Hamptons in the Fall: Out of Season, Never Out of Style

Hamptons in the Fall

Fall is a wonderful time to visit any of the Hamptons—the lovely towns on the eastern end of Long Island, New York.

As we headed into the Hamptons on Route 27, a mostly two-way road, the trees were just beginning to turn those brilliant crimson and yellow colors. 

Local gardening shops all had jewel-tone mums, and pumpkins were at every farm stand. Traffic was light, and reservations were plentiful for spa treatments and restaurants.

We made our base at the furthest point of the peninsula, in Montauk. 

Montauk is a picturesque coastal town with stunning Atlantic Ocean vistas, even on cloudy and cool days. When visiting this part of the Island, it’s important to recognize and honor that we are on the traditional territory of the Montauk Tribe of Indians. (Visitors can learn more about the first people at the Montauk Indian Museum.)

Living large in Montauk

Hamptons in the Fall: Gurney's Resort in Montauk
Gurney’s Resort in Montauk

We stayed at Gurney’s Resorts, a luxury property in Montauk with a unique blend of relaxation, stunning ocean views, and top-notch amenities. One of the grandest hotels developed after World War II, it started out as Gurney’s Inn and has become an extensive, luxury resort. 

Our two queen-bed room offered a walk-out terrace right on the beach. With the door opened, the sound of the surf was extraordinary. Walking on the beach calms the soul, with opportunities to commune with the seagulls and pick up driftwood. 

And when it rained, we spent a day at the resort’s Seawater Spa and sampled their massages and facials. Ask for Alba for your facial; she was outstanding. The spa’s signature feature is its unique indoor seawater pool, not to be missed.

Coffee and croissants in the lobby started our mornings. Breakfast at Tillie’s included crab cake egg benedicts and Blueberry pancakes. After a nice dinner at the resort’s Scarpetta Beach restaurant (which included lobster spaghetti and Cacio e Pepe ravioli to die for), we enjoyed a nightcap at the outside bar, seated comfortably around a roaring gas fire pit. 

Blueberry pancakes at Tillies's
Blueberry pancakes at Tillies’s

Gurney’s takes its pet-friendly reputation seriously as we discovered when the table next to us at dinner featured two humans and two pugs (in chairs). We also encountered the latter next day at the spa, when their owner was attempting to book dog massages and facials. Fortunately, the resort’s policies didn’t extend quite so far.

Culinary finds beyond the resort

Beers at Montauk Brewing Company
Montauk Brewing Company

There is also abundant eating, drinking, and tourism outside of the resort. 

An hour at the Montauk Brewing Company makes you feel like a local. The Pumpkin Ale is a fall must-taste. 

We also enjoyed dinner at Harvest on Fort Pond. It’s a farm-to-table concept with seasonal dishes prepared with locally sourced ingredients. Another great dining spot is South Edison, with crispy duck legs and shrimp tacos.

Things to see and do

Montauk Point Lighthouse in the fall
Montauk Point Lighthouse in the fall

Beyond the local culinary pleasures are the many local sights. Preeminent among these is the Montauk Point Lighthouse, standing proudly at the easternmost tip of Long Island. It is a historic landmark and a symbol of the region’s maritime heritage. 

Lobster roll lunch in Amagansett
Lobster roll lunch in Amagansett

Dragging ourselves away from the pleasures of Montauk, the other towns and villages also had much to offer. No visit would be complete without a stop at the Lobster Roll in Amagansett. Buttery lobster and tasty drinks filled us up over the top. We tried the Chocolate Egg Cream—a cross between a soda and chocolate milk—and found it delightful. Almost across the street is The Clam Bar, recommended by many locals for their lobster rolls. Apparently, the competition for the “best” in this category is keen.

Sag Harbor and East Hampton

Sag Harbor and East Hampton both offer opportunities for great window shopping and strolling, both with very different vibes. 

Sag Harbor is a picturesque village with quaint streets and charming stores. East Hampton is the high-end shoppers’ nirvana with big-name boutiques.

Both offer top-notch bookstores: BookHampton in East Hampton and Sag Harbor Books. Another selling point for off-season travel is that every store seems to have a great sale in progress.

A “taste” of Long Island Wine Country

Wolffer Estate Vineyard
Wolffer Estate Vineyard

In recent years, New York has burnished its reputation for outstanding wines, and the North and South Fork areas on Long Island don’t disappoint. 

With only a relatively short amount of time to explore, we decided to spend a couple of hours at Wölffer Estate Vineyard, a picturesque destination on the South Fork. Not all of the tables were taken, but it was quite busy.

We sat on their heated outside terrace and couldn’t pass up the hot brie and baguette to go with our Rose Cider and flight of New York wines. We especially enjoyed their signature Chardonnay and brought a bottle home.

Best of New York Flight
Best of New York Flight at Wolffer Estate Vineyard

The pleasures of the Hamptons in the fall

While prices are much lower off-season, the cost of a Hamptons weekend can still be pricey—but worth it—for the sound and smell of the ocean and the relaxing vibe of the area. 

What’s not to like about fewer people and better prices? We will be back.

*Guest contributor Ali Webb, PhD is adjunct faculty at the University of Michigan and Columbia University. Her long career in strategic communications offered many opportunities that have inspired her lust for domestic and foreign travel. She has written a bi-monthly Sunday travel column, The Indulgent Traveler, for a Gannett daily in Michigan and now contributes to other travel websites. 

All photo credits: Keith Kehlbeck



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