In 1876, as the celebration of the Nation's 100th anniversary approached, a group of 43 citizens decided the best way of demonstrating the town's patriotism was to erect a massive flagpole in the middle of the Main Street where it would dominate the vista seen by anyone approaching the center of town from any of the four cardinal directions.
This first pole was made of wood, built in two sections like a ship's mast, which gave rise to the local folklore that the pole was constructed by ship wrights. From the few descriptions and one photograph that we have, it must have stood between 60 to 70 feet tall, and was positioned directly in front of the Meeting House, just a few feet from its present position. Unfortunately wooden poles and the New England climate are incompatible and 16 years after the flag's raising, it had to be replaced.
The second pole was also of wood and was slated to consist of three sections that in total would rise 114 feet, or about 14 feet higher than the present-day pole. This was deemed to be impractical and the pole was reduced to its original height. New England weather was also unkind to the second pole and in 1905 it was struck by lightening, badly shattering the upper section and burning the flag that was flying at the time. The damaged section was replaced, but the lower portion remained unchanged, despite becoming badly deteriorated.
On Feb. 28, 1912, a heavy wind arose at 2 a.m. and the flagpole snapped off about 15 feet above the base. It fell to the north, almost entirely in the roadbed, missing the Meeting House and any pedestrians who might have been in the area at that early hour.
The stump of the pole remained for two years, until the Men's Literary and Social Club of Newtown Street, in a burst of public service, arranged to raise its replacement in time for the July 4, 1914 celebration The new pole was still wooden, but now rose 100 feet high in two sections. It also proved controversial.
A year before its erection, the State Highway Commissioner issued an edict saying the flagpole was a traffic hazard on the newly numbered state road, Route 25, and must be removed. He had not counted on the influence of the various members of the Men's Club, however, and was forced to relent.
The third flagpole suffered a similar fate as its two predecessors. By late 1949, the lower portion of the upper mast was hopelessly rotten. Replacing this section proved too impractical, because the bottom portion was not in much better shape. But by now the flagpole had become a local landmark – not replacing it was never considered.
On Jan. 20, 1950, the old pole was removed and a few feet south, a large hole – 7-feet wide and 12-feet deep – was dug through the pavement. Into this hole was placed a 21-inch-wide galvanized steel cylinder. Concrete was then poured around the cylinder to hold it firmly in place. The new 16-inch-wide, 100-feet-tall flagpole was then lowered and the gap between the pole and the support cylinder was filled with sand to facilitate its removal in case of future repairs.
This latest flagpole has stood for the past 60 years withstanding weather and traffic accidents. It even survived a fatal automobile crash in 1979 when an inebriated driver struck it going 55 mph on Main Street. The flagpole sustained a dent.
The fatal accident prompted the state transportation department to renew their efforts to remove the flagpole. That effort was disarmed in 1981 when then state Rep. Mae Schmidle, of Newtown, introduced legislation prohibiting the removal of the flagpole in perpetuity.