One of my favorite of the weekend trips Aron and I took when we lived in New York was a September one to Montauk to celebrate my birthday. It was full of lobster rolls, clam shacks, and I recall the town had a low-key surf vibe that made me feel like I’d gone home to California in a setting that felt nearly New England. That said, we stayed in a completely disgusting motel and talked about one day going back and doing it better.

We finally got our chance! We tacked four nights onto our New York stay, renting a car from Manhattan with a JFK return, to drive out to “the end.”

It took us a long time to get out of the push-and-pull of the New York City metro area, so we first found ourselves checking Yelp reviews for the best diners off interstate 495; we landed at Premier Diner in Commack. Those classic Long Island diners always surprise me. In California, if you walk into a diner that looks out of the 1950s, you’ll find milkshakes and burgers with a side of juke-box (think Ruby’s), but these places have enormous menus with high-priced steaks and french onion soup next to pancakes. This one had beet salads that arrived on the table when the service began. Our waiter seemed straight out of a movie, tucking a pencil behind her ear and talking across the room to regulars. “That’s all?” She dismissively asked when I chose the soup.

We got back on the road and soon the lawns grew wide, and we spotted a few rabbits and deer in the shadows. Then, suddenly there would be a row of posh shops—we’d made it to the Hamptons.

Montauk is the last of the towns along this stretch of Long Island—the very tip—so it was dark by the time we found the driveway leading to our Airbnb. Aron tucked the kids in, while I went back out to pick up groceries. We were all excited to get our bearings come morning.

We’d chosen a small cottage in Outrigger, with a deck facing the water. A large lawn led down to a private beach on lake Montauk. We knew from our first visit that it we enjoyed going to Ditch Plains and Gin Beach, so we thought best to look for something on the east end of town.

The rain had been heaviest on our driving day, but continued in the morning. No matter, it didn’t keep the kids from rushing down to the beach to get busy looking for treasures.

I have this feeling they would have wandered up to their waists before noticing—they were so focused on the shells, shark-egg casings, and various remains that formed their collection. They even found a horseshoe crab—especially exciting after learning about them at the American Museum of Natural History. They were around before the dinosaurs!

With a sunny day on the forecast ahead, we knew we’d want to spend all Saturday at the beach—so this seemed the best time to get in the car and backtrack a bit toward Amagansett to Lunch, AKA The Lobster Roll.
If memory served correctly, they served up one of the best lobster rolls ever—and it didn’t disappoint. I had the lobster salad roll: the Maine-style, with buttered and toasted bun filled with lobster meat tossed with mayo and, in this case, celery mixed in for added crunch. Aron ordered the Connecticut-style: simply warm lobster with butter, served with a bun. Allegiances run deep when it comes to these preferences, but pssssst… both are wonderful.

We played Uno, ordered steamers, and watched the rain fall; we also realized we were seated at the table from the first scene of the show The Affair. Uh-oh.

I’m not sure what they were really, but the kids optimistically tried to peddle some mini plums (“minie plumes”) they found. Later, when we were packing up the cabin and thinking back fondly on our week and on our sweet kids’ stage in life, I looked back at that napkin’s “It’s a really good season. Extra sweet,” and it took on a new meaning. (It sure is, kiddo.)

The sun finally broke through the clouds in the afternoon and the promise of sunny days stretched before us. We’d fondly recalled a meal on the deck at Duryea’s—a Montauk classic for years—where one ate lobster on paper plates and ordered at the counter. Apparently Perry Duryea Sr. bought the place, a boathouse with a long pier on Fort Pond Bay, back in the 1930s and recently sold it. Its transformation into a slicker, more Hamptons-y version of itself has ruffled a lot of local feathers. We could see why, but it still made for one of the most beautiful evenings of the trip, with a ridiculously gorgeous summer-solstice sunset.

We went early and had a great table right by the pier—but it did fill up quickly as the sun went lower. Kids played on the beach beside the restaurant, and watched a swan swim about with a grey cygnet. We watched many arrive using Ubers or Lyfts, but I hear that you can paddleboard (or dock your boat) to get there, too.

It was the perfect way to mark the solstice!

