From 1898-1902, Checotah townspeople invested in the city's future by building impressive red brick Romanesque structures. The block was planned by Mr. W.E. Gentry, known as "The Father of Checotah." The surviving arch was the entrance to Checotah's First National Bank, which opened July 5, 1898, and it is the only original structure that remained after a devastating fire on August 15, 1992. Expansion eastward began in 1898 with the Hutchinson Mercantile, also called the IOOF Building, which also housed the Masonic Lodge and later became the town's only three-story building in 1912. H.D. Kniseley and Co. followed in 1899 as the oldest and largest drug establishment in Checotah. In 1901, the Sherwood and Avery Building included a second floor known as Tuckabatchee Hall, the hub of Checotah's social activities; Tuckabatchee in Creek means "add to and stick together." The building was purchased in 1925 by Checotah Masonic Lodge #86, A.F. and A.M., and its first floor was occupied by Vandiver Hardware from 1940-1991. Three other 1901 buildings completed the block: the Chenault Mercantile, later owned by grocers Vandiver and Blackwell from 1924-1971, Marsh Drug, and the previously razed Checotah Hardware. After intensive study by Checotah Main Street's Arch of Triumph, Inc., local investors formed The Gentry Group, L.L.C. to rebuild commercial space appropriate to the block's 1982 listing in the National Register of Historic Places Business District.