As runners pass through the gates of Whitehall, the estate of the White family, they will soon enter the race’s fifth mile. The slight downhill grade provides a respite for these runners, who will soon enter the Microwave Mile and face Gallows Lane. This wooded environment was the heart of the estate.

The Windmill Hill windmill (From Rachel Carley, Litchfield: The Making of a New England Town

There are many vestiges of the past splendor of these grounds. The shingled building to the right was the family’s carriage house. From here, they traversed the miles of carriage roads that crossed their thousands of acres. The hill behind the carriage house is Windmill Hill, so named for the wind-powered pump that filled a cistern to provide water to the home. This hill was also the site of exotic tree plantings by the family, who planted over one million trees on their estate.

Whitehall (Courtesy of White Memorial Foundation)

The current visitor’s center was Whitehall, the seat of the estate. John Jay White moved his family here following the New York City draft riots in 1863. Alain went on to study botany at Harvard, and became a master chess player, a skill that led to his recruitment as a cryptographer during World War I. May’s philanthropic spirit centered on bringing children from New York City to Litchfield for summers. The family home was designed in quintessential Victorian style, with garrets, a tower, and many chimneys. The structure underwent extensive renovations when it became the center of the White Memorial Foundation.

Note the tree stump on the right side of the image. (Courtesy of the White Memorial Foundation)

Across the street from the visitor center is a concrete tree stump, a reminder of earlier days when this area was the scene of picnics and even duck pin bowling, on an alley painstakingly leveled by Alain White for the use of the Sanctum club.

Chickadee Bridge (Courtesy of White Memorial Foundation)

A notable feature of the race for runners is crossing the Bantam River on the Chickadee Bridge. This bridge allowed the Whites to access their carriage roads on the east side of the river. The shoreline is now covered with trees, rendering this view impossible. The Whites often called this Silver Bridge, and noted that it was the farthest up the river that motorboats could venture; today, the presence of beaver dams makes this also impossible. The Chickadee Bridge stands as a reminder to runners that while they here turn back toward Litchfield, their journey is going to get much more difficult.

For more information on the history of the Litchfield Hills Road Race, see Lou Pellegrino’s book A History of the Litchfield Hills Road Race: In Smallness there is Beauty (now available).