I think it was about five years ago, I was looking at real estate up in Washington County. I had a hot lead on a waterfront cottage for sale so I grabbed my son and we headed up for a weekend in coastal Maine. (We did spend most of day one sitting on a bench in Bar Harbor waiting to see what mega-celebrity was going to board a ginormous yacht, but I digress). After staying at my favorite little down east motel, The Blueberry Patch, we headed out to Eastport for breakfast (delicious Moose Island Bakery) – my first time in America’s easternmost city. As we parked the car by the waterfront, we saw a group of pirates headed towards us. Yes, pirates. As we walked towards the pier, we saw more pirates. Pirates were coming at us from all directions – big pirates, little pirates, baby pirates, even a few dog pirates. Unbeknownst to us, we had stumbled upon Eastport’s annual pirate festival, held every year towards the end of summer. The festival is traditionally held the weekend after Labor Day.
Tiny Eastport already hosts the largest fourth of July celebration in the state of Maine, and then swells to over 15,000 again a few months later to celebrate those plundering villains known as pirates (I do need to interject here that when I accidentally stumbled upon the pirate festival, it may have been a fluke, it may have still been early in the day, but I had no problem finding a parking space, despite the huge turnout). There are three full days of parades, fireworks, music, food, and fun contests for pirates of all ages. Visitors can participate in a bed race (yes, you read correctly – a bed race) or maybe bring your costumed pooch to compete in a pet pirate pageant. For the elder pirates, there is, of course, a rum party (and the following morning, a “hung over pirate morning rescue”). There is even a good natured plundering and pillaging of the nearby town of Lubec (But, never fear, Lubec gets their own chance to invade Eastport on a different day). It really is an experience in small-town festivities – which can be hard to come by these days, since everything seems so commercialized. So, just between us… let’s keep it our secret. And if you happen to be in Eastport in early September, don’t be surprised if you encounter some swashbuckling buccaneers wandering the streets and waterways – just utter an ‘ahoy, matey’ and join in the party.

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