Old Fashion Sleigh Riding

When we think of the Berkshires in western Massachusetts, almost everything nostalgic comes to mind. With its rural, yet sophisticated landscape, you can’t help but to find yourself basking in memories of days gone by. This past Sunday, January 16, 2011, many found themselves to be doing just that as the Winter Classic Sleigh Rally was held on the grounds of Orleton Farm in Stockbridge. Stockbridge, best known for their famous artist Norman Rockwell, was indeed the perfect backdrop for such an event with its quaint small town charm and its nostalgic Main Street that is anchored by the infamous Red Lion Inn that warms the hearts of many on a cold winters day. With its fire-place crackling and their chefs cooking up for hearty appetites, the Red Lion Inn is a place everyone should discover.

While the Red Lion Inn is certainly one of the main attractions in town, this past Sunday everyone flocked to the farm to enjoy the sleigh rally as many watched in excitement as horse-drawn sleighs whimsically dashed away through the snow-covered field. This was the eighth sleigh rally that the Colonial Carriage and Driving Society has hosted at Orleton Farm. With the farms splendid mountain views, the farm was the perfect backdrop for the sleigh rally. The rally started off a t 11AM with the parade of sleighs, which was essentially a warm-up session for both the drivers and the horses. Soon after, it was time for the judging classes to begin as the judges judged on everything from the horses manners to the ability of the driver, even a Currier & Ives look was being judged, which was to re-create scenes depicted in the Currier & Ives prints of days gone by.

Participants and spectators of all ages showed up to take part in the festivities as they let their minds wander to memories of yesterday, which is exactly what organizers of the event had hoped to create. One woman said that it may be quite cold, but she couldn’t help but to think of warm thoughts from way back when as she used to be brought to school during the winter in horse-drawn sleighs. Her mother would make sure that she was bundled up in layers as a wool blanket covered her from the elements along the way. Once she arrived to school, she said, she couldn’t wait to head inside to the fireplace where she would warm-up as she lay her winter dressings close by to warm-up as well.

So many others  jogged their memories as well as they stood around a crackling bonfire watching as a parade of sleighs dashed by. Spectators of the event were also welcome to hop on board a horse-drawn sleigh that carried them through the farm. In the Berkshires, just like in Connecticut’s Litchfield Hills, so many of these great events take place as our region is known for rural simplicity of days gone by. Many flock to the hills from the highly urbanized coastal locations to enjoy such splendor, and it is events like these that continue to ensure tourists of all ages come back for more in the future.


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