For regional airports I always liked (and still do) State College, PA (SCE) also called university park/happy valley/penn state. 5000ft uncontrolled strip that sits in happy valley in the middle of PA. Very green in the late spring early summer. Allegheny has a very senior crew base there, I was based there for a month when first hired but decided not to live there as it would have been years before I could have held capt there. Mesaba and ACA go in there too. Always a 20 knot TW on the ryw24 ils in the winter funfunfun. On final for 24 just to the north of the cl is bellefont a 3000ft uncontrolled strip. This area was one of the stops on the orginal mail run and there is one of thoes airway light beacons around there somewhere. Also supposed to to be a pitcarin mailwing in one of the hills around bellfonte.
Upstate NY airports are fun due to the ever changing wx. Mid to late May the area turns this awsome deep but at the same time brite green not seen anywhere else in the country except the NY, PA WV allegheny mountain region. Read "Fate is the Hunter" the first few chapters he talks about AM-21. This is basically all the airports in upstate we fly too. If you know where the orginal SYR airport was (pre WW2, down in Amboy) read where he talks about the "instrument" approach they used ref. the RR, canal and mountain south on the city. I can look out my apartment (or from the roof that is) and see what he was talking about.
Second would be Norfolk - many ships to see - if your goin into Chambers (Navy) landing 02 if I remember correctly you go right over carriers in dock, preety coll when your doin the PAR and pop out with the stern of a carrier in front of you.
As for major airports - you can't beet LGA or DCA. DCA especially now, we've got missles pointed at us, don't F*ck up over KRANT. Personally I enjoy racing blackhawks and other helos up the Potomac. Landing 15 is a blast, you come w/in 50 ft of the pentagon roof. can't believe they still let us do that. Plus don't land long or you goin for a swim.
If you look a the area ALG flys it encompasses the history of early America (rev+civil war) including alot of industrial history if you know what your looking for. Coal mining, steel mills, the whole Erie Canal system, Aberdeen by BWI, Hudson river valley, mohawk river valley, industrial revolution areas outside of boston.
When flying into LGA and they use rt traffic for 31 or LOC 31 you can pick out (if you know where to look) the remnents of Mitchelle field and its sister field the area Lindy used to takeoff for Paris. Also the old Gurmman (orginal plant not cav) and Bethpage aircraft plants.
And then there's Woodstock. If you go to Hugenot VOR
(HUO /116.1) north of Sparta VOR (SAX/115.7). Off of hugenutts vor to the NW is RAGER intersection. Just to the NE of Rager about 8 miles or so at a lake called Fillipo (sp?) is the field where woodstock 1969 took place. For some reason I always want to smoke a fatty when flyin up that way. Its about 8 miles or so west of sullivan county airport, that 5000ft strip in the middle of nowhere.