1922 October 25
Sarah D. Perkinson was appointed and commissioned as first Postmaster of Cherry Grove by Hubert Work, Post-master General of the United States of America, on Oct. 25, 1922. Formal mail service is believed to have begun in the early summer of 1923. The mail was received at the Perkinson Hotel. Sarah Perkinson held her commission for eight years, but because of declining health others assisted or took over the postal duties. One summer, hotel operator Joseph Levy, of Sayville, assisted with the mail.

1927-1930
Anna (Jost) Stein, served as Postmaster. Mrs. Stein initially received mail at the Perkinson Hotel and later at her home on Fire Island. She may have served through 1931. Records are unclear.

1929 July 04
The Great Airplane Speedboat Race of 1929 pitted velocity in the air against horsepower on the water - the faster claiming superiority as a means of transporting mail from the mainland to the beach.

Fremont Abrams was at the helm of his "Hacker" powerboat. Bill Hunt was powering "Patchogue Wings," Suffolk Flyers' new Curtis engine bi-plane. The objective was to deliver an official sack of U.S. Mail from Patchogue Post Office to the Post Office at Cherry Grove. Each sack contained 1,750 pieces of specially stamped mail. The airplane won the race just shy of fifty seconds faster than the boat. As a result of this race, the first (and only) air mail delivery to Cherry Grove occurred.

1932 September 16
Nelson D. Warner was nominated as Postmaster at Cherry Grove, on Fire Island Beach in 1932. Cherry Grove was one of the smallest Post Offices on Long Island. It was expected that Warner's nomination would be approved, as the position was not greatly sought after and was considered far removed from being in the political plum classification.

1933 February 25
Nelson D. Warner became the 3rd Postmaster of Cherry Grove. He was appointed and commissioned by Walter F. Brown, Postmaster General of the United States of America, on Feb. 25, 1933. "Captain Warner," as he was referred to, brought the mail to the Grove Islanders on "The Edward," a vegetable boat delivering perishables and newspapers along with the morning and evening mail. The goods were delivered to the Cherry Grove Market located on the Cherry Grove Boardwalk where you now arrive at the Cherry Grove Dock.

1938 September 21
The Great New England Hurricane's storm surge repositioned Warner's store to where it sits today, on the south side of Bayview. Warner left the repositioned building there. It is believed that between late 1938 and 1945, the corner 'bump-out' (which is today's Post Office) was added, connecting to the store. Today's Post Office location was not in the 'bump-out' until 1967.

The Post Office located in Warner's Cherry Grove Market, was open from July 1st to Sept 1st with two mail deliveries a day, morning and evening. The mail was later carried by the ferry between Sayville and the beach. The "Captain" died in 1944, and the village Post Office that he operated out of his Cherry Grove Market was closed.

1944
When he found the Federal Government was paying only $43 a year for rent, Alfred V. Lehman, new owner of the Market, felt he could better use the space taken up by the Post Office, and he ousted the postal service. He asked that the equipment be removed.

1945 May
On learning of Mr. Lehman's decision, the Post Office Department issued an ultimatum in May that "unless new Post Office quarters were obtained by June 1st, 1945, the start of the season, the Cherry Grove postal unit would be discontinued." There was also an article in the Suffolk County News: "Postmaster Wanted at Cherry Grove, on Fire Island Beach. The Post Office is a fourth-class office, open each year from June 15th until October 1st. The salary of the Postmaster depends on the amount of business transacted."

Mrs. Anna (Jost) Stein, was appointed acting Postmaster of Cherry Grove and served from 1945 to 1949.

Anna Stein had been Postmistress from 1927-1930, assisting at the Perkinson Hotel. She took over the duties again as acting Postmaster in the Post Office which was being built to meet the Post Office's deadline, which had been declared by the United States Postal Service. Mrs. Stein's son, Ken Stein Sr., who ran the ferry from Sayville to Cherry Grove and was also a mail messenger carrying the mail between Sayville and the Great South Beach resort, undertook building a new Post Office before the deadline. He purchased a small triangular parcel from Marion Per-kinson of Patchogue which was bounded by three walks- Main, Cherry Grove and Bayview. Ken Stein Sr. built the tiny new building on the 306 square-foot triangular space, in order to keep the Grove's 4th class Post Office rating.

