Railroad Postmarks of the United States 1861 to 1886 by Charles L. Towle and Henry A. Meyer
The U.S. Philatelic Classic Society, Inc. 1968

RPO Railroad Markings: RAILROAD POSTMARKS OF THE UNITED STATES 1861 to 1886, Charles L. Towle & Henry A Meyer
THE UNITED STATES RAILWAY POST OFFICE POSTMARK CATALOG 1864-1977, Charles L. Towle  & Fred MacDonald
U.S. Route and Station Agent Postmarks, Charles L. Towle
Website: www.postalhistory.com/State/New_York/index.htm

LIRR cancellation: July 31, 1858+  cut-square Scott 26-Type III  3˘ Washington TYPE III (#26) Issued: September 14, 1857
has outer vertical frame line on both sides which are not broken between stamps. Charles L. Towle 112-B-1

LIRR RPO Scott #11 3˘ 1851-1857 issue - Cancellation: 12/21/1852 Charles L. Towle 112-B-1

LIRR RPO Scott #11 3˘ 1851-1857 issue - Cancellation: FEBR (Feb.) 10th, 185x?
Towle Catalog No. 112-B-2 R-5

LIRR RPO 1857+

Cover with 3˘ Scott 25,26,26A series of 1857-61 Cancellation is: LONG ISLAND R. R. with DEC 17.  Postal rates in effect at the time:  1855 up to 3,000 miles per 1/2 oz. 3˘ and after March 3, 1863 .06 first ounce (.03 for 1⁄2 oz)

This is Towle Catalog No. 112-B-x used primarily in the 1850s-60's and a very early LIRR cancellation.
I would date this cover as Dec 17th, 1857+.

As no LIRR rail service to Sag Harbor existed prior to 1/1871, this item was carried via the LIRR RPO service as indicated below.
 

U.S. Mail and Norton's Express was carried via the LIRR from Brooklyn to Greenport starting in 1848, then via the steamship "Statesman" which ran regularly between the LIRR's Greenport dock to the Sag Harbor loading docks.  Hence, the LIRR RPO cancellation, but no rail service into the actual town.  At the time of this mailing (1857+)  Norton's Express had been replaced by Corwin & Munsell's Long Island Railroad Express, also known as Corwin & Munsell's Long Island Express, and the same delivery arrangement was in force.  When the LIRR constructed a branch from Manorville on the Main Line to Sag Harbor in 1869, mail and express were no longer carried by ferry from Greenport, but directly by rail.  Express was handled by various express companies which came and went and postal workers handled the U.S. Mail on board trains. Info: Dave Keller from Bruce H. Mosher's, "Express Businesses that Operated over the Long Island Rail Road System."

LIRR RPO 3˘ Scott #65 1861+ as earliest known use: August 18, 1861. Towle 112-C-1 LIRR rectangular negative cancel

Postal rates: 1855 Up to 3,000 miles per 1/2 oz.  March 3, 1863 all U.S., per 1/2 oz.

On April 12, 1861, the war erupted at Fort Sumter. Less than two months later, the United States discontinued postal services to the South. The process of demonetizing rendered the old stamps invalid, while at the same time replacing them with the newly designed stamps. The new 1861 stamps were sent to post offices along with a notice that required an exchange period of six days be announced in local newspapers. During the exchange period, old stamps could be exchanged for new ones. After the six-day exchange period, the old stamps were no longer accepted as postage. Info: Wiki

LIRR RPO Scott #210 2˘ usage rate 8/29/1884  Greenport to Holbrook
Fred Wreden Flour ad envelope - Yaphank, NY
Towle 112-G-1 II LIRR cancellation

LIRR RPO Scott #267 2˘ carmine Type III 1895 issue  Sag Harbor Branch
(Sag Harbor & NY) 7/28/1898 Photo/Archive: Dave Keller

LIRR RPO 2˘ stamped envelope Scott #U395 GREENPORT & NY  - 5/14/1906 Towle 112-N-1
Backstamped to East Marion, NY.
 

LIRR RPO 1˘ postal card Scott #UX18 GREENPORT & NY - Train #10 westbound 10/23/1906

The LIRR 1903 timetable indicates WESTBOUND LIRR trains in the early 1900s were even-numbered.  Not odd-numbered as they have been for decades.  ALSO . . . double digit train numbers were Main Line trains.  Decades later they were Speonk and Montauk trains.  So that changed as well it would appear.

Train #10 was the westbound mail train which left Greenport at 2:40 pm and arrived at Riverhead at 3:26 PM (per timetable), where the mail from the County Clerk's Office would be loaded on board the train.

