It sits on a glacial trough, measuring 1.1 miles in length, 4,000 feet in width. In the early years following the Revolutionary War, it was the site for various saw mills, grist mills, and later a mint, operated by Captain Thomas Machin at what was then known as Machin’s Pond. In the 1830s, for reasons that remain unclear, a clergyman named Thomas B. Wilson began referring to the pond as Orange Lake. The name stuck.

In the 19th Century and into the early 20th century, the lake and lakefront became Orange County’s playground. Summer cottages sprang up along the shore. Trolly service between Newburgh and Walden, established in 1895, delivered thousands of visitors to an amusement park that opened on the south shore of the lake.

A year later, the Pine Point Resort was established on the south shore, thriving during the Big Band era, and attracting the likes of Frank Sinatra and Benny Goodman. The casino lasted through the great depression and was closed and demolished in 1953.

The lake remains a sporting paradise for boating and fishing. And when the temperature dips below freezing for an extended period of time, look for a century-old tradition to return to the lake.

Ice yachting has been around for more than 200 years and was popular in Europe around 1800, when the boats first began appearing in the Hudson around Poughkeepsie. Among the sport’s early champions was Commodore John E. Roosevelt, FDR’s uncle, who built the Icicle, described at the time as the fastest yacht to date.

The Orange Lake Ice Yacht Club was chartered around 1880 by a group of local businessmen, including Henry C. Higginson and William H. Smith, notes Historian/Author Patrica A. Favata.

“It held regattas every year and had its own clubhouse,” Favatta wrote in Around Orange Lake. “The strong winds across the lake made it an excellent choice for ice boaters.”
Speed skating and ice skating have also been part of the lake’s history. The National Amateur Speed Skating Association’s races took place there in the early 1900s. Pleasure skating and ice hockey are also commonly seen on the frozen waters of the lake, Favata notes.

With temperatures hovering in the 40s and expected to top out around 50 this weekend, it may be awhile before we see the white sails on the lake this year. Ideal conditions call for frigid temperatures, a strong wind and six to 12 inches of ice on a lake that is free of snowfall. The Old Farmer’s Almanac has predicted a milder-than-normal winter for the early months of 2020, which means that we might have to wait for our next glimpse of the white sails on the lake.