A Masshole Visits America: Brooklyn, Jersey Shore

Earlier this year, I confessed to my business partner that I was burned out. Not in the way you are after finishing a really hard presentation or planning a major event, but the way you are when you find yourself staring out at the freighters along the Southie waterfront and thinking, “maybe I should join the Merchant Marine.” And instead of casting that crazy notion aside, you go home that night and Google to find out what that would entail. I was exhausted: In 2004, my business partner and I had started a software company, and a central part of the reason why we were still partners—and friends—was that we could be completely honest with each other. “You need to take a long vacation,” he told me, and considering my last one had been in 2005, he was right.

Photos by Colin Kingsbury

So on Friday afternoon last week, I locked up my apartment, handed the keys to an ex-girlfriend marooned out in commuter-rail country, and pointed my car south for a road trip that would last until September. Though I had enough frequent-flyer miles for a ticket to anywhere in one of those first-class compartments that come with unlimited free drinks and a confidential secretary, a trip like that would have required planning. I’d spent the past seven years growing my business from zero employees and only a few more customers to nine employees and almost 250 customers, and while I could have taken a week off here or there, I could never get around to planning for it. Hopping in your car and driving around the country with no reservations is to vacations what eloping in Vegas is to weddings. My only plan was to leave as early as I could in August, and head south toward New Orleans and on to the Pacific. Besides, I’d just bought the first car I’d owned in three years, and what better way to roam the country than in a convertible?

I pulled into Brooklyn at 10:30 that night after driving through downpours in Connecticut and Rhode Island. I’d decided to take the first couple days slow, and met up with an old friend at the Wythe Hotel in Williamsburg. We sat in a bar with a commanding view of the Manhattan skyline and the conversation turned to Bloomberg. I’m pretty sure that if the President was elected by residents of the five boroughs, the onetime Medford resident would be a shoo-in. Fortunately, the rest of the country gets more votes, because given the opportunity, Bloomberg would find a way to have himself declared emperor and force us to get up every morning at dawn for North Korean-style mass calisthenics. In the past 20 years, I’ve watched Times Square go from a place where you could buy coke on the street in midday to one where, soon, you won’t be allowed to buy a large Coke at any hour of the day. Bloomberg has the brain of a technocrat and he’s done great things to consolidate the remarkable transformation that began under Rudy Giuliani in the ’90s, but I’m convinced he also has the heart of a tyrant and is utterly sure that if the rest of us could only see things as clearly as he does, we’d submit joyfully to his sensible rule. I’m glad he left Massachusetts.

The next morning, I departed the land of no smoking/no soda/hold the salt/ride your bike and headed for Atlantic City, an easy two-hour drive that I extended to three by diverting through Asbury Park and along the shoreline to Seaside Heights for lunch. I’d love to dispel all the misconceptions about the Jersey shore, but journalistic ethics dictate that I publish this picture taken at the Sawmill Cafe on the boardwalk:

Snooki and her band aside, the Jersey shore has more than a few moments of charm and beauty to rival Cape Cod, and the ocean there has always felt more, well, oceany to me, with its six-foot breakers that throw you around like a toy poodle. It’s culturally a world apart from the popped-collar snobbery of the Cape and Islands, but if you can’t enjoy cheap beer and pizza right on the beach and losing 10 bucks trying to win your significant other a giant stuffed animal, then you probably ought to just move to France already. I polished off a Miller Lite and a $3 slice the size of a road map that would vie with the best I’d ever had in Boston, and headed toward Atlantic City to find a cheap room, a buffet dinner, and hopefully some good luck at the craps table.