Natalie Portman Envy in Syosset
Overview: I come from a town on Long Island's north shore called Syosset. Known for Jewish American princesses, Natalie Portman envy and it's not so secret gambling and coke addictions, Syosset is not only a great place to visit, it's also a great place to live. When the kids in my high school class used to complain about having to buy a book, the teachers would always give us a, "what does it matter to you" look. The usual cheeky response was "There IS a trailer park in Syosset." With trailers running you a quarter of a million, the residents aren't exactly complaining about laying out the 5 bucks for a copy of Macbeth, they're more likely to complain about reading it.
Where the cool kids are: Like most towns on LI, when the temperature rises the slightest bit everyone rushes to the local ices stand. In Syosset, it's Ralph's Italian Ices on Jericho tnpk (in fact, there may just be a law that there be a Ralph's every 20 square miles on LI). I used to come here as a punk kid senior year. I'd drive up in my parent's Volvo station wagon, stand on the enormous line, order a pina colada ice, open the trunk of the car and sit inside with my friends listening to Billy Joel. We were so cool. No wonder I gained ten pounds that summer and didn't have a boyfriend.
Booze: I'm a dive bar, cheap date, kind of gal myself, but even I wouldn't walk into Syosset's only Irish pub, Mitch O'Neil's. The beers may be cheap but the atmosphere is distinctly Twin Peaks. Though Syosset boasts the lowest crime rates on all of Long Island, you have got to wonder what these cyclops bar bumpkins are up to at night. My guess? They head to the next town over, Hicksville (no joke) and harass junior highers at the mall. One meander in here when I turned 21 was enough to put me off venturing south of the train tracks again. My presence was met with a stony silence and bleary leering- the kind of atmosphere that makes the jukebox come to a screeching halt.
If you are looking for some decent bars, filled with men with money in their pocket, I'd head north 15 minutes to Huntington Village. Often called the NYC of LI, Huntington has a nice casual feel and after you stumble out of one of the dozen cozy pubs, you can grab a slice at either Rosa's or Village Pizza, both of which vie for the best pizza on Long Island.
To drink for free during the middle of the day, you can't beat a tour of Long Island's wineries situated up and down the north and south forks of The Island. The local wineries provide tastings all day and, if you are looking to pick up a bottle, have the best prices right from the source.
What else to do Friday and Saturday Night: Go to the city. And if you can't do that, there is always a ton of trouble you can get into on The Island. During the spring and summer, I like to put on my best Long Island, gumba accent and head to Robert Moses beach on the South Shore. Armed with a cooler full of beer, grab one of the fishing boats docked at the marina and head out to sea. It doesn't matter which boat you choose, though I'd probably go for the one manned by the sexiest Southie. The deck hand will provide you with all of the fishing gear and will even clean your fish. If you don't get seasick, it's a great way to spend an evening listening to classic rock, and getting trashed with your friends while still being able say you went out on Friday night.
Music: It is a requirement that before any high schooler bound for college is allowed to leave The Island, they must first memorize all the lyrics to every Billy Joel song, or at least 'We Didn't Start the Fire.' If that song ever plays on a jukebox anywhere in the world and some schmo is drunkenly singing every word, there is a 99.99% chance he is from Long Island.
Venues: For your big music festival type deal, the Nassau Coliseum during the summer is your place. But if standing around with a bunch of middle school kids and their parents isn't your thing, I'd check out the summer schedule at Jones Beach. Without a doubt, it is the most beautiful spot to see a concert in all of New York. Situated facing the beach, most locals know enough to bring beers and drink them on the water before heading into the show. Miraculously, I saw two Lilith Fair concerts there when I was 16 and 17 and still didn't end up a lesbian.
Long Island is the birth place of some of America's greatest comedians, Jerry Seinfeld, Eddie Murphy, The Baldwin brothers, so it is no surprise that all across The Island there are great comedy clubs where Long Islanders can combine their two greatest passions, laughing at other people and booze. Two of the best and most famous clubs are the Brokerage in Bellmore and Governor's in Levittown. While both are relaxed and fun places to spend a night out, Governor's usually has the more famous comedians stopping by and serves a good and inexpensive food menu.
The Beach: It may sound cliché to those in the know, but the best beach bang for your buck is still good old Jones. While some beaches on the north shore in the summer run you about $15, Jones is only $8 and comes armed with every freak Long Island can muster, making it the perfect place for people watching. Not only that, the lifeguards at Jones are straight out of the pages of an Abercrombie catalog, the waves are big and the sands are clean. Just watch out for the notoriously brave seagulls.
