Strolling Southhampton, Guzzling Around Greenport, Meandering Montauk

I grew up in Freeport, NY, a town on the southern shore of Long Island. One of my best memories was the summer between 9th and 10th grade when two friends and I decided to bicycle from Freeport to Montauk at the eastern end of Long Island, roughly 100 miles away. No one called it a century ride back then but I guess that is what it was.

The plan was to bike there, meet our friend Wes who was camping with his family at the Hither Hills campground, stay the night and then bike back. Its amazing our parents let three dopey 15 year-olds do this but it was a different time back in the day. Its also amazing we actually made it as back then there was no such thing as a water bottle on a bike and the start of the art for bikes (at least what we could afford) was a 5 speed Schwinn.

I've never been back to the east end of Long Island, so when Carole and were planning a get away weekend for our anniversary, I decided we'd spend the weekend there. I booked us a room at the Butler's Manor bed and breakfast in Southampton. It turned out to be a fantastic place, run by a very friendly couple. We arrived about 7pm Friday night and at their suggestion we walked into downtown Southampton and had a great meal at 75 Main (though the crab cake was not up to true Maryland standards) on Halloween night No Paris Hilton sightings, but plenty of rich people in country club regalia at the bar.

Saturday morning we headed towards the North Fork of Long Island via the Sag Harbor and Shelter Island ferries. Sag Harbor was a cool little town but we spent the most time in Greenport which is an arty little place. Carole made me do tea with her in a hoity toity tea parlor, where I held out my little pinkie as I ate my brie and pears. We then headed west towards Cutchouge and stopped at three different wineries - there are dozens of them out there. Renting a limousine to drive you around to wineries on a Saturday seems to be a popular Long Island past-time - the parking lots were clogged with obscenely long white limos. One detail that is probably unique to Long Island wineries: they all charge for tastings to keep the millions of college kids from using tastings as a free way to get a buzz.

Sunday morning was time change day, and since breakfast at the Inn wasn't until 0900, and we tend to wake up early. we were out the door at 0600 to hit the retro-looking Southampton Starbucks (soon to close) and then take a hike along the Southampton beach area. We did about a four mile look, walking along the shore behind the multi-million dollar mansions and then returning on Gin Road in front of the MMDMs - though from the road all you see are 15 foot tall hedges everywhere. Then back to the Inn for a phenomenal breakfast and we were off to Montauk.

Montauk is a refreshing change after all the chi-chi-ness of the Hamptons - really mostly a fishing and camping town with a cool lighthouse. We tromped up the 148 stairs to the top and had an amazing view. When you look around it is hard to believe you are in New York - in fact, most of the east end of Long Island (especially the North Fork) looks more like New England than New York or Long Island. The beaches were full of surf casters - I have never once in my life ever seen a surf caster actually catch a fish, but I guess they are a hopeful species. We did some shore walking, took at look at the fishing boat area and then started to make our back towards the Islip airport. We made a brief stop to see Lake Ronkonkmoma, which I remember as a huge lake we occasionally stayed at when I was a kid, but turns out to be more like a large pond.

We didn't do any biking or kayaking but a very cool place to do both of those on a future visit. I'll close with the view from the top of the Montauk lighthouse:

Comments

[backpacks luggage]

Interesting and in fact a nostalgia evoking story. Why is it that nowadays a parent wouldn’t dream of letting their 15 year old cycle for a hundred miles? Is it because the media inform us of every miscreant making us believe that there are so many out there or indeed are there more nasty people in the world than ever before?