The Off-Season Hamptons Getaway
What to do, where to eat & where to caffeinate
“You live in the city? Is it everything you ever dreamed of?” a new friend from Montréal asks as she pulls out her phone and shows me her screensaver: a painting of a woman reading and drinking coffee from a window seat that overlooks the bright New York City skyline at night. I often get asked questions similar to hers when I come across those who, like me, once had dreams of living in New York. While in some ways it is everything we want it to be, there’s definitely a limit to what can be romanticized. When that limit is closing in, I hop in the car (or on the train) and head out East. The relief that overcomes my body when I see the lights of the city fading into the distance behind me is a feeling I highly recommend for all city-dwellers at one point or another.
Everyone knows the Hamptons as the Summer playground for wealthy New Yorkers, but these quaint towns have a lot to offer amidst the typical off-season. Come the end of August, when the last sun-crisped city folk are bound for Manhattan once again, little towns all along the Hamptons sigh harmonious breaths of relief from the hectic Summer heat.
Slowly, Summer turns to Autumn and Autumn to Winter. As the seasons shift and the city settles, one might find themselves in need of a getaway. Thus, a quiet visit to Long Island’s sleepy beach towns might be just the cure for the urban-dweller’s winter fatigue.
Interested? Follow along with me on a day trip out East!
Leave the city around 8:30am
I have always done this trip by car so that we can stop at a bunch of little places along the way, but if the train is a more available option for you- last stop on the LIRR Montauk Branch is Montauk, and luckily it also hits some of the more popular Hamptons towns, such as Southampton, East Hampton and Amagansett. Any time by the ocean is healing time spent.
First stop: Amagansett
Jack’s Stir Brew Coffee in Amagansett has delicious coffee and other drinks, along with some of the best vegan pastries. The apple cider donuts and blueberry muffin come highly recommended. There’s even a picnic table around back for you to sit and enjoy your morning start.
After Jack’s, take a walk across the street to Innersleeve Records store for a peruse. If you’re more into home décor and fashion, the shops next door are equally as enticing (our favorites are Lazypoint, warm and Love Adorned).
If you want to get lost for a little while, take a turn down any of the neighborhood roads and enjoy the beautiful houses, vintage cars and luxurious scenery. The Hamptons towns and neighborhoods are home to some of the most expensive real estate in the world, and are even featured in reality TV shows: Million Dollar Beach House, Summer House, etc.
There are comfort stations in the bigger towns for restroom purposes, so head back to Amagansett’s main strip before continuing on.
Second stop: Montauk
With bellies full and energy high, drive down to what Long Islanders fondly refer to as ‘the End’, i.e. Montauk! This drive is a beautiful one down to the end of NY State Route 27 aka Montauk Highway; few will forget the first time they see the Atlantic ocean from around a bend in the road, hidden by trees until the anticipated moment of reveal.
Similar to Amagansett, there are lovely little shops to check out around the town center. If visiting in the Winter, you can get souvenir sweatshirts at any of the surf shops or White’s department store/pharmacy before heading down to the beach.
A longtime proponent of the benefits of cold-swimming, I always come prepared to take a polar plunge in the Winter months. And when there’s no one there, you can pull up directly in front of the beach access and park practically on the sand.
When you’re all tired out from beach walks and cold swimming, options for lunch are just around the corner.
Our go-to’s include:
779 Montauk Hwy, Montauk, NY 11954
Serves up wraps, smoothies and salads among other organic fare for Breakfast and Lunch. Vegan and GF options available. This gem even includes a market where you can pick up snacks and grocery items.
28 S. Etna Ave, Montauk, NY 11954
A health food mecca famous for frequenting celebrities in the Hamptons, namely Gwyneth Paltrow when she’s in town. I’ve tried the acai bowl, a few of their smoothies and of course gluten-free options on their wraps and sandwiches, all of which I’d order again.
*Joni’s is closed in the Winter months (reopens April 1st) making April the ideal time for a trek out East
There are also loads of seafood joints and restaurant-style dining in the village if you prefer that route. Check out the likes of 668 The Gig Shack, Montauk Circle Burger, and MTK Lobster House.
For the coffee-obsessed, Hampton Coffee Co. is right on Montauk Highway in the town center, and Left Hand Coffee is off S. Edison St., a bit closer to the beach. Sipping iced coffee and exploring small stretches of beach just go together, don’t you agree?
Third stop: the Lighthouse
If you’ve made the drive this far, you might as well round it out for an even better view of the Atlantic waves. The Montauk Lighthouse is not to be missed! Even if you don’t go into the Lighthouse for a tour, the views from the lookout points are well worth it. You can watch the surfers from the cliff, or surf here yourself. Montauk is the crème de la crème for surfers on the East Coast and has been named one of the best surfing towns in the US by Surfer magazine.
Fourth stop: Sag Harbor
As you begin your drive back West, take your time!! I recommend making a little detour up to Sag Harbor, another small seaside town that makes up part of the Hamptons. Stop in at Grindstone to pick up some of the most mouth-watering donuts you could possibly have. They close at 4pm, so it has to be timed well, but will more than pay off after your first bite. There’s a little bookstore next door worth a gander, especially if you have a taste for coffee table books. Sag Harbor Books has one of the biggest collections of coffee table and picture books that I’ve ever seen (think Gucci, Vogue, Assouline travel, TASCHEN art, etc.), along with an impressive display of rare books, and shelves of encased editions of classics.
Next, you might walk along the docks and see some truly beautiful boats moored in the bay. They’re usually tied up by April, but if you’re there in March or earlier, you’ll just have to enjoy sitting on the docks for the peace and quiet, rather than the luxurious yachts and boisterous people. I often take my coffee from Grindstone and a book from Sag Harbor Booksellers over to the benches on the dock and stay a while to read. I’d definitely recommend!
If you’re feeling the need for another sweet treat, Buddhaberry is a funky little place on Main St. with an array of froyo, smoothies, milkshakes, and even coffee/teas. They’re open late for those of us who stick around past sunset.
Fifth stop: Foster Memorial Beach
Speaking of sunsets, this strip of sand on the bayside is known for being a popular spot for catching them. A short drive from Sag Harbor village, you can park right in front of the water and even stay in your car if it’s chilly. We usually take our donuts and a blanket out to the sand for a little sunset picnic. On a clear night, the water is calm enough to be mistaken for a still lake; you won’t believe the stunning reflections on the water as the sun drops below the horizon and peach pink clouds turn violet to indigo.
Closing it out:
Drive back to the city after sunset to conclude your day trip out East, or find a little place to stay the night!
Still in need of a late dinner on your drive back? Local Burger in South Hampton is a godsend for those times when you just need to indulge. Looks can be deceiving because this walk-up joint packs a punch that will not disappoint. If you need some help deciding what to order when you get to the window, their chicken sandwich and Cajun fries have been known to delight. Here’s to a dinner that will keep you full and satisfied for the whole ride home.
And that’s a wrap!
Walking the docks, stumbling into quaint booksellers and boutiques, sitting in a warm car parked on the beach, watching the waves come rolling in and washing back out again. It dawns on me, there’s just something about North-Eastern beach towns in the off-season. While they rest, I feel something inside of myself awaken.
So, next time NYC is feeling a little colder and more crowded than you might like, head out East for some fresh air and an awakening of your own.
