CloudDriver wrote:
My suggestion - Chestertown is on the east side of Chesapeake Bay. Head north on local roads to I95 to the NJ Turnpike. Near Woodbridge NJ, take I287 to the NY Thruway north to I84 to the Mass Turnpike, then I495 around Boston to join I95 into New Hampshire and Maine.
Zero low bridges or tunnels on this route.
I'll second this route.
I95 through NYC is a gamble with traffic. When there is no traffic, you speed up and your TT will bounce all over the place. Odd hours (night, etc) there is usually construction.
I don't like towing our 21ft TT through NYC, and avoid it if at all possible.
Having said that... I84 can be rough, as can be I495. Okay, all the highways in New England! lol. Massachusettes has come weird aversion to re-paving bridges - the highway will be beautifully paved right up to a bridge, then your TT will bounce over your truck going over the bridge.
Having said that that... Have fun! Let us know how the trip goes.