E. N. Bailey: 

Frontiersman First Selectman

E. N. Bailey was no ordinary first selectman. He “surprised some and frightened others by arriving frequently in the village with large copperhead snakes twined around his neck and shoulders,” The Ridgefield Press reported at his death in 1955. “He wasn’t afraid of them and gave the impression that he wasn’t afraid of anything else either.”

Eldridge Nettleton Bailey was born in Shelton in 1876. Usually called “E.N.” or “Bill,” he came to Ridgefield at the turn of the century to work for Henry B. Anderson who was then developing his vast estate on West Mountain, now the Eight Lakes Estates (Anderson is also profiled in Who Was Who).  Bailey was a construction engineer, and supervised the building of Anderson’s roads as well as the Anderson mansion on West Mountain. “He was a tall man, carried himself erect, walked with great strides, and wore the striking clothes of a frontiersman,” said Karl S. Nash, Press publisher, who knew the man.

Bailey became head of the Ridgefield Water Supply Company, largely owned by Anderson, as well as Anderson’s Ridgefield Electric Company. 

However, he was better known for his political career. Bailey was elected first selectman 11 times. The post was then part-time, and the term, one year, and he held the job most years from 1911 to 1926. But now always.

His political career began in 1910 when he was elected to the Board of Selectmen to serve with Benjamin F. Crouchley, a rare Democratic first selectman. The next year he defeated Crouchley for first selectman, but lost in 1912 to Charles B. Northrop. He returned to power in 1913, and was re-elected in 1914 and 1915. Orville W. Holmes then won the Republican nomination in contests with Bailey for three years in a row, but Bailey did not give up, finally winning the job back in 1919 and holding it until 1926 when Winthrop E. Rockwell was the victor “in a memorable party battle in the town hall,”  Nash recalled. Rockwell went on to hold the job for 20 years — Bailey tried once to return and failed.

He was “a force in Ridgefield affairs and remained a controversial figure throughout his public life,” Nash said in Bailey’s obituary. 

Bailey was a director of the Ridgefield Savings Bank, now Fairfield County Bank. He and his wife, Lois, sang in the First Congregational Church choir. He also tried his hand at amateur theater, which led to a bit of a scandal. In rehearsing for a play in the 1920s, he fell in love with his leading lady, Miss Nina Olmstead. He and Lois were soon divorced and Bailey married Miss Olmstead. The two moved to a farm in Bradford, Vt., but, according to Nash, “his marriage foundered and he returned to Ridgefield and spent his declining years at The Elms Inn.”

He died in 1955 at the age of 77.

Henry B. Anderson: 

A Man of Land and Utility

An 1895 fire destroyed most of Ridgefield’s business district. One of the big problems when the blaze broke out at corner of Main and Bailey was lack of water to fight it. 

That prompted villagers to create a water system that began operation in 1900. Spring fed and financially unstable, the system proved inadequate until Henry B. Anderson took over.

With his help, Ridgefield entered the 20th Century with both village water and electricity.

Henry Burrall Anderson was born in New York City in 1863. He graduated from Yale in 1885, went to Harvard Law, and wound up a top industrial attorney in Manhattan, with such clients as the New York Central Railway. He had many interests, including serving as president of the Automobile Club of America (succeeding Elbert Gary, the steel magnate for whom the Indiana city is named) and working with the Charity Organization Society, which tried to break the “cycle of poverty.”

In the late 1800s Anderson built a summer home off West Lane in Ridgefield, using it a few years before selling it to Frederic E. Lewis, who enlarged it into a castle-like structure he called Upagenstit; the estate is now the Ridgefield Manor subdivision.

Anderson built a second mansion on West Mountain, just across the line in Lewisboro, N.Y., overlooking Lakes Waccabuc, Oscaleta and Rippowam. Here he lived with his wife, the former Marie Larocque. However, when his wife died in 1903, he abandoned the house, which eventually fell into disrepair and was razed.

Meanwhile, over his years here Anderson had been acquiring land on West Mountain and Titicus Mountain, winding up with some 3,000 acres; at least 600 acres were in Ridgefield and the rest in North Salem and Lewisboro. 

Anderson hired Eldridge N. Bailey, later a first selectman, to supervise building a network of roads through his property, with the expectation someday of selling sites for fancy summer homes and woodland retreats. His partner in this enterprise was Ogden Mills, secretary of the treasury under President Hoover. 

He also established the Port of Missing Men, a resort/restaurant on Titicus Mountain in North Salem with a spectacular view of the countryside. 

Many Ridgefielders, especially Italian-Americans, were involved in building the roads and operating the Port of Missing Men.

With homes and so much land here, Anderson took more than a passing interest in the Ridgefield community and its welfare.

A small water company had been established, laid pipe, and started operating in 1900, but almost immediately began having difficulties supplying water. “It was not financially stable and had not the capital to prosper and give the town an adequate system,” The Ridgefield Press reported.

Two years later, when he saw the problems the town was having with getting decent water service, Anderson bought the Ridgefield Water Supply Company  and immediately set about improving it, primarily by buying Round Pond on West Mountain to use as its main water source and building a standpipe on Peaceable Ridge to maintain pressure.

The water supply needed electrical pumps so Anderson established the Ridgefield Electric Company to serve not only pumps, but also villagers’ homes and street lights.

Anderson sold his controlling interest in the water company in 1928, and through several subsequent sales, it is now part of the giant Aquarion corporation. The electrical company continued for some years under different ownership until it was absorbed by a regional power company.

During World War I, Anderson offered his yacht, Taniwha, to the Navy. It was commissioned the USS Taniwha and was a Naval vessel from from 1917 to 1919. Anderson was at first placed in command and assigned to patrol the New York Harbor area, but he later worked in the office of the Chief of Naval Operations in Washington until the war ended. 

In his later years, Anderson spent little time in Ridgefield, though he still owned much land here. He had homes on Park Avenue in New York and at Sands Point, Long Island, when he died in 1938 at the age of 75.