Long Island Creeps Me Out: Why Long Island would need twelve massive insane asylums, Syosset even has a sanitarium, I will never know. Most of these huge complexes are abandoned now, but tales of the cruelty that went on there pervade the LI psyche and can make any "Strong Islander" buckle at the knees. It is common practice that every Long Islander make a pilgrimage to at least one of these sites in their lifetime at night, attempt to break in, hear footsteps/a door creaking open/manic laughter and run away screaming with their friends. Hey, it beats the planetarium. My asylum of choice? The one in Amityville. Drew Barrymore's great-grandfather died there and after you run away panicked, you can always hit up the Amityville Horror house down the road. I hear it's for sale...again.
If the asylums don't scare the crap out of you, may I suggest Mount Misery. There are lots of frightening tales about Mount Misery, including my sister walking though the woods there and coming across an old cabin with a man holding a chainsaw outside and my uncle as a kid sitting in a dark car with his friends at the top of the road daring each other to get out when a ghostly blue light lit up a grave in the distance and their car suddenly stopped running. Mount Misery is the kind of place movies with big breasted girls running and screaming are made of. Tales include a woman in white walking along the road who jumps in front of cars and the story of a young girl molested at a horseback riding camp in the woods. The girl's father apparently didn't believe her so she killed him and the rest of the counselors. But I used to go to that camp and I am pretty sure my instructors weren't ghosts. Or at least they were ghosts who knew how to deposit a check.
Where to Stay: If you are heading out to Long Island during the summer, there is a fair chance that you are one of the thousands of Manhattanites making the weekendly pilgrimage to The Hamptons. If you are desperate to get in on some of the celebrity stalking, random sex and Porsche envy that happens in The Hamptons, then I suggest finding someone with a house-share you can get in on. If you don't know someone personally, NewYork.Craigslist.org should be able to help you with that.
What I suggest, however, is going a bit off season and renting a condo in Montauk, or "The End", as locals like to call the town because it marks the furthermost spot on LI. Montauk is about 20 minutes down the road from the Hamptons along a beautiful two lane stretch of highway, surrounded by water and wildlife on both sides. Most condos in Montauk can easily fit 6-10 people, making the price about a hundred a person for a long weekend. Most of the condo complexes are right on the beach, have pools and are far enough away from the sickly snooty Hamptons that you'll actually be able to enjoy yourself without worrying if your shoes "are SO last season." The Long Island Railroad has a stop in Montauk and takes about 3 hours to get to from NYC. The Surf Club Condos are a particular favorite because of the close location to the main drag of Montauk. Main Street Montauk consists of the BEST pancake place on Long Island,- Mr John's, a bait shop and a corner store selling that most important of condo necessities, beer.
What Else to Do While in "The End": Shop. If you are thrifty bastard, like myself, you love a good bargain. Before heading back west, I usually stop in at the Riverhead Outlets. The Outlets mark the end of the Long Island Expressway and the beginning of the Montauk Highway and contain such child sweat-shops as The Gap, Maidenform and Puma. It is a good half way point no matter what direction you are traveling in.
Getting There and Away: The Long Island Railroad is your best bet onto Long Island from pretty much anywhere. There are more creative solutions, like taking the ferries from Port Jefferson on the North Fork to Connecticut or the Hampton Jitney from midtown Manhattan to locations throughout the Hamptons, but you can't beat the new, clean trains from Penn Station for about $14 round trip. The trains used to be so rank that sitting near the bathroom meant that you would smell like shit for the remainder of the day (my sister couldn't wash the scent off once for two days, we had to hold our noses around her). The brand spanking new trains, however, are shiny and white and as cold as an ice box in the summer. Not to mention, the bathrooms are now so big that not only is sex a comfortable and cleanly experience, group sex ain't bad either.
Once you get to the town of your choice, the only real way to get to where you are going from there is a taxi. There are public buses from some of the bigger stations (Hicksville, Huntington Station, Mineola and Rockville Center for example) but from most stops on the North shore, you'll have to bust out the extra cash for a cab. But don't despair, taxis on Long Island are pretty cheap and shouldn't run you more than a few bucks.
Websites:
Montauk Life
Long Island Tourism
Long Island Wineries