Please Note: The 2022 Coaching Weekend has been cancelled.

The Coaching Weekend has been postponed
until Columbus Day Weekend
October 9, 10, and 11 2026.

Please Note: The Drive For Saturday October 7th, Has Been Cancelled.

NOT YOUR ORDINARY DRIVE THROUGH THE COUNTRY. This will be our twelfth drive, continuing the Gilded Age tradition of Coaching in the Berkshires. The Berkshires, of western Massachusetts, known for its natural beauty and beautiful hillsides, provided a favorite setting for many members of the Coaching Club to drive their coaches and Roof seat breaks in the Berkshire hills. The Coaching Club members included Augustus Schermerhorn, Harris Fahnestock, George Griswold Haven, Sr. and George Griswold Haven Jr., Harry Payne White and Coaching Club president Frank K. Sturgis all had residences in the Lenox area.

They came to enjoy the perfect fall weather and the glorious foliage throughout the rolling hills. The Astors, Vanderbilts, Fields, Morgans, Carnegies, and Westinghouses were some of the famous families that built large opulent “Cottages” and the Berkshires became known as the “Inland Newport”.

We encourage you to view the horses as they travel the roads of the Berkshires, going to Highlawn Farm on Saturday October 10, arriving at approx. 11:15 am, Sunday they will travel to Edith Whartons the Mount and arriving at approx. 11 am and Monday the horses will travel through the lovely village of Stockbridge on their way to a private estate and back through Stockbridge to Orleton. Be sure to check the web site daily as all routes are subject to change because of weather and road conditions.