HDG TRACK DEV IN A NIGHT OP IN PROX OF ATA; CLASS D AIRSPACE WAS CONCERN #1. CONCERN #2 WAS THE LOW ALT CIVIL OP UNDER VFR FLT PLAN RULES BY SCHEDULED ACR DISPATCHED UNDER PART 135.

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ON 4/XX/94; I WAS FO FOR FLT OPERATED BY XYZ AIRLINES. THE FLT LEFT EWR AT XA35 EDT. THE CAPT CHOSE TO CANCEL OUR IFR FLT PLAN TO SWF AND FLY THE GOVERNOR'S ISLAND VFR DEP OVER THE STATUE OF LIBERTY AND THE TWIN TWRS OF NY CITY. AFTER LEAVING LAGUARDIA'S RADAR COVERAGE; THE CAPT INSTRUCTED ME TO NOT ACCEPT NY APCH RADAR COVERAGE FOR FLT FOLLOWING AND INSTEAD GO DIRECTLY TO SWF TWR. WE HAD COME UP THE HUDSON AT 2500 FT MSL AND BELOW AND WE WERE ABOUT 2000 FT MSL AS WE APCHED SWF. THE CAPT SAW A BEACON AND TERMINAL LIGHTS AND TOLD ME TO CALL THE ARPT IN SIGHT. I DID SO WITH SWF TWR AND WAS TOLD TO ENTER A L BASE TO RWY 27. AS IT TURNED OUT; THE BEACON THE CAPT SAW WAS ORANGE COUNTY ARPT; JUST W OF SWF. SO; OUR INADVERTENT L BASE TO ORANGE COUNTY TOOK US DIRECTLY AT SWF TWR. SWF ASKED US TO FLASH OUR LIGHTS AND WE DID AND WE WERE INSTRUCTED TO TURN R 090 DEGS FOR A L DOWNWIND TO 27. WE LANDED WITHOUT FURTHER INCIDENT. WE WERE TOLD TO CONTACT THE TWR WHICH THE CAPT DID AND I WAS NOT PRIVY TO ANY OF THAT CONVERSATION. HE TOLD ME THAT SWF SAID 'NO BIG DEAL;' BUT TO PLEASE ENTER THE PATTERN CORRECTLY NEXT TIME. WE SPOKE TO THE TWR IN PLENTY OF TIME; SO WERE ONLY GUILTY OF ENTERING THE PATTERN POORLY. IN MY OPINION; THE PROBS BEGAN WHEN THE CAPT CHOSE TO CANCEL THE IFR AND GO VFR. WE HAD A VFR TERMINAL MAP OF NY; BUT IT DID NOT INCLUDE SWF. WHEN I EXPRESSED CONCERN; THE CAPT INDICATED THAT HE HAD DONE THIS AND WAS FAMILIAR WITH THE ROUTING. SINCE HINDSIGHT IS 20/20; I LEARNED THAT I WILL NEVER AGAIN ACCEPT THIS ROUTING. NAVING THROUGH NY CLASS B AIRSPACE IS BAD ENOUGH WITHOUT BEING LOW; VFR ON AN UNFAMILIAR RTE AT NIGHT. WHEN I HAD FIRST BEGUN WITH ACR I HAD BEEN WARNED OF THE DIFFICULTY LOCATING SWF ARPT. SEVERAL ACR PLTS AND THOSE OF OTHER AIRLINES HAVE MISTAKEN ORANGE COUNTY FOR SWF. THE NDB IS 5 MI OUT NEAR ORANGE COUNTY AND THE NEAREST VOR IS 15 MI AWAY. IT IS RIDICULOUS THAT AN INTL ARPT WITH AN ALMOST 12000 FT RWY HAS NO VOR. UNTIL SWF GETS A VOR (OR RADAR); THIS WILL DEFINITELY CONTINUE TO HAPPEN.