The best time to go down to Cape Cod for a few days

may in the week before Memorial Day.
Granted the Cape is still fitfully stirring from it's annual Odinsleep, your favorite restaurants may be entirely seasonal and thus it's impossible to get a good meal after 9pm.
Moreover a fitful Nor'easter may be battering the peninsula as well, drizzle and wind at night and whole of Nantucket Sound churned up like Captain Ahab's worst nightmares during the day. The sun usually batters its way out by noon, but at four pm the mists come loping back across Provincetown Harbor with studied insolence.
But you shoot right over the Sagamore Bridge, there is little traffic on Route Six and no lines for anything at all. You can cruise the Cape Cod Rail Trail from Eastham to Wellfleet in a Charlton Hestonish Omega Man solitude.
You can explore the last of Primeval Cape Cod on the Fort Hill Trail with it's Red Maple Swamp, on a grey drizzly day you could actually believe just for a moment that these were the wild moors around Culloden and Bonny Prince Charlie's Highlanders are about to make their last stand for Scottish Liberty.
Of course you never quite escape the sound traffic on Route Six, but if you close your eyes and imagine real hard....
I saw a surfer on Nantucket Sound at the Cape Cod National Sea Shore braving the obvious rip tides, as he sped along a seal black and curious surfaced to the height of the animals shoulders about a hundred feet away. The beast gave the surfer a disdainful looking over and seemed to think to itself "AMATEUR! Needs a board to float...."
By the way, seals have made a comeback on the outer Cape, How Cool Is THAT???
I walked from the Coast Guard Station to Nauset Light and thanked God that President Kennedy had the foresight to sign off on the Cape Cod National Sea Shore, otherwise it would all be the ruins of Howard Johnsons by now.
Provincetown has lost none of it's charm or it's Boho street cred. The streets were just filling up when I got there. Those dunes over Route Six loom over the Cape like the Alps.
I also bought a bottle of wine from a local vineyard in Truro of all places, will advise when the bottle is appropriately sampled.
For the record, the daily wine tasting therein was packed.
And I even got an opportunity to see "Pirates of the Caribbean IV, On Stranger Tides" and "Thor" at the Wellfleet Drive In. If all else had gone to smash, that alone would have made the trip worthwhile. For the record, the Wellfleet plays the National Anthem before each Double Feature, I heartily endorse this practice.