We met one family on the beach who had been coming every summer for years and they suggested that another perfect evening could be spent having a clam bake on one of the beaches, but I can’t recall which he suggested.

The next morning we packed up for the beach and then decided to grab an early lunch in town, first.

The folks from Tacombi, in Nolita (which we didn’t go to on this visit to New York) opened up La Brisa a couple years ago in the middle of Montauk village, so we stopped there. I love their seafood tacos! They happened to be right next door to a summer pop-up shop with a really great clothing selection, too. Pop-ups happen all over the Hamptons in the summer, so if you’re looking for good shopping, I’d suggest doing a web search before a trip.

I actually only had one shop wishlisted during our stay in Montauk—a tshirt shop called Montauk Mainstay “born out of nostalgia for fluke fishing on the Lazybones with my dad and brother, early morning coffee and egg sandwiches from the Bake Shoppe, and family lobster roll dinners at Duryea’s.” They have a great selection of t-shirts in kids’ sizes and I’m always looking for good boys’ options.

Actually, the spots for which they have designed their shirts reads like a pretty good guide for a visit—all the classic spots, like John’s for dipped ice-cream cones, Lazybones for fishing trips, the Clam bar for ‘chowdah,’ and the Montauket for sunsets and drinks by the lighthouse.

Ditch Plains beach was about a mile from the cottage, which was perfect since parking passes are for residents only during the high season. Ditch Plains is the classic Montauk surfing beach, so it had been suggested that we might like Gin Beach better—calmer waters—but it wasn’t too rough that day and I just preferred the setting.

Aron dropped the kids and I off with our things, then parked the car and ran back to meet us. In that time, the kids had already made a bunch of friends and built an entire moat system around a castle.

The water was too cold for me, but everyone else briefly braved it. Most who were spending more time in the water (surfers, for example) wore wetsuits.

I felt so lucky that we had gotten that beautiful, sunny day to enjoy the beach!

The Ditch Witch is another one of those most-beloved Montauk traditions: the small trailer-kitchen parks at the end of Otis road (the second parking lot) and serves breakfast burritos and wraps, juices and coffee, etcetera. We had to stop before the walk back home.

For dinner, we stayed close to the cottage and drove over to Gosman’s Dock for a lesson in eating fresh steamers—and for more lobster. There’s a clam bar and a restaurant and the Gosman’s complex seems to extend forever. Kids can play on the beach, but watch out if they leave any food unattended—the seagulls are on their game! The marina has some shops and we took the kids to Ben & Jerry’s for their first time before watching some of the sunset from the beach.

Apparently it’s also the place to go to the Fish Market, where you’ll find a mix of local seafood from the boats that sit in the harbor just outside alongside produce from nearby East End farms. I didn’t see any taffy stores, but it sure seems like the kind of marina where you’d find those, too.

We were sorry we didn’t have longer to spend in Montauk. The next day was a Sunday, so we didn’t want to linger too long and get stuck in all of the returning traffic into the city.

If you’re planning a trip and are looking for more restaurant suggestions, I’d send you to that Mainstay page first, or to this list on the Infatuation. There’s also a Goop guide. But the best of all of it was the sea-salt tinged air and the lazy mornings looking out at the lake.

Our host also suggested: the walking trails around Big Reed Pond and one east of town along the Dunes on 27 called Shadmoor; a visit to the Lighthouse at the “The End”; and Montauk Downs State Park for their public golf course, tennis courts, and outdoor public pool. For food, her top picks were South Edison and The Harvest—and of course sunset barbecues at home. Maybe next time!

We drove directly from Montauk to JFK, pulling over just a couple of times—once for another cookie from the Hamptons-outpost of Levain bakery, and once to see someone catch a fluke in Hampton bays. I’ve heard a good rule of thumb is that traffic will start earlier on bad-weather days and later on good-weather days (when everyone tries to squeeze in more beach time), so the sunshine served us well.

It was a great end to a wonderful week!

Have you stayed in Montauk—or elsewhere on the South Fork of Long Island? Any suggestions?

P.S. Our first visit to Montauk. Strawberry picking on Long Island. A day trip to Fire Island. And the first half of our week, in New York City.

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