The Jim Phelps Guide to the Hamptons: A Legacy of Good Living
They say you can tell a lot about a man by where he chooses to break bread. If that’s true, my father, Jim Phelps, was a man of warmth, impeccable taste, and a deep-seated love for the simple joy of a long lunch and a perfect view.
It’s been three years since he passed, and while the Hamptons landscape is always shifting—new storefronts, new crowds, new trends—the places he loved remain the anchors of my map. When he visited, the world felt a little more vibrant; the wine tasted a little crisper, and the sunsets over the water felt like they were performing just for him.
This isn’t your typical "hot list." This is The Jim Phelps Guide to the Hamptons. It’s a collection of the haunts where he laughed the loudest, tipped the most generously, and taught us that the best seat in the house is any seat shared with family.
As we travel from West to the East, I invite you to pull up a chair at my dad’s favorite tables.
Hamptons Hippie Lithography Co. ©2026; HH Flamingle Wallpaper, Ferrisland “Vintage” Picture Frame
Atlantic Seafood, Center Moriches, NY⚓︎ Technically just outside the Hamptons gates, but it was a mandatory stop for my Dad. Some of my favorite last photos of us were taken right here, smiling under that iconic giant shark head. It’s a reminder that sometimes the best memories aren't at a white-linen table, but standing on a gravel lot with a bag of fresh fish and the person you love most. My personal faves are the Lobster Bisqué & the baked clams.
Hamptons Hippie Lithography Co. ©2026; HH Colorful Toile Wallpaper, Williams Sonoma HOME Picture Frame
Trumpets on the Bay, Eastport, NY⚓︎ This was my Dad’s "viewing deck." He loved the 90’s country club vibe here—it felt classic, comfortable, and unpretentious. We’d walk over from my house & sit for hours watching the boats drift by. It wasn't just about the great food; it was about the pace of life. Trumpets always felt like the official start of "vacation mode." Fabulous anti-pasto plate & crab cakes!
Hamptons Hippie Lithography Co. ©2026; HH Camo Sea Wallpaper, M aison Flaneur Picture Frame
The Little Gull Cafe, Speonk, NY⚓︎ Tucked away at the Speonk Train Station, this is quite possibly the cutest lunch spot in existence. It has that old-world charm that my Dad appreciated… and of course that magical velvet Elvis painting that literally feels like he’s watching following you with his eyes. There’s something whimsical about a train depot lunch—the coming and going of travelers while you sit still and enjoy the moment. Amazing mile high tuna melt on homemade challah bread! Holla!
Hamptons Hippie Lithography Co. ©2026; HH Watercolor Wallpaper, Vintage Picture Frame
Margarita Grille, Westhampton Beach, NY⚓︎ This was Jim’s Friday night go-to. He was a master of the "people-watch," and there was no better vantage point. With a margarita in hand and a prime seat on the patio, he’d soak in the village energy. It was fun, lively, and exactly where he wanted to be to kick off the weekend. The Watermelon Margs are perfection!
Hamptons Hippie Lithography Co. ©2026; HH Daytripper Wallpaper, Urban Outfitters Picture Frame
Beach Bakery Grand Cafe, Westhampton Beach, NY⚓︎ We had a very funny, highly memorable lunch here. The place itself is a Westhampton institution, but for us, it was the location of a legendary performance. While we were eating, we realized we were next to a large table of little old ladies, and as we listened, it became clear they were all competing in a high-stakes game of one-upmanship about whose child was the most successful. My Dad thought it was the absolute funniest thing ever! It wasn't just a bakery; for us, it was a stage where he found genuine, unfiltered joy in the quirks of Hamptons life. Another fabulous tuna melt too!
Hamptons Hippie Lithography Co. ©2026; HH Peconic Picnic Wallpaper, Mariposa Picture Frame
SHOCK Ice Cream, Westhampton Beach, NY⚓︎ No one had a sweet tooth like Jim, and SHOCK was the only cure. Homemade, rich, and a total WHB staple. No trip to the village was complete without a scoop (or two). Watching him tackle a cone with pure, childlike joy was a gift in itself. So many fun flavors but I’m partial to the homemade chocolate peanut butter!