According to Ken Stein Sr., he delivered the mail from Sayville to Cherry Grove for $140 a year (it went up to $400 in 1945). He did that for 60 days a year, 12 times a week from July 1 - September 15 and six times a week, June 1 - June 30. Today, delivering the mail from Sayville to Cherry Grove is so much more costly!

Harry T. Weeks of Patchogue, summer resident of Cherry Grove, had submitted Ken Stein Sr.'s application for a building permit to Town Building Inspector, Emil Lange, late in May. Because the plans for the structure were in violation of the zoning ordinance, Mr. Lange advised Mr. Weeks that approval would first have to be obtained from the zoning appeals board. The front yard requirements were not met, and the building covered well over half of the plot, which was above the limit prescribed by the ordinance. Unfortunately, the appeals board would not meet again until June 14th, which would be beyond the June 1st deadline. Ken Stein Sr. constructed the Post Office building anyway, completing it before the deadline of June 1.

1945 June 01
Postal service for Cherry Grove began on this day in the first official Post Office building opening the doors with Mrs. Fred (Anna) Stein as Postmaster. The post office planned to operate that year until September 15.

The building which was to be used exclusively for the United State mail was well-constructed with white shingles, green trim and a blue roof. It fitted snuggly into the triangular sand strip between boardwalks on the bayfront. It drew much admiration from Cherry Grovers. However, Ken Stein Sr. was served with a summons for zoning ordinance violations.

1945 June 14
According to an article in a local paper, Cherry Grovers turned out 70 strong to attend the hearing of the Brookhaven Town Zoning Board of Appeals in the Town Hall in Patchogue. They were delighted when the board granted a variant of the zoning rules to permit the Post Office built by Kenneth Stein Sr. of Sayville to remain where it was then situated. There was no opposition. The argument was made that public necessity required the building of a post office in short order to prevent the postal authorities from taking the Post Office away from Cherry Grove. Ken Stein Sr.'s building met the requirements of the building code except that it was not set back from the side lines.

When the board's chairman, Joseph Corbett, announced its decision, many of the Cherry Grovers applauded loudly. The building inspector, a Mr. Lange, said that in view of the board's approval in granting the variance applied for, the court action would undoubtedly be dropped. The construction did meet all requirements of the zoning code.

1946 June 27 - 1947
George Peet Gerrodette, son of Irene Peet Gerrodette was commissioned by Robert E. Hannegan to serve as Postmaster at the Cherry Grove Post Office. His tenure lasted one year.

1949 October 21 - 1967
Irene Peet Gerrodette was commissioned as the new Postmaster at Cherry Grove by Jesse M. Donaldson, Post-master of the United States of America. Irene Peet Gerrodette was upset that the public referred to her as a Postmistress. She always insisted that she was not a Postmistress; she was The Postmaster. She served until 1967. Before the Community got electricity and telephones, the only phone in the Grove was in the hotel. All communications went directly to the hotel. In order to receive your messages, you had to go to the hotel to pick them up. Irene Peet Gerrodette had a phone installed at her home on Lewis Walk, named "Dune Top". She could then receive the telegrams over her own telephone and have her grandson, Bob, or granddaughters, Sally, and Gerrodette (Gerri) deliver them.

1949-1950
While Irene Peet Gerrodette was Postmaster of the 4th Class Post Office in Cherry Grove, her granddaughter Sally started helping out. When she was 11 or 12 around 1949/50, she delivered telegrams and special delivery letters. Years later, she progressed over time to all the other duties, including processing incoming and outgoing mail, selling stamps, money orders and bookkeeping for one year. One year when her grandmother took a two-week vacation, Sally became Acting Postmaster.

During these years the former Lone Hill Coast Guard Station land was developed and became the Fire Island Pines. Lots were sold, and the growing Pines community needed a Post Office too. Until they could get their own, they came to Cherry Grove for their mail. As Postmaster in Cherry Grove, Irene Peet Gerrodette was put in charge of getting the Pines Contract Station operational. She sent Sally to train Arden Catlin who then ran the Post Office Station out of her real estate office.

