15 Memorial Day Weekend Getaways from NYC to Book ASAP

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Memorial Day Weekend ushers in a few things: the ability to wear white jeans with abandon, those little gems we like to call Summer Fridays 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

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1. Stockbridge, MA

Catskills: Been there, road-tripped that. This year, go east of the Hudson to the Berkshires. Not only does it have the same (obvious) cabin-and-trees situation, but it’s also rife with history. (Psst: Norman Rockwell’s old studio is located here.) The centrally located Red Lion Inn is a fan favorite, we suggest you hop to it.

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2. Old Saybrook, CT

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).

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3. Rehoboth Beach, DE

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. You can stay in lush rentals such as this gorgeous beach villa that sleeps 15 people comfortably. It comes with a ping pong table and board games perfect for a rowdy family game night.

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4. Cape May, NJ

Looking for something right on the water? Check into the La Mer Beachfront Resort in this pretty-as-a-postcard beach town. Located at the southernmost tip of New Jersey, Cape May is filled to the brim with pastel-colored bed and breakfasts, antique shops, tennis courts and trolleys. Just think of the Instagram stories!

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5. Newport, RI

A modern hotel in the heart of historic Newport, The Newport Harbor Hotel & Marina is primed for a fantastic weekend escape. Um, have you seen the Marina-dining situation? What about the indoor heated saltwater pool? Take advantage of your Zipcar membership and scoot on up there first thing Friday morning for a real long weekend without too much traffic (fingers crossed).

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6. Block Island, RI

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.

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7. Shelter Island, NY

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, 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. If you need us, we’ll be lounging in the hammock.

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8. Montauk, NY

You just caught a ride to the Hamptons on Friday night. Score. Now, where to stay? For a true surf-inspired weekend, head to the Marram. Chic quarters, beach cruisers and your choice of the waves or the pool. For some adventure, visit the Montauk Brewing Company, Montauk Point State Park or Deep Hollow Ranch.

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9. The Catskills, NY

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, visiting local animal parks and even catching a theatre play, your stay in the Catskills will be eventful.

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10. Amagansett, NY

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.)

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11. Mystic, CT

  • Distance from NYC: 5 hours
  • Why We Recommend It: small town charm, quiet, family-friendly
  • Where to Stay: The Mooring House (from $500/night, sleeps 8); Mystic Hideaway (from $195/night, sleeps 6); SeaWolf House (from $220/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.

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12. Tarrytown, NY

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 the various local boutiques, tour the beautiful grounds at Lyndhurst mansion and 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

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 off set by some booze courtesy of Cisco Brewers. Hey, you’re on vacation, right?

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14. Saranac Lake, NY

If you’re looking for a quiet 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. Whether you take a romantic stroll along the eponymous lake, hike on Baker Mountain or go river walking, you’ll definitely feel like you’re in your own little world.

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15. The Poconos, PA

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, a day at the waterpark, suntanning on one of the many beaches and taking a scenic train tour of the region.

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