Constable was the first Law Enforcement designation in the Town of Orangetown.  Believed to be during the  twenties and early thirties.  Constables were hired by local business until 1935 when the Orangetown Police Department was established.   In the following years the rank was re designated as Patrolman.  All of the Shields after "CONSTABLE" would have the word "POLICE".

With the influx of female officers the title designation of "Police Patrolman" was more appropriately changed to "Police Officer".  Orangetown shields always bore the title POLICE" or "ORANGETOWN POLICE".
Typical Orangetown Police Officer's Shield.
number designation continued with promotion to Sergeant and eventually to Detective Sergeant.
Upon my retirement in 1998, after almost 34 years of service, Chief Nulty authorized that my shield number 32 be assigned to my son who is a police officer with the Town of Orangetown. Although he knew of my request, he did not know that he was to receive the shield I wore before being promoted to Sergeant.

Shield to left is one of the original Sergeant's Shields.  Sergeant's shields through the nineties on the right had the number stamped on the back.  The latest Sergeant's shield, far right, incorporates the shield number continued from the police officer's badge.

Original Detective's shield  was replaced by the shield on the far right.

  The original design followed the pattern of designating a position on the badge during the earlier years without a number.

Eventually the shield was redesigned to be more consistent with the detective position while looking more official than the original.  The number on the shield is continued from the  police officer's shield carried as a police officer before promotion to Detective.
Detective Sergeant Shield similar to Detectives Shield.  Previously the Detective Sergeant carried the regular Sergeant's shield with "DETECTIVE" in place of "SERGEANT" and "SGT." in place of "N.Y."

Most recent shields, similar to police officer's, have a plate in the number area with the word "AUXILIARY" and "SPECIAL" with an embossed number below it. 

"SCHOOL CROSSING GUARDS" no longer have shields they utilize a reflective vest and a stop sign

Special shields, in the past, had been issued to Guards at  Lederle Laboratories since they would direct traffic in an out of the facility.  Eventually operating the traffic signals. 
With the advent of sophisticated signal controllers, manual operation ceased along with the Special Police designation..
During the late 60's the position of Chief and Assistant Chief Dog Warden was established.
Two Police Officers worked in this position during their off-duty hours.
These titles evolved to Dog Control then to the more appropriate Animal Control Officers.
"YOUTH OFFICER"is no longer used as a shield designation.
"DETECTIVE" has been the designation for a number of years.
The "YOUTH OFFICER SGT 202"  shield to the left appears with a number designation that was added by the officer
Small shield affixed to K9's collar.. Shield number designation was assigned according to date the K9 became a member of the department.

More info to be added
Recent discoveries by B. Lyons.adds to the mystery of old historic shields of the Orangetown Police Department. 103113