Built in 1790, the James Pharmacy originally served as the general store for the Humphrey Pratt Tavern and formerly stood adjacent to the Humphrey Pratt Tavern at the corner of Main Street and the Old Boston Post Road. It was moved to Pennywise Lane by a team of oxen in 1877. Humphrey Pratt was the brother of Deacon Timothy Pratt, who lived in the house next door, The Deacon Timothy Pratt Bed and Breakfast.

Over the years the building gained attention as the place where Lafayette made a purchase when he returned in 1824 to America on a triumphal tour and visit with old Revolutionary War friends. Evidence of his purchase seems to be lost and various stories claim that he bought wool stockings, or gloves, or saddle soap. The sign proclaiming his unknown purchase remains attached to the building as a unique and enduring advertisement.

Peter Lane and his wife Bertha moved to Old Saybrook in 1895 and rented the property, establishing the town’s first pharmacy. Peter Lane added the soda fountain portion of the pharmacy in 1896.

In 1902, Peter Lane's sister-in-law Anna James came to work with him at Lane’s Pharmacy, and lived there with the rest of the Lane family. She graduated college in 1908 — the first African American woman to graduate from the Brooklyn College of Pharmacy.

When Peter was called away to fight in World War I, in 1917, he left the care of what was then the Lane Pharmacy with his sister-in-law, Anna Louise James. “Miss James” – as she was known to the community – changed the name to “James Pharmacy” and set about making improvements to the building. In 1922, she added a two-story wing and the pharmaceutical motif on the front of the building. In 1925 she installed the display cases and glass-door cabinets, manufactured by the L.F. Dettenborn Woodworking Company of Hartford. In the early 1930s, architect Francis Nelson re-designed the building, adding the ice cream parlor with the arcaded front extension.

Today this historic building has been lovingly renovated, while the Gelateria honors its ice-cream legacy.