Between international bans and state quarantine lists, COVID-19 threw a monkey wrench into travel plans this year: Many of us haven’t traveled much further than the backyard since spring.
But New York has managed to mitigate the virus, making fall ripe for extending your backyard just a little farther. Long Island has long been a region with diverse experiences, from the Gold Coast’s opulence to the sandy South Shore beaches to transporting Shelter Island. With a little imagination, a trip to a nearby town can feel like a great escape.
If you have unused vacation time left, put in for it and consider a Long Island staycation. Let these itineraries be your starting point.
In a year that saw at-home “COVID cuts” become a thing, life has felt anything but elegant. Long Island’s Gold Coast has inspired famous novels and been the backdrop for many a Hollywood films. It gives visitors the chance to go back to an earlier post-pandemic period, when bathtub gin and flapper dresses were all the rage.
For the ultimate Gatsby experience, start the day at Sands Point Preserve, home to the Hempstead House. The home is said to have inspired The Great Gatsby. Taylor Swift filmed her “Blank Space” video there, and it also made an appearance in movies like Malcolm X and Great Expectations. Though tours and access to the Tudor-style mansion itself are suspended, visitors can still explore the 216-acre grounds of Sands Point Preserve. They feature six marked trails that take you through woods, open fields and a pond. Be sure to stop and smell the roses — there are thousands to choose from in the garden with 1,500 rose bushes.
Across the Nassau-Suffolk border sits Oheka Castle in Huntington. Tours of the mansion are on hold, but guests can dine indoors if they please at OHK Bar & Restaurant. No need to dress to the nines, though. There are white table cloths on the table, but the restaurant is upscale casual — a nice pair of jeans and a shirt will do. There’s also an outdoor Piazza with views of the grounds. Lunch favorites include the filet mignon French dip and short rib grilled cheese — both provide the necessary fuel until dinner. If you’re thinking of staying on the Gold Coast an extra night or two, Oheka is also a hotel. The Gatsby suites, inspired by the classic novel, are decorated like they’re straight out of the Roaring 20s (think Victorian chairs and a four-post bed) but with modern amenities like luxury linens and in-room massages.
The tour de Gatsby continues 20 minutes from Oheka at Coindre Hall. The 80,000-foot French chateau is set on a 33-acre park with sweeping views of Huntington Harbor. It’s perfect for a socially distant walk.
Finish the day with dinner at Prime. One of Long Island’s most celebrated surf ’n turf restaurants, the resort-like space includes a cozy lodge and wave bar. Outdoors, diners can enjoy everything from steak to sushi on a deck overlooking the harbor. For guests who would prefer to end the day at home, the restaurant offers both takeout and a prep kitchen, which gives people the ingredients to make their favorite dishes themselves.
Long Islanders can exude a certain type of bravado, but those who have taken time to explore its villages and Main Streets, home to mom-and-pop boutiques, know area boasts a down-to-earth charm. Stony Brook and Port Jefferson exemplify this.
Wake up to some retail therapy at Mint Clothing Boutique. Located in the Stony Brook Village Center, Mint has versatile pieces that make mixing and matching easy — and may inspire you to ditch the yoga pants for a dress-jacket combo for your next Zoom meeting.
Go Greek for lunch at Joey Z’s in Port Jefferson, where the shish-kebabs make for easy for grab-and-go fare, but you can also sit and stay awhile. Indoor dining is open at 50 percent capacity. If taking out, venture down to the harbor, find a patch of grass and chow down. Wherever you dine, a post-lunch stroll around the harbor and through Port Jefferson village would be a pleasant way to spend the afternoon. Pop in and out of shops if you’re comfortable — Amazing Olive has infused olive oils, Pindar’s Wine Store brings a taste of the North Fork to Port Jefferson, and boutiques like Earring Tabu and Fame and Rebel are stocked with an array of styles. There’s also Port Jeff Brewing Co., which will bring back its Boo Brew for the fall (yes, pumpkin is in the recipe).
For dinner, head back to Stony Brook for a sit-down meal at Mirabelle. Set in the historic Three Village Inn, this upscale casual spot serves refined French cuisine like duck breast and American comfort classics, like the tavern burger made with a bacon-onion marmalade. Guests who are tuckered out can inquire about a stay at the colonial inn. Built in the 1700s, some rooms in the main house and six cottages have fireplaces and harbor views.
Something by the Water
During the summer, the South Shore is about sandy shoes and sun-kissed cheeks. Since it’s 2020 and anything goes, there’s no reason that can’t continue into the fall.
Jones Beach is a hotspot each summer for both sunbathing, swimming and rocking out to music. The concerts didn’t happen this year, but it remains a place to stroll, relax and doze off to the sounds of rolling waves. Breathe in, out and repeat as many times as you need. For lunch, Gatsby on the Ocean serves up seafood with a side of views. The simple menu has dishes that rely more on flavor than frills, like the creamy and indulgent burrata. The lobster brioche roll, made with a citrus aioli and fries, is worth trying before, like the warm weather, it disappears.