Plenty of famous and infamous persons summered in Cherry Grove. Sally well remembers getting and sending mail for Truman Capote before he moved to the Pines. It had been thought Sally would be the next Postmaster, but she moved to San Diego in 1956, and that duty went instead to her mother, Irene Peet Gerrodette's daughter, Jeanne Skinner.

Irene's daughter Jeanne Skinner had assisted her mother over the years and won the Contract Station Postal Clerk position that she applied for.

The original Post Office building faced the Bay to the north (1945) and later was repositioned to face west (probably where the Top of the Bay's staircase is today). Some photos show the Post Office building at that time (1958) to have been painted red. Postal Service was then moved to the Cherry Grove Market building around 1967. The new Market owner, Judge William Underwood, had expected a substantial rent for housing the Post Office. Disappointed by the amount (which was paid by whoever was running the Post Office out of their own salary), he had wanted the Post Office to vacate. However, to this day the Cherry Grove Contract Station remains at the Underwood's location, at 161 Bayview Walk, P.O. Box 4006.

1957
Cherry Grove Community finally got electricity and telephones.

1962
Joseph Pokorny purchased the Stein's Ferry Service. The Pokorny's became the operators of the Island Ferry Corp. which serviced the Grove for 20 years. Their service was then bringing the mail to Cherry Grove.

1967-2009
When Irene Peet Gerrodette died in 1967, at 75 years young, the original status of the 4th Class Post Office was retired and changed to become a substation out of Sayville.

Jeanne Skinner was the Clerk in Charge of the contract station in Cherry Grove. Clerks in Charge could do everything except issue money orders. Jeanne received a flat fee for six months, from May to October. She lived at her home called "Beachhome" on the ocean and could be seen walking to the ferry for the 10 a.m. mail pickup and returning to the ferry for the 2 p.m. send off, six days a week.

She served as the infamous mail lady for Cherry Grove for over four decades. It was thought that in the quiet times at the Post Office she might have thumbed through box-holder magazines not yet picked up, or perhaps even glanced at their incoming postcards. Some residents of the Grove chose to receive post cards written in French, believing that no one else could read them. Later Jeanne divulged that she was able to read French. Surprise, surprise!

1982
The Stein family bought back the Ferry Service and have served the Grove and Fire Island Pines to this day.

2009
Jeanne Skinner passed on July 3, 2009, at 92 years young.

Jeanne holds the record as "Longest Serving Mail Clerk in Charge of the Cherry Grove Contract Station out of Cherry Grove" for 42 Years!

2009-2011
Various people kept the Cherry Grove Station up and running in the two years following Jeanne's death. Those included Fire Island Pines Clerk, Gene Cook, and the Grove's own Tim Webster and Daniel Craig.

2011 to the Present
Elizabeth (Betty) Faraci took over as Clerk serving the Cherry Grove substation.

Betty had worked for the Sayville Post Office from 1982 to 1984, first as a mail carrier, then as a clerk. She retired from the postal service after 22 years. When Jeanne Skinner was in charge of the Cherry Grove station, Betty often worked with her when Jeanne went to the Sayville Post Office. Paul Achenback, Postmaster of the Sayville Post Office, called Betty, in 2011, and asked her if she would consider coming back to work as the Cherry Grove Clerk. She said yes, and has been greeting the Cherry Grove community, as well as our four-pawed friends, four days a week for the last twelve years.

Mail service has changed recently with the ability for customers to send packages to our Post Office. Receiving only mail and magazines is becoming a thing of the past. One day last year, the Cherry Grove Substation received six bags of mail, containing seven bundles of letters and magazines, as well as 50 to 60 boxes of various sizes. Due to the volume of mail and especially packages, Betty has been assisted recently by community volunteers, including Lorraine Michels, Irma Ruiz, Alison Brackman and Paulette Manos. The newest addition assisting at the Post Office is, Paulette's niece, Sienna Hartman.

Cherry Grove has 32 original mailboxes which are considered antiques. 142 replacement indoor mailboxes were installed during Jeanne Skinner's reign totaling 174 working mailboxes inside the building. With many new Cherry Grove residents, the Post Office had to install 48 outdoor keyed mailboxes last year. Therefore, the Cherry Grove Post Office has 222 mailboxes.

Thus, the remarkable 100 Year History of the Cherry Grove Postal Service continues to be a source of pride to all of us who value and appreciate this outstanding and vital service.