The summer is the summer and I would not advise making a special trip north unless you really want to travel north.... Our view is also to go north and so we get 5 or 6 boats to go north to Bristol RI in August This is the best chance for breeze... (and certain butt kicking)

Schedule is
April, West River
May, Gunpowder
May North Americans
June West River
June Rock Hall YC
July Cambridge YC
July Corsica River YC
August Bristol RI,
Sept West River YC
Sept West River YC
Sept 50th Aniversary of Roten Point YC
Sept Lake Hopactong YC
Oct West River YC
Oct American Yacht Club (Southern Connecticut 1 hour North NYC)

I think the Va Beach guys are the ones who can swing either way easily. They host a late May regatta but the NA's conflict this year (EMSA and Fleet 32 Sail the Bay regatta). I would coordinate with those guys about a travel regatta.

In general.... I think the schedule would be great if West River continued with their event on the last weekend of April and Va Beach had a regatta at the end of May... Bristol Ri in August and Hopactong and American YC in Sept and October.