Further East, villages like Bay Shore and Babylon are worth perusing. Babylon’s Lake Argyle is an easy walk, and Gardiner County Park is dog-friendly. End the day with dinner at LakeHouse. The intimate restaurant sits on real estate that’s prime for outdoor dining. Situated on a lake, as the name implies, it’s also home to a fire pit made for keeping guests toasty as the sun sets and temps dip. The caramelized local sea scallops, served with corn risotto and warm lemon-caper mint vinaigrette, taste a little sweet, a little citrusy and completely fresh. The S’More Sunday is as good as it sounds.
The Ocean Bay House is a fine spot to spend the night. Bay Shore’s waterfront inn rooms are bright and airy with nautical accents. You can see Fire Island from the appropriately named Fire Island room, and the East End room features a soaker tub made for relaxing weary muscles after a day of exploring.
Something With Wine
The North Fork wine trail has proven to be resilient in uncertain times, re-opening safely and successfully. And while it may not seem like there’s much to toast to this year, you’re surviving — and that’s worth raising a glass to.
From the Tuscan-style setting at Raphael’s to the more rustic spots like RG|NY and Macari, the North Fork offers a wide variety of atmospheres and vintages. Sparkling Pointe, the only vineyard on Long Island producing exclusively sparkling wine, is worth a stop for a festive tasting experience. The inside is light and airy and has a mantle decorated with award-winning bottles. Outside, there’s table service and views for days.
Mid-day, grab-and-go at Mattitaco. Vegetarians have options here. There’s the shrooms taco, made with grilled portobello and poblano peppers, and the farm-to-taco, made with crispy sweet potatoes and grilled sweet corn. The omnivores and carnivores may like the cheeseburger taco, which combines beef, provolone cheese and a pickled onion inside a flour tortilla.
Fall calls for hard cider, and Riverhead Ciderhouse and Woodside Orchards have it on tap. Wind down with a coveted seat at Noah’s. The tapas-focused spot makes dining an experience with sharable eats.
Something of a Great Escape
With its laidback, surfer vibe and pristine beaches, a trip to The End can feel like venturing to an entirely different world, rather than the tip of Suffolk County. Fall is the perfect time to enjoy it.
Begin with brunch at Tillie’s. One of the many dining options at Gurney’s Montauk Resort, the restaurant has an outdoor dining space. Indoors, its large windows give way to oceanfront views. Wellness fanatics will find a foodie home away from home at this spot. Dishes like the power bowl (house granola, Greek yogurt, chia seeds and macerated fruits ) and grains & greens (chermoula, poached eggs, quinoa, barley, Swiss chard mushrooms, sunflower seeds and charred bread) cater to the food-as-fuel crowd. There are also juices — the green goddess (pineapple, green apple, kale and ginger) tastes like a guilt-free dessert.
A trip to Montauk lighthouse is a must, if only for the Instagram photo. Venture down to the beach and savor what’s left of warm weather. Montauk Brewing Co. has emerged as one of the most recognizable breweries on the Island. Currently open for curbside pickup, call ahead and grab some cans to enjoy at home. The Wave Chaser IPA has tropical and pine aromas, and the Driftwood Ale is an easy-drinker with toasty, nutty and biscuit-y flavors.
Harvest on Fort Pond is a favorite dinner spot. The Tuscan-style restaurant serves some of the best Italian around, which is why it’s hard to get a table even in the off-season during normal times. Consider opting for a pizza — the bacon, onion, jalapeño, tomato and mozzarella is a daring choice. It goes perfectly with a bottle of red.
Staying over? Consider booking a room at Gurney’s — though the spa is currently closed, resort has all the other amenities you’d expect from a luxury hotel — or at Marram Montauk, a 96-room beachfront boutique hotel with a more low-key vibe and a location within walking distance to town.
Something Off-Island (Sort Of)
Like the Hamptons, Shelter Island is a destination. Unlike the Hamptons, it’s actually an island onto itself. A quick ferry ride from Sag Harbor or Greenport, the 8,000-acre island (population: 2,400) has lush, untouched green lands, blue skies and water and a small-town feel.
It’s worth staying a night on this Island, and Ram’s Head Inn is giving guests a chance to feel like they’ve not only escaped Long Island but gone to Europe. Each week, the Inn’s menu will feature flavors from countries, including Portugal (Sept. 24-29), Italy (Sept. 28-Oct. 4), Spain (Oct. 4-11), Brazil (Oct. 15-20) and Germany (Oct. 22-27). Accommodations are top-notch, making it a place locals and tourists alike return to year after year. Think tennis courts, a private beach, hammocks and access to water sports like kayaking and sailing.
It would be easy to stay put there, but it’s best to venture out. Mashomack Preserve, which at 2,000 acres takes up about one-third of the island, has a trail for anyone — some as short as 1.5 miles and one that’s 10 miles.