Mid atlantic list:
Tangier Island, VA - strange accents, only 5 family names, good eats and bed and breakfasts.
Luray, VA - go visit the caverns. Pretty cool to cruise at 7,00ft to get there and then spend the day 200ft below the earth. Cars available to drive you to caverns or golf course (free transportation).
Kentmoor, MD - 2000ft grass strip just south of the Bay Bridge. Owners have hangars instead of garages on this fly-in community. Park in the transient spots closer to the Bay and walk a block down the street for great crabcakes at the Marina Restaurant.
Clearview, MD - Nice little pilot shop and great gas prices always BUT you have to be able to land in 1500ft or you are going off a cliff. If you land there safely, buy a mug that proves you are a "better" pilot and that you know what airspeed means.
Richmond, VA - land at the "big" airport, park at the FBO and walk to the Air museum - nice Saturday diversion. Some neat displays in the museum and worth the fee. Seems like you paid too much when you walk in, but there are little interesting displays all over and something will catch your attention. I know - I thought I was ADD (attention disorder) but then found some neat things.
And then there's golf and I mean close to the runway - Bryce Mtn resort in Bayse, VA, Wisp at Garrett County, MD and Butter Valley up at Perkiomen, PA. For upscale, go to Nemacolen, PA near Pittsburgh. Nothing like landing, tieing down and playing golf in 20 minutes.