The Perfect Hamptons Memorial Day Weekend Itinerary

Wondering how to spend your long holiday weekend? Head east.

Wondering what to do with your 3-day weekend? Head east. • Photo courtesy of Wolffer Estate Vineyard

It’s finally here: The unofficial (and yet somehow official) start to summer. Which means you’re probably daydreaming about the Hamptons. Which means you should come up with a game plan—and stat. Look no further than this proposed itinerary for the Best Memorial Day Weekend of All Time.

Where to Stay: 

Hamptons haunts sell out early, especially over holiday weekends. If you’re having trouble deciding where to stay, here are some personal favorites east of the Canal:

Day 1: 

Daybreak Bites

Breakfast (and lunch) before beach. Stop by Pierre’s Market in Sagaponack for a grab-and-go breakfast sandwich and picnic essentials for solid holiday beach going. Once you’ve finished foraging, follow the road toward the slip of blue that is one of the Hamptons’ best beaches: Sagg Main. Unlike many of the beaches on eastern Long Island, Sagg Main allows non-residents to park and pay by the day. The sandy beach is peppered with impressive dunes and even more impressive waterfront homes.

Get Your Buzz On

Once the sun has waned a bit, take advantage of Sagaponack’s other main attraction: Wölffer Estate Vineyards. A sprawling back bluestone patio overlooks acres of grapevine. You can order red, white, and rosé by the glass and by the bottle (or opt for the winery’s dry seltzer, sold in small splits), as well as snacks like cheese and charcuterie plates are available. It’s the perfect place to while away a warm afternoon.

Sundowner

After a shower and a change of clothes, head to East Hampton’s waterfront, tucked away on Three Mile Harbor Road in Springs. Bay Kitchen Bar has a sprawling deck that overlooks the water and serves fresh seafood and potent cocktails with one of the best sunset views in the Hamptons. Once you’ve filled your belly, head down the road a bit to Moby’s, now housed in the former East Hampton Point space, where a massive waterfront restaurant and bar turns into a late-night party scene.

Day 2:

It's Sunday night, you know what that means! #montaukpearls for a buck-a-shuck!

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Hangover Helper

Skip breakfast and opt for the ultimate cure of a greasy spoon lunch, preferably at the satisfying and ever-crowded Sip N Soda (diner cheeseburgers at their finest). You can pick up a few snacks for the beach at the Southampton Farmer’s Market (Sundays, 9 a.m. to 1 p.m.) before heading to Sag Harbor’s slip of bay perfection: Foster Memorial Town Beach (otherwise known as Long Beach). Day parking passes can be purchased on site for $40. The beach is nearly two miles long and features gentle, warm, and shallow bay waters, perfect for lounging, swimming, and paddle boarding (bring your own).

Oysters, Oysters, and More Oysters

Just down the road from Long Beach is Bell & Anchor, David Loewenberg’s year-round Sag Harbor restaurant. On Sunday nights, the restaurant sells Montauk Pearl oysters for $1 apiece, and, to quote Mean Girls, the limit does not exist. Indulge in bivalves—and the double-thick pork chop, if you’re feeling saucy—along with a glass of bubbly. Or two.

Sweet Tooth

Head into town for your choice of desserts. My heart lies in the brioche-based donuts at Sag Harbor’s Grindstone, which is owned and operated by Chef Michael Symon’s stepson Kyle. But if ice cream is your poison, Big Olaf’s is right down the street and will happily scoop you an oversized waffle cone topped with whatever crazy topping you happen to be craving.

Day 3: 

Fully Baked

Head over to Carissa’s Bakery in East Hampton for a gruyere and ham croissant (or any other manner of painfully delicious treats) and, while you’re there, stock up for the week ahead. The olive ciabatta makes a particularly good Hamptons parting gift, but I never leave the bakery without a French ham, butter, and cornichon sandwich, served on fresh baked baguette. Save it for later—or tell yourself you will and eat it in the car.

Botanical Beauty

LongHouse Reserve, the incredible, 16-acre sculpture garden and private park, is a must-visit on a nice day. Depending on the blooming season, you’re bound to encounter all kinds of botanical joys (my personal favorite is the fuschia-to-scarlet azalea walk, which blooms fire pink only one week a year). Bring a blanket and lie out on the grass for as long as you like. Technically, the reserve is only open on Wednesdays and Saturdays, but in-season appointments are accepted every day of the week except Sunday.

Go Green

Before you head west, stop by Balsam Farm’s farm stand, where you can pick any manner of fresh fruits and vegetables. Balsam also carries fresh pies, soups, sauces, pickled and preserved goods, fresh cheese, yogurt, pressed juice, and practically everything else you can think of, offering ample options for the trip home and for at least a week’s worth of groceries.

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Hannah Selinger

Hannah Selinger is a freelance food and wine writer and sommelier living in East Hampton. Her work has appeared in the such publications as the New York Times, the Washington Post, and RawStory.com. She is the wine columnist for the Southampton Press.