Sixty-Something: My Favorite Hamptons Halloween Party

It’s amazing how folks are enjoying Halloween costume parties more and more as they get older. There was a period of time when my kids were very young that I would buy some sort of mask and walk them around the neighborhood with a flashlight. For us sixty-something folks, the idea of our parents walking us around for Halloween is laughable, but yes we helicoptered our young ones.

In my kids’ grammar school years we lived on the corner of Oak Lane and Clay Avenue, directly across from Prospect Hill School in Pelham Manor, New York. Our house was called the “Whale House,” because we had a whale weathervane atop of on the roof and a black whale painted in the arch of the home along Clay Avenue. It came that way when I bought it in 1990.

Being on a corner across from the school, we always had a minimum of 300 trick-or-treaters. That was a lot of candy to give out every year. It was cute, the very young often shy looking up at you through masks in costume.

In 2004-2005, when I was a divorced, single 51-year-old, I rented a room on Barnes Lane in a home in the center of East Hampton Village. It was right behind the Golden Pear and Sam’s Pizza, actually in the center of town. I was new to living full-time in the Hamptons. I sailed a lot and had four jobs to make ends meet. When summer ended most of my city friends went back up-island on “Tumbleweed Tuesday,” the Hamptons name given to the Tuesday after Labor Day. During the time I lived right in the Village I became somewhat neighborly/friendly with the shopkeepers, and townspeople. They’d nod at me and I at them, although we really didn’t know each other.

Other than visits from former friends from Manhattan I spent many weekends writing articles because it was about this time I started earning my keep by writing. My social life was quiet as I was healing from my divorce.

I remember being told by Ben Dollinger, the then Blue Parrot bartender, that I should go to the Halloween Party at Rowdy Hall in town because “it is a really good time,” but to go, I had to wear a costume. At the time I knew the folks at Rowdy Hall because I watched many baseball games there sitting at the bar alone, but with the others who were alone.

When Halloween rolled around I bought a cape, and a top hat and decided to walk the very short distance to Rowdy Hall. When I arrived, a manager there was collecting the entrance fee, but waved me in for free. The band that night I believe was “Little Head Thinks,” and they were playing their Stephen Talkhouse popular covers song list. I ordered a drink and took in the sights of some the best costumes I have ever seen anywhere. It was strange because at first I thought I didn’t know anyone, but eventually I realized I knew everyone. In Rowdy Hall that night were the folks who nodded at me daily. I danced with shopkeepers, waitresses, crossing guards to the songs of the band. We partied like in our college days. The beers and drinks were flowing and it was such an unexpected great time.

It was that night that I first realized what tight communities the East End villages are. Over the last 15 years I have had the privilege to report on many things of the East End. Town Board meetings about controversial topics, film festivals, shows, fundraisers for hardship cases, huge real estate deals, and local business stories. I did a weekly Top 50 Traditions of the Hamptons that was well read and did a few obituaries, too. I learned about the true civic souls the East End communities have.

But it was that first Halloween party at Rowdy Hall that made me feel at home in the Hamptons. It was the first time I felt the soul of the East End come to life.