17 Memorial Day Weekend Getaways from NYC to Book ASAP

Stephanie Sengwe
·17 min read

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Memorial Day Weekend ushers in a few things: the ability to wear white jeans with abandon, the return of summer cookouts and the desire to flee the city as fast as humanly possible. Although the Jitneys are filling up fast, there’s still time to book a trip outside the boroughs for a quick refresh. From the charming towns of upstate New York to neighboring New Jersey, Connecticut and Pennsylvania, take your pick of these last-minute Memorial Day weekend getaways from NYC. Whether you choose the mountains or the beach, you’ll come back to the city ready to swing into summer.

Best Summer Weekend Getaways from NYC

1. Stockbridge, MA

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Catskills: Been there, road-tripped that. This year, go east of the Hudson to the Berkshires. Not only does it have the same cabin-and-trees situation, but it’s also rife with history. Norman Rockwell’s old studio is located here, featuring the largest collection of the artist’s work. Summer’s also a lovely time to visit the Berkshire Botanical Garden, which houses more than 3,000 species on 24 lush acres. Architecture buffs will enjoy an afternoon at Naumkeag, the 48-acre estate once belonging to the U.S. Ambassador to Great Britain, Joseph Choate. The “cottage” has 44 rooms, which you can tour in the summer, plus eight acres of formal gardens, in addition to meadows and farmland. After you’ve exhausted yourself, refreshment at the Rose Garden Cafe is essential (They also serve high tea on select weekends.)

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2. Old Saybrook, CT

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This little town on the shores of eastern Connecticut is basically one long Main Street—quaint New England at its finest. Stay at the Saybrook Point Resort & Marina for a home base that epitomizes old-world charm. (It’s also just a 20-minute walk to the beach.) Then, beeline for the Katharine Hepburn Cultural Arts Center, where you can catch a flick and walk through the museum, which displays memorabilia documenting the Hollywood legend’s life and career. Outdoor fans will appreciate time hiking through the coastal forest of The Preserve, a 1,700-acre enclave spanning Old Saybrook, Essex and Westbrook. And for the vintage enthusiasts, a stop at Essex Saybrook Antiques Village is essential. Here, 50-plus dealers hawk everything from furniture to antiques and jewelry in a 6,000-square-foot warehouse.

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3. Rehoboth Beach, DE

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If you’re looking to throw a big family bash, load up the RV and head over to Rehoboth Beach. The almost four-hour drive is the perfect amount of time to crank up some tunes and sing along without everyone losing their minds. And when you get there, everyone can tumble out directly into Funland, an amusement park where the kids can have a field day with carnival games and rides. Haul everyone to the boardwalk for more diverse entertainment. There’s a summer weekend concert series and no paucity of culinary delights—ice cream, baked goods, sweets, restaurants and taprooms abound. (Though if you had to choose, dip into Conch Island Key West Bar and Grill, a local institution with live music.) There’s a plethora of shops, too. From antiques to clothing, art, farmers markets and wineries, everyone will find something to enjoy.

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4. Cape May, NJ

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Looking for Memorial Day Weekend getaways from NYC right on the water? Say hello to Cape May, a beach town located at the southernmost tip of New Jersey. It’s filled to the brim with pastel-colored bed and breakfasts, antique shops, tennis courts and trolleys. You’ll want to check out the Emlen Physick Estate, an 18-room Victorian mansion designed by architect Frank Furness. A guided tour will show you characteristic Victorian Stick Style architecture and the way of life of the Physick family during the period. Afterwards, head over to Washington Street Mall, known as “the heart of Cape May.” Here, you’ll find Art Block Café, a coffee shop and art studio where you can sip boba, matcha and coffee while crafting. For some killer views, climb to the top of the Cape May lighthouse, which is still in operation. To get there, wind your way through the peaceful trails of Cape May Point State Park.

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5. Newport, RI

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Newport is just the destination for a Memorial Day Weekend getaway from NYC if you love The Gilded Age. Renowned for its mansions, the town is home to some incredibly sumptuous summer homes, including the legendary, Vanderbilt-owned Breakers. It holds the reputation as Newport’s most opulent “cottage”—if Italian Palazzo design, 50-foot ceilings, 70 rooms and 13 acres count as a cottage. Be sure to also visit the Marble House, built by William Vanderbilt as a 39th birthday present for his wife, Alva. Not an architecture fan? The Sailing Museum presents an enthralling dive into the sport. But if we’re being totally honest, we came for the oysters. (The Deck at Waite’s Wharf, Bar and Board Bistro and iconic The Black Pearl won’t steer you wrong.)

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6. Block Island, RI

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If you’re the type who likes to unplug on vacation (i.e., phoneless with zero chance of running into Erin from accounting at the Surf Lodge), this secluded isle off the coast of Rhode Island is just the ticket. Take the Amtrak to New London, Connecticut, where the train stops just steps from the Block Island Ferry dock, and you’re golden. Make your first stop the Block Island Historical Society, a quaint museum near New Shoreham exploring the region’s history. Here, you can learn about the region’s geological formation, Indigenous people and Victorian life. Another locale worth the stop is the North Lighthouse in New Shoreham. While you can’t climb to the top, you can visit the maritime museum on the first floor. And for those who truly want to unplug, book an appointment at the award-winning Koru Eco Spa—the signature sacred stone massage is a must.

