As the summer winds down, fewer and fewer vacation days become available. It’s hard to capture the essence of such a large place, like the Hamptons, in such a short time, so it’s best to take it one place at a time. I’m here to help by detailing a perfect 24 hours in Montauk with a quick tour of my favorite dishes at some of my favorite places. Let’s imagine it’s Friday. Work ends around five, and you just barely make the 5:15 p.m. Long Island Railroad train to The End; this will be a great trip.
Everyone knows how packed the beach town can be, so you’re better off having booked a hotel ahead of time. My favorite is the Surf Lodge, conveniently located right next to the train station. Your first stop? Crow’s Nest. The boutique hotel is known for its manicured cocktails and delicious Mediterranean-style seafood. The location is stunning and the oysters fresh and the chicken kebab perfectly seasoned. Grab a Cana Libre cocktail and relax; the wait can be lengthy, but it’s worth it for this drink made with Caña Brava Panamanian rum, lime, Angostura bitters and Coca-Cola. It really helps heighten your experience as you press your toes into the sand.
. After dinner, hop in a cab to the Stephen Talkhouse, where you are almost always guaranteed a live performance. If you can rally, end the night by watching the moon’s reflection on the water at the Surf Lodge. The place becomes a madhouse on the weekends, so catching it on a mellow Friday night is never a bad idea. Not to mention their late night lobster rolls.
Rise and shine in beachy Montauk, and walk, bike or ride over to Montauk Bake Shoppe, where you will find the best jelly croissants in the world. They are so tasty, regular customers ship them from the East End all the way to England. Make sure you get a couple to-go, and head over to Ditch Plains Beach, known for its amazing surf and great looking crowd. After some R&R with a little beach action, it would be ideal to find something refreshing to cool you down. Just a short walk from town is John’s Drive In, famous for their homemade ice cream that is rightfully rumored to be the best in the Hamptons. John’s is open late, which is a good thing and a bad thing, especially if you can’t resist a good midnight snack, like me.
Last stop? This one is most important, so I saved the best for last: The Clam Bar. It’s not technically in Montauk, but rather in neighboring Napeague. The outdoor oasis is surrounded by bright yellow umbrellas right off Montauk Highway. Many argue that the lobster roll from Lunch is better, but Clam Bar’s soft potato bun speaks for itself. It’s usually safe to try their daily specials and any of the fried fish.
I know I said that was the last stop, but it hasn’t been a full 24 hours yet. You still have two left. What to do? If you can squeeze it in, there’s a hidden gem in town that’s just two years old: Swallow East. The restaurant has fantastic entertainment, funky reggae bands, mac and cheese and scrumptious shrimp tacos. Or head over to West Lake Clam & Chowder House and dig into their banana cream pie. It’s so good, you may explode. Don’t say I didn’t warn you.