How did this card get to Patchogue the same day it was mailed, arriving at 4:30 pm (one hour and 4 minutes later) per the receipt cancellation issued at Patchogue? Perhaps that mailbag was off-loaded at Medford and carried by horse and wagon along Patchogue-Port Jefferson Road into Patchogue?  That's a distinct possibility.  It didn't get carried into Jamaica and then back out again on an eastbound train.  Not sufficient time to do so and no additional eastbound RPO cancels added. Info/Archive: Dave Keller

LIRR RPO  Scott 331 1˘ McKinley postal card -  Port Washington & LI City  7/30/1909
Archive: Dave Keller

LIRR RPO Scott #332 2˘ - Wading River & LI City  Train #635 5/15/1912

LIRR RPO  Scott UX27 1˘ McKinley postal card -  Port Washington & N.Y. Train #432 3/31/1934

LIRR RPO  Scott UX27 1˘ McKinley postal card with timetable on back
Port Washington & N.Y. Train #432 3/31/1934

LIRR Scott #551 Nathan Hale 1/2˘ RPO NY & Far Rockaway Train #1067  10/01/1930

LIRR RPO Scott #802 3˘ Virgin Islands - Oyster Bay & N.Y. Train #514  2/21/1938

LIRR RPO  Scott 790 1˘ Naval Issue -  N.Y. & Far Rockaway. Train #1067 4/21/1938
Archive: Dave Keller

LIRR RPO  Post Office Department Official Business -  Greenport & N.Y. Train #211  6/22/1939

LIRR RPO  Scott UX27 1˘ McKinley postal card -  Montauk & N.Y. Train #27  11/40/1943
Archive: Dave Keller

LIRR RPO  Scott UX46 3˘ Greenport & N.Y. Train #211  8/09/1961
Archive: Dave Keller

LIRR Claim Department envelopes 

Cover with 2˘ Washington LIRR perfin stamp cancelled July 18, 1913 
Notation: 'Called & wrote Mrs. J on 8th August 1913'

LIRR Claim Received Postal Card Notice 

Scott UX27 Postal Card front: Cancellation: NY Penn Terminal Station 7/19/1915

3˘ usage rate 9/16/1933 

       LIRR Important Freight Arrival Notice envelopes  

Cover with 2˘ John Adams (Scott #806) PRR perfin stamp used by the LIRR to advise of freight arrival. Interesting as the first class letter rate from 1932 forward was 3˘. The 2˘ rate would apply when the letters were sent unsealed  3/11/1941

Sent from L.I. City to the Fasoline Monument Co, Woodside, NY. As this consignee had no LIRR freight siding location, it would have been a shipment delivery pick-up at a near by team track.

Another example of the 2˘ usage rate 4/5/1940

 Scott UX9 Jefferson Postal Card: 1893 LIRR Form 121 Freight Pickup Slip

9/12/1893 Bushwick - "Please give this disposition for car 1355. 
Cannot send it to Smithtown "Board of Health" restrictions.  Please advise at once."

"

2/17/1894  Bushwick - "Please send check for car (sic) manure 1115 to C. R. Buffett,
East Northport for $1225 and oblige."

Shipping Receipt  IRS Documentary Stamp Scott R163 series 1898
LIRR Form 21 consigned to Winfield 10/02/1899 Archive: Dave Keller

New York World's Fair - R.P.O., First Day of Issue, and  World's Fair Station Cancellation

The New York World’s Fair, featured on U.S. #853, was the largest World’s Fair ever. The stamp showcases the “Trylon” and “Perisphere,” two of the most famous images of the Fair. Over 44 million people attended the fair.

The Trylon was a 700-foot-tall spire that was connected to the Perisphere – a sphere with a diameter of 180 feet. Their images were issued on U.S. #853 on April 1, 1939, but were open to the public later that month at the Grand Opening held on April 30. The Perisphere housed a “world of tomorrow” model city that could be viewed by visitors on a moving walkway.

On April 30, 1939, a very hot Sunday, the fair had its grand opening, with 206,000 people in attendance. The April 30 date coincided with the 150th anniversary of George Washington's inauguration as President in New York City.  Scott #854

Mr. Hyde used this Washington 3˘ pre-stamped envelope (sold until 1932), added the World’s Fair stamp for the postmark at 9:00AM at World’s Fair Station.

Then crossed out the Fair Station address, went and purchased/added the 150th anniversary of George Washington's Inauguration as President in New York City first day of issue stamp with the 11:00AM R.P.O. post mark and RMS (Railway Mail Service) “killer cancel” as utilized for RPO mail for forwarding to his Plainfield, NJ home.

