History of the famous Colebrook flagpole

It no longer stands, and indeed the very location has all but been forgotten, but Colebrook once boasted the largest flagpole in the state. When you hear superlatives such as this, there is always a little voice in the back of your head that reminds that there might well be a larger one somewhere, perhaps the one in front of the state capitol, that had escaped the attention of the raisers, isolated as they were up here in the hills. However, in this case, my guess is that they might well have been correct, because by use of semantics, “largest” doesn’t necessarily mean “tallest,” and the sheer mass of this flagpole places it in the category of several tons.We don’t have nearly as many as I would like, but the Colebrook Historical Society has several old picture postcards in its collection, and one happens to show this flagpole, although it is not identified as such. The card was produced by W. W. Cooper, who, at the turn of the 20th century was Colebrook Center’s postmaster as well as the proprietor of a store in his home located at 474 Smith Hill Road, next to the old Colebrook Inn and across from the Green in front of the Congregational Church. The view is of Colebrook Center taken from the top of the field in back of Jake and Tara Thompson’s at 1 Thompson Road, in back of the church. The heyday for American postcards began during the last decade of the 19th century and began to decline about the time of World War I, although they never ceased to be popular and still are very much in circulation.On the right-hand side of this photo is an outbuilding and roof of the house now identified as 467 Smith Hill Road. Next are several large buildings that were barns and their associated outbuildings, belonging to Lester Smith. The barns nearly at the center belonged to Ray Oles, who lived and farmed what is now 1 Thompson Road. Dimly seen through the trees directly over these roofs is the steeple of the Congregational Church. Farther left can be seen the Colebrook Road, and west of that are the buildings associated with Rockwell Hall, or 549 Colebrook Road today. To the left of them is a vertical white stripe — this is the Colebrook flagpole. Note its location along the western edge of the field behind 1 Thompson Road, near Colebrook Road.To the left of the flagpole can be seen what was then the brand-new structure of 569 Colebrook Road, and next to it 579 Colebrook Road. The horizon is dominated by Mount Pisgah, with several fields associated with North Colebrook appearing behind the flagpole.The flagpole was raised on June 8, 1907, and was touted as the largest flagpole in the state. It was the brainchild of Raymond Oles, a Colebrook Center resident, who was also responsible for its construction. It was the general consensus of residents then that the raising of this mammoth pole would be one of the crowning events in the history of the town and would, for years to come, attest to the patriotism of Mr. Oles and several other lifelong citizens.The Old Glory bearer was made of two enormous trees consisting of a hemlock butt measuring 2.5 feet in diameter that had been cut in Goshen about two years previous to the raising and had been hauled to Colebrook after two attempts, by four horses. The top section was of chestnut and had been cut on the farm of Eugene Twining, another resident of Colebrook. The overall length was 85 feet, and it was to be 75 feet tall when planted in the ground. The total weight was estimated to be approximately 5 tons.The two sections were spliced and the scene was set for raising. It was proposed the pole would be erected in celebrating Memorial Day 1907.However, despite the fact that 125 men volunteered their pole-raising services and strength, efforts proved to be futile. Two pair of oxen drew the pole to the site where a large staging had been erected along with a 40-foot propping pole. The monstrous flagpole proved to be too awkward and heavy for even this many men, and along with the fact that the propping pole came crashing to the ground, the raising was not accomplished on this first try. It was decided to engage the services of contractor A. H. Hubby of Winsted to sink the pole.On June 8, a Saturday, the contractor, together with the aid of four men and a capstan, were successful in raising the large and impressive liberty pole. It was erected on the Oles property, located just south of the Congregational Church, and shortly thereafter, Mr. Oles proudly unfurled his handsome 40-by-26-foot 46-star American flag. Bob Grigg is the town historian in Colebrook.