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Fall is an ideal time to make a trip to East Hampton. (Photo Credit: istock/Meinzahn)

Long Islanders live in an area where others vacation. Hollywood descends on the East End each summer for soirees and beach days. New York City residents come to the North Fork for wine tasting and pumpkin picking. It’s a point of pride and a curse, as any Islander who braves the summer traffic can confirm. 

As the hectic pace of the summer season winds down, fall makes an ideal time to take a break and become a tourist in your own backyard. (And if you’re coming from elsewhere, it’s a great time to find deals and beautiful scenery for you, too.)

There’s plenty to do — here are three itineraries for the easiest of nearby getaways.

Something Out East

The South Fork, moreso than the North Fork, sees its high season come to a close on Labor Day Weekend. Tumbleweed Tuesday rolls around, and suddenly, Montauk Highway becomes a main road and not a parking lot. 

But it’s everyone else’s loss because the Hamptons are in all their glory come fall. The foliage is a leaf-peepers’ paradise, and there are even a few farms to engage in the time-honored pumpkin-picking tradition. 

Start your day at a hidden gem. Estia’s Little Kitchen, a tiny roadside cafe, is serving breakfasts with a Mexican-meets-Hamptons twist. Ingredients are sourced from local farms like nearby Milk Pail, and up-Islanders have found themselves dreaming of the egg sandwiches. 

Parrish Art Museum’s annual Midsummer Party is one of the signature events on the annual summer social calendar. But the museum, which you’ll first notice for the two giant Roy Lichtenstein sculptures that tower over the front lawn, continues to showcase world-class art year-round. A Lichenstein exhibition, History in the Making, is running through Oct. 24 and provides a look into his early works. Tomashi Jackson: The Land Clam focuses on the historical and contemporary experiences, such as agriculture and transportation, of Black, Indigenous and Latin American families on the East End. 

Discuss what you learned and loved at Parrish over lunch at Provision’s Natural Foods four minutes away in Water Mill. Cafe menu items include grilled chicken with crunch fall apple slaw and aged cheddar or a vegan chili that sticks to the ribs in all the right ways.

Duck Walk Vineyard is a popular stop on the North Fork, but it also boasts a Hamptons location. The Vidal Ice wines, produced from grapes actually frozen on the vine, are a sweet treat. If you have time, it’s worth stopping at Hank’s Pumpkintown for a pumpkin and apple picking — or at the very least, an apple cider donut. ’Tis the season. But save room for dinner at Calissa’s, where the Mediterranean cuisine is light and fresh. The beet hummus and crispy calamari are popular choices.  

Rest weary legs at Mill House Inn, a luxury B&B in East Hampton. There’s a fireplace in every room— ideal for a cozy fall evening. 

Something Small Town

Looking for a dose of autumn quaint? The Long Island region is home to plenty of areas with a small-town charm, complete with bustling Main Streets and mom-and-pop shops that continue to find creative ways to pivot during the pandemic. 

Several towns and villages within driving distance along the South Shore of Suffolk County fit this bill. Begin with breakfast at The Shed in West Sayville. The interior of the space is bright and airy, with white-washed walls accented by poppy art. On the menu, you’ll find comfort food brunch favorites like a breakfast bowl with two poached eggs, avocado and home fries and Belgian waffles. From there, head to Bellport. The idyllic-but-exclusive setting (residents have access to their own beach on Fire Island, Ho-Hum — ho-hum, indeed). Peruse shops along South Country Road, like Cooper Beech, The Bellport General and The Storefront.

Bellport’s main street, South Country Road, is full of charming shops and restaurants. (Photo Credit: Alison Buck/Temperance Hall)

Before leaving, see if you can do an early check-in at Bellport Inn, where you’ll be staying the night. The hotel, which dates to 1889, sits in the heart of the village. But the tranquil gardens with grapevines and blueberry bushes provide an escape from the bustle.

Next, you’ll head to Bay Shore. The downtown, which has experienced a resurgence over the last half-decade, is home to an array of unique restaurants, including Tullulah’s. The ambiance inside is industrial-meets-speakeasy, with dimmed lights and exposed wooden beams. Popular lunch dishes include creamy Mac ’n cheese and grilled cheese sandwiches. Walk it off and get sand in your shoes at Robert Moses Beach. The fields will be less crowded, giving you space to sprawl out and enjoy the perks of living on an Island.

Once you’ve gotten all the sun, sand and sea you can handle, head to dinner in Babylon Village. Barrique Kitchen & Wine Bar, a tapas-centric wine bar, boasts beer, wine and spirits tastings as well as a tapas menu that allows you to mix and match throughout your meal. Think a creamy burrata that melts in your mouth, Oktoberfest-worthy pretzels with baked brie and scrumptious veal meatballs. 

Something Cultural

With New York City in our backyard, it can be easy to overlook the arts, culture and history right here on the Island. But that would be a mistake. From Gatsby-style mansions to theaters hosting performances that will leave you begging for an encore, there’s plenty to learn about your home region.

But no one learns well on an empty stomach, so start your day with brunch at Hatch in Huntington. The bright interior with yellow chairs and a neon sign that says, “My Happy Place” above the open kitchen is like natural caffeine. But go ahead and grab a coffee too. It pairs perfectly with the huevos rancheros. From there, head to Oheka Castle. The famed 1919 Gold Coast mansion has gorgeous formal gardens made for exploring. See if you can drop your bags there — you’ll be sleeping like a royal tonight. (Bonus: Ask about the in-room massages). 

The Oheka Castle (Credit: Phillip Ennis)

Coindre Hall, a 15-minute drive away, is next on your list for the Gatsby portion of this fall getaway. The French chateau, a National Historic Landmark built in 1912, exudes a medieval charm. It’s also a park with sweeping views of Huntington Harbor.

You’ll re-fuel at Besito, which has put an upscale twist on Mexican grub with iron skillet tacos and guacamole so good you’ll want to plan on asking for seconds. Then, head to Hecksher Museum of Art. The current exhibit, Eclipse of the Sun, showcases political art and includes depictions from World War I and Nazi Germany. Reservations are recommended. 

Talk about what you saw — or go back to not mentioning politics — over dinner at Northport’s Whale’s Tale. The sweeping waterfront views and seafood to write home about provide a welcome respite from current events and the dropping temperatures. The spot is also a short distance from the John W. Engeman Theater at Northport. The local gem on Main Street is putting on Smokey Joe’s Cafe through Oct. 31, and you’ll be tapping your feet and dancing in the aisles to showstoppers like “On Broadway” and “Stand by Me.”