Hamptons Hippie Lithography Co. ©2026; HH Critter Wallpaper, FBM Picture Frame
Joe’s American Grill, Westhampton Beach, NY⚓︎ Our Saturday tradition. After evening Mass at Immaculate Conception, we’d head straight to Joe’s. It’s the quintessential American grill—consistent, welcoming, and warm. It felt like an extension of our own dining room, a place where the staff knew you and the food felt like a hug. Back when I was eating meat, I’d get the amazing burger! Now, I love their broad salad section.
Hamptons Hippie Lithography Co. ©2026; HH Postie Wallpaper, Etsy Picture Frame
Dockers Waterside, East Quogue, NY⚓︎ One of Jim’s absolute favorites. We shared so many milestone moments here, most notably my Rehearsal Dinner. Dockers has that magical Hamptons water-front energy where the water meets the sherbet colored sky, that my Dad just loved. The sky there is always majestical & every time I see the sun dip below the horizon there, I feel him with us!
Hamptons Hippie Lithography Co. ©2026; HH Equestrian Wallpaper, Wayfair Picture Frame
Pierre’s, Bridgehampton, NY⚓︎ When we wanted to go on a "classically fun" excursion, we headed to Bridgehampton. Fabulous food, a touch of French flair, and Dad in his element—enjoying the finer things with a down-to-earth flair. Another great burger for the meat eaters out there!
Hamptons Hippie Lithography Co. ©2026; HH Native Flora Wallpaper, Cailini Coastal Picture Frame
SALT, Shelter Island, NY⚓︎ This was one of my favorite days ever spent with him. We took the ferry over, the sun was shining, and the vibe was perfect. We collected seashells on shell beach & hit SALT for lunch after. I’ll never live down the moment I accidentally ordered the "super expensive" bottled water. He teased me about it for the rest of the day—and for years after. He loved to tease, and honestly, I’d pay for a thousand bottles of that water just to hear him poke fun at me one more time. Great fresher than fresh sushi!!
Hamptons Hippie Lithography Co. ©2026; HH Peach Toile Wallpaper, Rifle Paper Co. Picture Frame
John’s Drive-In, Montauk, NY⚓︎ A trip to the End is never complete without a stop at John’s. For Dad, this wasn't just a recommendation; it was a Montauk mandate. There is something about their classic burgers and homemade ice cream shakes that just tastes like a Long Island summer. One of my proudest moments was when my Dad, Allan and I dropped off a piece of my Pop Art featuring the establishment to the owner; Dad was beaming, so happy to visit and share that connection. I’m still a little heartbroken that he wasn't here to see my artwork featured on the Channel 12 news segment about John’s, but I have a feeling he had the best seat in the house for it from heaven. It’s a Montauk institution that will always hold a piece of his heart—and mine. (This is a new JOHN’S artwork featuring my new lithography illustration style and their sparkly NEW sign!)
Looking back at this list, I realize these aren't just restaurants; they are the coordinates of a life well-lived. My Dad taught me that a super expensive bottle of water and a simple bag of fish on a gravel lot are worth exactly the same when you’re laughing with the people you love. The Hamptons change every season, but the memories we made at these tables are permanent. Dad was the original Hamptons Hippie in his own way, navigating the East End with a down-to-earth flair and a legendary sweet tooth. I hope this guide helps you find your own 'vacation mode' and reminds you to find the humor in the little things—even if it’s a table of competitive grandmothers at the bakery.
Go out, eat well, and make a memory today that you’ll still be teasing your kids about in twenty years. Jim certainly would have. So, here’s to the long lunches, the perfectly timed sunsets, and a father who knew exactly how to enjoy them all. Cheers to you, Dad. We miss you at every table. I'm still using your voice as my compass and your love as my anchor.— ⚓︎Sarah (AKA “Prissy”)
