Horse/ Pony Division and the Trade and Commercial Vehicle Classes will also be offered.
We will also continue the three invitational classes: Best Lady Whip, Best Gentleman Whip, Concours d’Elegance to close out the show on Sunday.
2026 Announcements
Show Manager: Dr. Ann Willey Phone: (518) 392-6583 Email:ann@drwilley.net
Secretary: Ellen Ettinger
Dressage/Pleasure Show Judges: Francois Bergeron, Terry Pickett
Technical Delegate: James Thomas
- Kind reminder to Photographers:
You must request permission from the Technical Delegate before entering the ring. Appropriate attire is required in the ring following ADS Pleasure Driving rules: gentlemen must wear a coat or jacket and tie, ladies must wear conservative dress or slacks. Thank you for your contributions in serving our exhibitors, staff, and guests.
All About the Show:
Welcome to Colonial Carriage & Driving Society’s 27th Annual Pleasure Driving Show. Colonial Carriage & Driving Society and Orleton Farm are proud to play a part in promoting the history and tradition of pleasure driving here in the Berkshire Hills. The Berkshires had great history in the gilded age with the large estates and wonderful carriage houses as the place to come and be seen driving your horse and carriage. Harvey and Mary make their home at Orleton Farm, which has been in Mary’s family since 1900 and has always been a horse facility. The grounds have become home to Colonial Carriage for its many events held here throughout the year: sleigh rallies, clinics, fun day, club meetings, and the pleasure show.
The show started 28 years ago at famous sculptor Daniel Chester French’s home, Chesterwood, in Stockbridge, Massachusetts. The show continued there for three years. With the number of exhibitors and spectators increasing each year, the need for more space prompted the show to move to Eden Hill, one of Stockbridge’s great estates. In 2006, with the desire to add more classes, the show expanded to a two-day show and moved to Orleton Farm. A third day was added in 2011 expanding the show with more classes and divisions for our exhibitors.
We hope you enjoy your weekend at Orleton Farm and wish you all a safe and successful show.