Of course, when applying the additional 3˘ 1939 World's Fair Trylon-Perisphere stamp, it was already in excess rate; referred to as "Philatelic”, not postal use to transport “real” letter correspondence. Likewise with the addition of the 3˘ Washington stamp.

However, this might be a very rare cover ( how many stamp collectors knew this AND took the time/travel/cost to do this) with both stamps bearing legit postmarks at this location: as the first day the Fair (FAIR Station, also) could cancel this stamp AND utilize the Inauguration of Washington 3˘ first day AND it is a R.P.O…

Camp Upton, Yaphank, NY Covers

Post card increased form 1˘ to 2˘ (right)

Camp Upton Headquarters -  General Bell censored post card 8/1918

LIRR Commemorative Covers

100th Anniversary cover of the Long Island Rail Road 1834-1934, RPO postmarked on the exact 100th anniversary date of the LIRR’s charter of 4/24/1834, on board westbound Montauk train #27 (Dave Keller archive)   Open letter postal card rate of 2˘ in effect (above) and 3˘ first class letter rate (below).

LIRR 100th Year Anniversary of  the LIRR 1834-1934 
Jamaica, NY  9/371934

LIRR 100th Anniversary service to Port Washington with insert 6/27/1998
Collection" Dave Morrison

LIRR 100th Anniversary Rough Riders Montauk encampment Camp Wyckoff  9/19/1998

LIRR First train 01/13/1873 125 years service
 to Port Jefferson. Cover 01/13/1998

LIRR RMLI 'Riverhead Railroad Festival' - RPO #4209 Riverhead  8/28/1999

Oyster Bay Station placed on National Register of Historic Places, 7/06/2005

Last LIRR RPO leaving Greenport via Main line 10th Anniversary 6/18/1975 
Collection: Dave Morrison

75th Anniversary Penn Station, NY City 9/20/1985

This philatelic cover commemorates the 75th Anniversary of Penn Station, New York, first opened November 27, 1910. The original station was demolished October 28, 1963. The new and current Penn Station is completely underground, and sits below Madison Square Garden, 33rd Street, and Two Penn Plaza. It is owned by Amtrak and is the main New York City station for the Long Island Railroad (LIRR), New Jersey Transit, and, of course, Amtrak. It also has MTA stations for both the 7th Ave Subway (1, 2, and 3 trains) and the 8th Ave Subway (A, C, and E trains).

This #6 unaddressed cover has a silk cachet by Colorano honoring both Penn Station and the ASDA 1985 Stamp Festival held above the station in Madison Square Garden. It has five U.S. stamps with a railway motif totaling the 22˘ postage rate in 1985. The pictorial cancel of Sep 20, 1985 notes the anniversary of Penn Station and the ASDA Stamp Festival. The back of the envelope has a red rubber stamp for Stamp Festival '85 and a blue rubber stamp for the U.N. Postal Administration.

100th Anniversary PRR Station, NY City 10/27/2010 
Collection: Dave Morrison

Stamp/postmark 100th Anniversary PRR Station, NY City 10/27/2010 
Collection: Dave Morrison

100th Anniversary First Train leaving PRR Station NY City 10/27/2010 
Collection: Dave Morrison

Port Washington Station Centennial Cover 6/27/1998

LIRR 130th year Anniversary trains to Greenport 
Greenport, NY 7/27/1974 Archive: Brad Phillips

LIRR 150th Anniversary of Steam 9/16/1984 Deer Park, NY

LIRR Riverhead Railroad Festival salutes RR Engineers 
Riverhead, NY 8/26/2000

LIRR 50th Anniversary End of Steam
Hicksville, NY  10/082005

John Bull Replica Dedication 
Hicksville, NY  5/07/2008

LIRR 175th Anniversary - Ariel 4/24/2009

The five- and ten-cent stamps of 1847 were the first adhesive postage stamps authorized for issue by the U.S. Post Office Department, in response to a law passed on March 3, 1847. 

The requirement to prepay the postage was not part of this new law, and many letters were sent as they always had been, without stamps, as in the example below on April 21, 1850. 

