Millennial Musings: Off-Season Odyssey


When most people think of the Hamptons, they think of summer. My family are not most people. Our last family winter vacation was five years ago to Nassau in the Bahamas and we were plagued with bad weather, amongst other not so fun vacation things. While trying to convince my parents to go on a family getaway this year, promising it would be nothing like the Bahamas and hoping it would be something more like Italy, we settled on the Hamptons—a collection of towns in the South Fork of Long Island, New York, that includes Southampton, Bridgehampton, East Hampton, Amagansett, and more. At the very tip of the Atlantic coastline is Montauk. Sag Harbor and Shelter Island are further north, on Peconic Bay.

This was a far cry from Italy but also a place of significant meaning for us. It was my birthplace and where we spent the first few months of my life as well as where my parents spent a few years together before I was even an apple in their eye. So it was a history trip.

A note about visiting the Hamptons in the winter… yes you are right in assuming that many places are closed and there is not much to do past dinnertime. Wanting to stay somewhere nice, we got a suite at The Rams Head Inn on Shelter Island. Lucky for us, it was the only restaurant on Shelter Island that was open the Sunday night we arrived (and it was very good, I might add—great food and a cozy atmosphere). We happened to be the only guests staying there for the two nights that we had reserved and we were treated pretty royally.

The only problem with a Sunday night on Shelter Island in the middle of the winter is that there is absolutely nothing to do once the sun goes down except eat dinner at this one restaurant. We spaced our courses out as long as we could, but ended up in front of the TV watching 60 Minutes and the Homeland season finale with little choice but to go to bed by 10pm.

Winter Family photoAs far as memory lane trips go (keep in mind my memory holds nothing about the Hamptons, but my parents’ hold everything) we pretty successfully toured the east end of Long Island. We walked around downtown Sag Harbor during the day stopping in all the stores because there were year-end sales everywhere.

We drove all the way out to Montauk, my dad hoping for us to have lunch at a place he remembered from his childhood… only to forget that it’s winter and most of Montauk is closed. It was a pretty drive though! After stopping for lunch, we headed to East Hampton, which to me felt like a mall with all the chain stores and wealth—not the cute Long Island town I expected. We walked around for a little before going to see a movie to pass the time and trying once again to have a long dinner.Hamptons father and daughter

In the summer in cute little northeast towns it’s not unreasonable to expect ice cream or fudge or salt water taffy to be on the agenda. Yelp (an app I no longer trust) told me that there was a fudge place open until 11pm in South Hampton so considering it was the only Hampton we hadn’t been to yet, we decided to try it out. Well, Yelp was wrong. Like the rest of South Hampton except for a few restaurants, the fudge shop was closed, so we headed back to Shelter Island.

As we headed out of the east end of Long Island, we had to pass through Riverhead, my true birth place, to see the Big Duck (a little building/gift shop in the shape of a duck originally built in 1931), which to our disappointment, was also closed. The rain did not stop us from taking pictures though, to compare to the ones we had from when I was a child.

Despite the early nights and plentiful closings, the Hamptons are fun in the winter for one big reason: getting to spend a lot of quality time with your family and learning more about them than you ever knew.Hamptons Duck

For handy travel information, from transportation to hotels to nightlife, go to the Hamptons Travel Guide on Concierge.

About the restaurants. . . since our trip was off season, we spent a lot of time eating. A good lunch place in Sag Harbor with great coffee (especially if you’re tired from walking around and shopping) is The Golden Pear (with locations also in Southampton, East Hampton and Bridgehampton). We also stopped at the Sag Harbor Baking Company for some delicious muffins! When we found out everything by the Montauk wharf was closed, we were advised to go to Naturally Good Foods & Cafe downtown for the “best fish tacos”. Since I live in Los Angeles, I’ll admit I’m a snob when it comes to fish tacos, but these were pretty good! Our East Hampton dinner was at Rowdy Hall, known for their burgers (which were tasty and juicy).

I also must add that if you’re ever driving through Long Island, you absolutely most stop at A&S Fine Foods in Huntington for the most amazing Italian deli sandwiches and cannolis. I should also add that after a long weekend with your family stuck in traffic on your way home with lots of accidents due to rain, the last thing you should do is stop at Bloomingdales.

About Sara Dolin

Sara Dolin is an aspiring TV writer living the dream in sunny Los Angeles. Freelancing on a variety of reality and scripted shows (“The Neighbors”, “Necessary Roughness” and “Project Runway” to name a few), she is also a contributing writer on her mother Deborah Batterman's blog: All the small things: a mother-daughter diablog. In addition to always looking ahead for her next job, Sara is also always looking for her next adventure—from the South Pacific to Europe to the Middle East to a road trip across America, she’s gotten a taste of the world and like The Little Mermaid, just wants more.