An Artist’s Guide to the Hamptons in the Off-Season



There’s a different rhythm to the beauty of the Hamptons in the off-season. It’s easy to see why so many artists, from Jackson Pollock and Robert Dash, to Winslow Homer and contemporaries like Eric Fischl and Chuck Close, stuck around for the entire year. The fall and winter on the east end are mystical, and though the pace of life slows, there’s plenty to see and do. Read on to check out my top recommendations for creatives to enjoy in the “off-season”:

The Pollock-Krasner House

As the founder of design company Watson & Company, I lead a team of creatives, designers, producers, strategists and entrepreneurs, so I’m always looking for creative and artistic inspiration. I love that Warhol, Pollock and de Kooning were all out here working at one point, and I love thinking about the creative processes they went through and how the atmosphere impacted and directed their thinking. If you’re down in Springs, see Pollack’s old art studio at the Pollock-Krasner House on Springs Fireplace Road. Inside are all the furnishings and artifacts that were in the house at the time of Krasner’s death in 1984. They’ve also kept his jazz record collection, his personal library, and an original late 1930s painting by Pollock on display. The house was built in the late 19th century, so it gives you a sense of what farmers’ and fishermens’ homes in Springs were like back in the day.

Mashomack Preserve hamptons

Mashomack Preserve on Shelter Island

Just a short drive and a ferry ride away, Mashomack Preserve on Shelter Island is a highly inspiring environment for any artist who wants to submerge themselves in nature and encounter tranquil pockets of wood and terrain. It’s the perfect place to take a solitary walk for some moments of contemplation or meditation. Afterwards, grab dinner at the Vine Street Cafe. It’s one of the best restaurants on Shelter Island – a small, charming dining house that uses fresh local ingredients.

The Hamptons International Film Festival

One of the greatest things about fall in the Hamptons is the Hamptons International Film Festival. Taking place in October every year, the festival showcases emerging filmmakers and new voices, and some of the best offerings of contemporary film from around the world. The selections take a global perspective and make a point of presenting a number of diverse ideas. Tickets are easy to get in advance online, and the screenings happen at the East Hampton Cinema, as well as at Guild Hall.

Guild Hall Hamptons

A Cultural Gem - Guild Hall

Speaking of Guild Hall, it is a visual and performing arts center based right in East Hampton that has a rich schedule of events and programs throughout the year. It’s also conveniently steps away from the Jitney stop in East Hampton Village and the historic 1770 House restaurant (for the most delectable burger). They have 2,400 works in their permanent collection, from paintings, sculptures and photography, to videos and installations. Their collection includes notable Hamptons artists like Richard Prince, Eric Fischl and Max Ernst, and they have around eight-10 exhibitions every year in their gallery space. Local contemporary artists who live in the region, like April Gornik, Barbara Kruger, Richard Prince, Cindy Sherman, and Taryn Simon all participate in the events and programs there. They also recently started screening live HD productions put on by the Met, so you can catch national theater and opera in a small town setting!

Parrish Art Museum Hamptons

Galleries Galore

The East End has no shortage of art galleries, and when the crowds leave in late August, it’s a wonderful time to catch a quiet show. From the Eric Firestone Gallery in East Hampton, the Grenning Gallery in Sag Harbor, the Southampton Arts Center and the Parrish Art Museum, there are plenty of opportunities for art viewing. The Parrish Art Museum is an extraordinary sight to see for any architecture or design fanatic. Designed by the internationally acclaimed firm Herzog & de Meuron, the museum sits on 14-acre site in the hamlet of Water Mill. The exhibitions are focused primarily on work by local artists from the South and North shores of Long Island. In their permanent collection, there are more than 3,000 works of art from the nineteenth century to the present, including pieces by local artists like Chuck Close, John Chamberlain and Eric Fischl.

Tutto Il Giorno Sa Harbor

Good Eats (And Visual Treats)

There are myriad places to grab a bite in a delightful atmosphere, but one of my favorites includes Donna Karan’s new place in Sag harbor, Tutto Il Giorno. The restaurant feels like a cozy and elegant living room with soft, sleek furnishings in neutral colors and raw, cement walls, covered in artwork by Gabby’s father, Steven Weiss. If you’ve never been to Tutto Il Giorno’s Tribeca location, you’re in for a real treat. The menu has a contemporary take on pasta and seafood and you’ll feel like you’re in Naples.

American Hotel Sag Harbor

Another favorite is the American Hotel in Sag Harbor. The upscale hotel, dating from 1846, is right on historic Sag Harbor Main Street and just a few minutes from the harbor. The main dining room with its dark wood is cozy and elegant and the front porch, with wooden tables underneath a white portico, is somewhat of a landmark in the town, having seated politicians, rock stars and celebrities over the years. And when your creative juices aren’t flowing, their martini usually does the trick.

William Watson FeatureThere are a plethora of options within reach when you’re in the area, whether it’s a cozy restaurant or a historical site with a story to tell. No matter the time of year, setting or ambience, the beauty of the Hamptons, especially in the off-season, is that you can find inspiration in the most unexpected of places.

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