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7. Shelter Island, NY

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  • Distance from NYC: 5 hours

  • Why We Recommend It: quiet getaway, boutique hotels, seafood

  • Where to Stay: Summer Paradise (from $300/night, sleeps 8); Island Boat Yard Home (from $561/night, sleeps 8); Casa Gypsea (from $390/night, sleeps 6)

OK, so forget Block Island—you’re dying to go out East. Try Shelter Island instead, in East Hampton just a hop and skip from Montauk. It’s quickly becoming its own hot summer destination. You’ll get the Long Island vibes you love, from sunbathing on Crescent Beach to hiking in Mashomack Nature Preserve. The outdoor-loving sporty people in your party will also appreciate kayaking to Taylors Island. (It’s only accessible by water—but renting a kayak is easy.) Be sure to check spend an hour or two at Havens’ House Museum, which explores the island’s history and sells books and goods by local artists and authors. And you’ll be needing a legendary milkshake at the Shelter Island Heights Pharmacy.

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8. Montauk, NY

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You just caught a ride to the Hamptons on Friday night. Score. Now, where to stay? For a true surf-inspired weekend, head to Marram. Chic quarters, beach cruisers and your choice of the waves or the pool. But don’t spend the entire weekend lounging. Adventure awaits. See the quintessential Montauk Point Lighthouse (and its museum) or take a hike at Amsterdam Beach State Park. (Note: The beach is rocky, and the hike is moderate.) If you want a unique experience, head to Deep Hollow Ranch, and they’ll lead you on a beach ride. Where food is concerned, you’re not in want of good eats. Duryea’s Lobster Deck slings seafood, Sel Rose makes a mean brunch and every local is throwing back a pint at Montauk Brewing Company.

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9. The Catskills, NY

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This may seem like an obvious choice, but the Catskills are popular for a reason. There is no shortage of things to do—from touring historic sites, to hiking Kaaterskill Falls, visiting local animal parks and even catching a theatre play. We recommend checking out the Hudson River Skywalk, a six-mile stretch that connects the Thomas Cole and Frederic Church national historic sites. At the former, you can visit the home and studios of the artist, environmentalist and founder of the Hudson River School of American landscape painting.

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10. Amagansett, NY

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When you visit Amagansett, take things up a notch (or three) at The Roundtree, where you can book your very own cottage complete with Frette linens, rainforest shower heads, continental room service breakfast and in-room massages. (And those are just some of the super-luxe perks available.) Once you’ve settled in, head out to Amber Waves Farm, Market and Cafe where you can indulge in fresh juice, pastries and a seasonal menu. Or grab everything to-go and picnic on Indian Wells Beach. (Though the destination has a slew of food trucks to choose from.) And should you want to spend the weekend partying, there’s no better place to do that than The Stephen Talkhouse, a local and mythical live music venue that’s hosted local acts and international performers alike.

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11. Mystic, CT

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  • Distance from NYC: 5 hours

  • Why We Recommend It: small town charm, quiet, family-friendly

  • Where to Stay: The Mooring House (from $700/night, sleeps 8); Mystic Hideaway (from $178/night, sleeps 6); SeaWolf House (from $179/night, sleeps 4)

Historic Mystic is the ultimate antithesis to New York City. This little town is always bustling with tourists but is not nearly as overcrowded as the Big Apple. Known for its maritime culture, there are plenty of water-based activities for the family to partake in, from kayaking to power boating. Those who prefer to stay on solid ground can have a blast at the Mystic Seaport Museum—the nation’s leading maritime museum—or head to the Mystic Aquarium for some quality time with the whales. And if water really isn’t your jive, then a stroll through the charming Old Mistick Village will be. Stock up on peculiar books at Alice’s Haunted Little Bookshop, channel your inner kid and pick up a kit at Mystic Kite Shop and finish the day at Mango’s Wood Fired Pizza Co.

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12. Tarrytown, NY

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  • Distance from NYC: 1 hour and 15 minutes

  • Why We Recommend It: quaint village, short trip, boutique shopping

  • Where to Stay: Tarrytown Studio (from $200/night, sleeps 4); Charming Victorian Home (from $373/night, sleeps 9); Modern Duplex (from $286/night, sleeps 10)

Maybe you don’t want to go too far away from the city; you just want to escape the Memorial Day madness. Head over to Tarrytown, which is only an hour and 15 minutes away. Merely 25 miles north of Midtown Manhattan, this village is also served by a stop on the Metro-North Hudson line, so you don’t have to worry about traffic. Once you touch down, you can spend the day shopping at the various local boutiques, like the cabinet of curiosities, Bella’s Boutique. Bookworms will want to steep themselves in the literary history by paying a visit to Washington Irving’s home, Sunnyside. You can also tour the beautiful grounds at the Gothic-revival Lyndhurst mansion. Both properties are exemplary pillars of 19th and 20th century architecture. Top it off with a nice dinner at popular eateries such as Sweet Grass Grill or Bistro 12.

