Naples Downtown consisted of a few businesses located approximately 3 blocks east and west of Ninth Street South (U.S. 41), at the junction that was known as Four Corners. Ed Frank's Garage and his small strip mall, the Chamber of Commerce building, telephone company, train depot, a liquor store, gas station, dry good store, Club 41 and not too much else was located there.

Club 41 was a popular place for entertainment. It has been said that among the guests that frequented the Club were Gary Cooper, Lawrence Tibbets, Gertrude Lawrence and perhaps Gloria Swanson.

Occasionally a car would pass by Four Corners. Some were crossing the state going to Miami on the new Tamiami Trail East that had been completed in 1928. At noon you could hear the loud train whistle from the Orange Blossom Express as it arrived daily at the Depot train station just a block away. Today the Depot remains as a historical landmark of the train service that began in Naples in 1927.

In 1923, the Frank family lived upstairs over the Ed Frank Garage near 10th Street South. This was the first commercial building on Fifth Avenue South. Mrs. Frank would throw her table scraps to alligators in the swamp below which eventually was filled in with old cars and motors. This family was one of the first settlers in the area and are noted for having opened the first car dealership. Mr. Frank invented the first swamp buggy and also built the first strip mall.

The first bank in Collier County was built in 1923 in Everglades City. It was 26 years before Mamie Tooke, often called the Mother of Naples, opened the first bank in Naples in 1949 on Fifth Avenue. South. She was instrumental in teaching locals how to budget and save their money, and many of those original depositors became large land owners. In 1989, it became Barnett Bank.

Cory Osceola (a member of the Seminole tribe and local resident of Naples) and his family used to set up a stand and sell their Indian crafts on Fifth Avenue. They were a very well respected, old Indian family in the area. The descendants of the Osceolas are now world-renown builders of Chickees (cypress pole constructions with palmetto-thatched roofs). Today many of their structures stand in southwest Florida and the Caribbean.

The Naples Depot began providing train service on January 7, 1927. The last train to leave Naples was in 1971 when the service was discontinued. The Depot has since been restored and is today used by many community organizations for functions. A train whistle is blown at noon every day just as it was in the early days of Naples.

The Rexall Drug Store on the corner of Fifth Avenue South and 8th Street South was the meeting place of local businessmen. They sat at the benches in front of the store and discussed local business highs and lows each day. No one objected when the children sat on the floor inside reading the new comic books when they arrived. This building changed hands in 1971 and is now known as Naples 5th Avenue Pharmacy.

The Naples Women's Club was responsible for providing Naples with it's first library as early as 1932. In 1951, they built the club house at Park Street and Sixth Avenue South which housed the library and had a separate street entrance.

The location of the Naples Chamber of Commerce has come full circle. In 1928, it was located in approximately the same spot as the Chamber's Visitors' Center of today.

In 1929, a small building housed the telephone company where the Merrill Lynch building is now located. In 1945, there were 17 telephones in town. In 1968, the United Telephone Company built a new telephone building around the first little structure. The counter where telephone bills were paid is now the counter where the chef from Bistro 821 turns out his delicacies.

In the 1944 hurricane, Pappy Turner's cow and calf were loaded on a skiff and put on high ground for safety. That location today is the sight of Kepp's Men's Store. This was also the original location of Wynn's Market in 1945. (The Turner family still owns Turner Marine on 10th Street South.)

In 1960, during Hurricane Donna, surge water was over the table tops of Beroni's Cafe which was located on Fifth Avenue South near 9th Street South.

The first road, of sorts (shells in deep mud ruts), from Naples to Fort Myers was completed in 1918 and is known today as Tamiami Trail North. To travel to Miami one would have to go north to Jacksonville and then south. In 1928, with the vision and resources of Barron Collier, the Tamiami Trail East was completed from Naples to Miami.