Things to do

One of the best ways to enjoy yourself in the Hamptons and Fire Island is to go on bike rides once you arrive. There are many beautiful places to go, biking is low impact and a great way to exercise. I usually take my bike on the Hampton Jitney at the beginning of the Summer and leave it there untill I close the house. If you have an old rickety bike, then even better, because you don’t have to worry about it. I find that the side roads are the best and you can usually do 2 to 5 miles without much effort. When I first started riding I didn’t have a map, I just pointed my bike and rode (make sure you wear your helmet, I don’t cause I’m nuts).

One of the nicest rides is to the beach especially if your house is a ten minute walk or more. You can lock your bike up with a cheap lock, I usually don’t because I feel that people respect your stuff but the real reason is that my bike is old and dangerous looking. There are also places to go off-roading if you have a mountain bike. Some of the best places are off Route 27 on the way to Montauk to the left. Take any of the breaks in the road and head towards the train tracks. This time you must wear you helmet. I also find the ride to Montauk from Amagansett quite exhilarating, its long and very windy going toward Montauk and there is a big hill half way there. If you’re really in shape, take Old Montauk Highway that breaks to the right when you get past Cryril’s, the hip seafood restaurant on the left. Old Montauk Highway will really test your endurance. I think its well worth it (so I’ve heard), the beautiful ocean views are spectacular to the right. I usually take that route when I drive, it’s like a roller coaster ride and I usually go way too fast, just for the thrill.

Another nice bike route I like is on Further Lane, which is between Amagansett and East Hampton on the ocean side of the train tracks. On Further Lane you ride by some beautiful estates, an enormous golf course and is a fairly easy and flat ride.

If you are vacationing on Fire Island everybody has a bike. Biking is the best and nearly only mode of transportation since cars aren’t allowed. The streets there are narrow, well not that narrow, and very easy to ride. Fire Island is fun to explore by bike. You can ride from party to party at night. Make sure that you don’t get too drunk because you can get ticketed if you get caught.

You can also purchase maps but I think exploring is the best and most fun way to bike. Nothing feels better than taking a ride in the afternoon when its not too hot and then coming back to your house and having some cocktails before you go out. I will keep you updated on new trails that I explore.

Getting there

Getting to the Hamptons can be an interesting and harrowing experience depending on what mode of transportation you decide to use. Before I had a car I preferred using the Long Island Railroad, it departs in Manhattan from Penn Station at 34th street. You can either enter on 7th Avenue between 33rd and 34th street or there is a new side entrance on 34th between 7th and Eighth. If you are leaving after work on Friday, be prepared to fight through the crowds, it can be very hectic. The earlier in the day that you leave, the better. You have to go down a few levels, where you will see a mass of people; commuters and people like you.

There are several ways to purchase your ticket. You can wait on the huge ticket lines that seem to move pretty fast or you can use the vending machines. And if you’re running late or are uncoordinated, then you can purchase your tickets on the train (there’s usually a service charge for that). Once you buy your ticket you have to be aware of the track numbers that are posted overhead so don’t wander off too far because once the track number is announced you have to compete with hundreds of other commuters to push your way towards the entrance to the track, kind of like a gladiator. So the more aware you are, the better off you will be.

Try not to bring to much carry-on because the over-head racks on the train you connect to don’t hold a lot, they’re very shallow. If you want to bring a bike, you can’t take it during peak hours and you need a permit that you have to apply for.

Once you finally get aboard (I know this all sounds like hell but it can be pretty fun and it’s well worth the payoff) and if you don’t get a seat, don’t worry because you usually have to make a connection in Jamaica Queens. After you do this a while you will be able to figure out where to stand so that you’re at the perfect spot for your connecting train. Remember to always hold on to your ticket, especially when transferring.

The train that you connect to is very nice, they’re double-deckers and everybody wants the top part for the view, but I usually take the bottom because it’s easier to get a seat. The ride once you’re aboard is very enjoyable unless you have to stand but you usually get a seat. There is a bar car that serves beer and snacks and water. Remember to tip the bartender. The bar car is actually a good place to hook up with fellow Hamptonites and Fire Islanders and exchange numbers. A special note: make sure you don’t miss your stop, last summer I didn’t get off at Amagansett and had to take a taxi back from Montauk. What a pain - it cost 30 bucks.

My advice to you if you’ve never taken the train, check it out - it can be quite the social scene.