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13. Nantucket, MA

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It may not be officially summer yet, but the beautiful beaches, towering lighthouses and dreamlike harbors of Nantucket will have you rocking your short shorts and T-shirts in no time. Check out larger than life exhibitions at the renowned Whaling Museum, take a load off at Madaket Beach (or Jetties or Surfside) or go for a hearty lunch offset by some booze courtesy of Cisco Brewers. Hey, you’re on vacation, right?

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14. Saranac Lake, NY

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If you’re looking for a quiet Memorial Day Weekend getaway that allows you to disconnect and become one with nature, then Saranac Lake is the ideal destination. Nestled in the Adirondack Mountains, this small village was once used as a hideaway by the likes of Mark Twain and Robert Louis Stevenson. Saranac Lake offers you the opportunity to detach from the outside world and truly unwind. Our recommended itinerary consists of coffee shop hopping (Blue Moon Cafe, Nori’s Village Market and Origin Coffee Co. are great places to start) and a romantic stroll along the eponymous lake. You can also hike Baker Mountain or go river walking. Don't leave town without checking out the local arts scene, which includes the Adirondack’s only year-round professional theater, Pendragon Theatre, and art galleries galore.

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15. The Poconos, PA

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  • Distance from NYC: 2 hours and 30 minutes

  • Why We Recommend It: charming small-town ambience, outdoor activities for all ages, affordable

  • Where to Stay: Lakefront Pocono House (from $375/night, sleeps 10); The Hummingbird Cabin (from $288/night, sleeps 6); Saw Creek Estate (from $186/night, sleeps 9)

The Poconos mountains are an ideal Memorial Day Weekend getaway, offering a host of outdoor activities that allow you to take advantage of that gloriously warm, pre-summer weather. Plus, it’s less than a three-hour drive from the city. The charming small-town vibe provides a beautiful backdrop for hiking, whitewater rafting, suntanning on one of the many beaches and taking a scenic historic trolley tour of the region. Foodies will appreciate pit stops at Hanna’s Farm Market, a family-owned roadside stand with locally-sourced food and produce. Additionally, the Poconos is home to Moka Origins Roastery and Chocolate Factory, which is a siren song to chocoholics and caffeine addicts. Don’t leave the area without touring the Castle Inn at the Delaware Water Gap. A guided tour will take you through the building's interesting history as a Victorian resort, boxers’ training ground and music headquarters under Big Band leader Fred Waring.

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16. Rockaway Beach, NY

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  • Distance from NYC: 1 hour

  • Why We Recommend It: accessible by subway, can go in for the day, free beach access

  • Where to Stay: The Rockaway Hotel (from $357/night); Five Towns Inn (from $356/night); Seaside Nest (from $199/night, sleeps 3)

If you’re searching for Memorial Day Weekend getaways from NYC but don’t want to pay holiday weekend pricing, we suggest Rockaway Beach in Queens. It’s a popular summer spot accessible by subway, so you can easily come in for the day. Plus, beach access is free. Before setting up camp and staking your beach umbrella in the sand, grab a box of danishes and sandwiches from Rockaway Beach Bakery. When you arrive at the beach, there are several entrances: 67th street has the best waves, while 90th to 98th streets are lined with restaurants. (Rippers, a seasonal, open-air bar with live music, is a must.) Those with kiddos or lots of gear are best off entering at 105th to 116th streets, a calmer stretch with a paid parking lot by 116th. Wrap your beach day by checking out the local shops—jewelry, caftans and coverups at Swellife and vintage books, clothing and more at Zingara.

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17. North Fork, NY

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  • Distance from NYC: 2 hours and 15 minutes

  • Why We Recommend It: lots of charming towns with a booming local culinary scene

  • Where to Stay: Greenporter Hotel (from $240/night); Menhaden Hotel (from $739/night); Wine Country Home (from $331/night, sleeps 8)

On the outer reaches of Long Island is the charming peninsula of North Fork, populated by bucolic wineries and waterside villages. For the food, wine and art connoisseurs, this is one of the ultimate Memorial Day Weekend getaways from NYC. A perfect day trip includes coffee at the beloved, local-owned Aldo’s Coffee Company, and a slice of focaccia at Salumeria Sarto. You’ll want to bring or rent bicycles and take the 10-mile (round-trip) ride from Greenport to Latham Farmstand, loading up on local produce, florals and seaside village views. Poppy & Rose boutique winery is also a must, as well as a meal at Anker. The Greenport institution serves a monthly rotating menu using locally sourced ingredients. While away the afternoon at North Fork Arts Center (located in the historic Greenport Theater) and stroll the docks. At nightfall, you can head to Long Island’s oldest public observatory, Custer Institute and Observatory, to see if you can spy the Big Dipper.

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