The History of The Park Avenue Inn

This historic home, known as the Chittenden House, was built between 1837 and 1839 by Captain R. A. Shine. The house is believed to have been built from materials taken from the original territorial capitol. In fact, the huge multi-paned windows in the entrance, front living room and two septagonal rooms were used in the original territorial capitol, granting the house a special place in the history of Tallahassee.

In 1847, the Inn changed ownership through the purchase of a Louisiana lottery ticket. The night before the lottery drawing, Mr. F.H. Flagg and Mr. Dick Wilson were returning on horseback from playing cards with Capt. Patrick Houston. As the two men rode up Gadsden Street beside the house, which was for sale, Mr. Flagg remarked that he held a lottery ticket for the exact amount being asked for the house and if his number was chosen, he was going to buy it. The next day Mr. Flagg was notified that he had in fact won the lottery, and he and his wife purchased the house.

The home was sold in 1884 to Hattie W. Dickenson and was purchased by Simeon D. Chittenden in 1894. Chittenden added the mammoth Dutch-style front door with its brass handles, latch and lion-headed knocker. He also installed the monumental floating staircase.

The stones that form the front steps and wall along Park Avenue and Gadsden St. had been used as ballast on a sailing ship from Scotland. Chittenden brought the stones up from the St. Marks River and shipped them to Tallahassee on flatcars by the CT&G Railroad.

The home returned to the Flagg family when Annie Maxwell Rawls, the daughter of William A. Rawls and Mary Maxwell (Flagg) Rawls, married Dudley Frisbie Chittenden, Simeon Chittenden’s son.

The home, which has been owned by the same family for 157 years, has served as a boarding house and popular dining spot for Tallahassee legislators.

The present owners are the four children of Mr. and Mrs. Flagg Landon Chittenden, who are the fifth generation of Flaggs to call 323 E. Park Avenue home. Kate Bruner, the Innkeeper, restored and re-opened the home as a bed and breakfast in March of 2015.

To schedule a tour of the Inn, please contact [email protected] or call 855-236-0262.