It was expected that the person who received the letter would pay the fee. It must be pointed out that a great many of the letters of the day were sent stampless, that is without pre-payment until the 1855 requirement that all letters be prepaid. 
Excerpt: "The First Regularly Issued Postage Stamps of the United States"  article by Bob Allen

     
Brooklyn, NY to Providence, RI via Greenport to Stonington, CT steamer
Cotton business stampless cover 5/02/1846

Cover cancel 1846 Sag Harbor to Brooklyn, NY
Note: First US postage stamp issue 7/04/1847

 
 Sag Harbor 8/06/1846 stampless letter - Towle 112-A-1 Archive: Matthew Liebson

Exterior of letter folded over into an envelope
Letter inside (left)


Larger view of the postmark with the handwritten date. July 26, 1850

LIRR stampless cover with brown ink circular hand stamp L. I. RAIL ROAD postmarked 7/26/1850. 

LIRR RPO Cancellations

Greenport to New York  - RPO 11/03/1894  Train #22

Greenport RPO to Patchogue US Scott UX18 postal card  3/15/1905
1902-18 ISSUES UX18 1˘ William McKinley, Oval

Oyster Bay to LI City  RPO postal card  10/25/1912

Oyster Bay to LI City Train #533 RPO 09/01/1909 Archive: Steven M. Swirsky

Montauk to NY RPO Scott UX24 1˘ McKinley Postal Card 3/14/1914

Greenport to NY RPO Scott UX27 Postal Card 9/01/1915

NY World's Fair First Day cancellation RPO "RAILWAY MAIL SERVICE" cancellation 04/30/1939

Oyster Bay to NY  RPO Scott UX27 1˘ Postal Card 12/17/1940

Port Jefferson to NY RPO Train #1649 
Scott UY7 1˘ postal reply card  11/27/1947 

RPO Exhibit Car last day 10/27/1940 NY World's Fair Collection: Dave Keller

RPO Cancellation NY Worlds Fair 10-12-1939
Collection: Dave Keller

Montauk to NY RPO 09/27/1940

Montauk to Greenport RPO 4/25/1952 Archive: Art Huneke

Train 623 was the westbound to NY handed back to him, returning on a later afternoon train eastbound Train 648 and then delivered through the postal system to his address in PA. Note: You can see the font for the train numbers differ between the two cancellations AND Train 648 is upside down! As for direction: rule of thumb has ALWAYS been evens/eastbound, odds/westbound. Research: Dave Keller 

Note: Jan 1st, 1952 post card rate (unsealed 1st Class) was 2˘.  Research: Steve Lynch

Montauk & NY RPO Train #32 6/30/1964
Collection: Dave Keller

Port Jefferson & NY Train #610  RPO 7/01/1964
Collection: Dave Keller

Port Jefferson & NY Train #645  RPO 7/01/1964
Collection: Dave Keller

Greenport & NY Train #211 RPO 6/18/1965
Collection: Dave Keller

Last day of RPO Service

Last day of RPO Service: Montauk & NY RPO cancel - Train #32  6/18/1965

Trolley RPO Service

BROOKLYN N.Y. CIRCUIT R.P.O.  TR.8 4/23/1906 cancelation. Brooklyn Rapid Transit (BRT) surface line mail streetcar. Note that, unlike RPO cancels on board a train, the "TR 8" indicated does not mean "Train 8" but "Trip 8."

According to "Street Car R.P.O. Service in Brooklyn and New York City" by John M. Price, M.D. (Mobile Post Office Society, Feb.,1979) the "TR" indicates trip numbers, and there were a bunch of them as well as a large variety of cancellations used in Brooklyn mail service.

One route began service in 1895 with the majority of others starting in 1896-1898. Most were gone by 1906 with a few venturing into 1907 and 1908. One route (Brooklyn & Fort Hamilton RPO) was a late starter and a late ender, carrying mail from 1906 until 1914 . Nothing after that. Archive/Research: Dave Keller
 

Brooklyn City Railroad (Brooklyn Rapid Transit) combination streetcar/RPO
(Railway Post Office) car #5. J. G. Brill Builder's Photo - 1895 (Dave Keller archive)

The Brooklyn City Railroad (BCRR) was the oldest and one of the largest operators of streetcars (horse cars and later trolleys) in the City of Brooklyn, New York, continuing in that role when Brooklyn became a borough of New York City in 1898. Incorporated on December 17, 1853 with capital of $2,500,000, a large sum in those days. Its first line, the Myrtle Avenue Line, was the first horse car line in Brooklyn, and opened on July 3, 1854. The line operated from Fulton Ferry via Fulton Street and Myrtle Avenue to the former stagecoach stables at Marcy Avenue.

The BCRR became part of the Brooklyn Rapid Transit (BRT) system in 1895.  Per roster data, this car was built by Brill in 1895 and it appears the builder's photo was taken prior to acquisition by the BRT as the car has been stenciled for the BCRR.  Info: Dave Keller