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5 Best Day Trips from New York City

Where to go when you need a break from the city that never sleeps.
Tourists North Adams

New York City has endless allure for residents and visitors, from its cultural attractions to its dining and nightlife scene, but sometimes what you need most from New York is a break. Seated where it is on the northeast corridor, there are plenty of great escapes you can tackle in a day or long weekend. These places that are just a train or car ride away from NYC combine ease of access with a fresh vibe no less full of appeal: from the nearby waterfront to the charming towns upstate. These are the best day trips from NYC.

Click the link to read our complete New York City guide.

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  • CityGuidesDayTripsPlaceholder1

    HUDSON VALLEY, NEW YORK

    A short jaunt on the Metro North from New York City, these two little towns have become popular in spring, summer, and fall. They're beautiful, with DIA: Beacon the star around which a constellation of eating, drinking, and hotel options have sprung up. Since they're a quick car or train ride apart, you could see both in one day, if you like. Consider steak frites, ice cream by the water, drinks overlooking a rumbling waterfall, and a quaint B&B if you can't bear to leave so quickly.

  • Courtesy The Roundhouse
    restaurant

    The Patio Grill at The RoundhouseArrow

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    This former dye mill (now hotel) overlooks Beacon Falls, and boy are they gorgeous, particularly in the spring, summer, and fall from the seasonally open Patio Grill. (Mother Nature did good work on both the lighting and the water feature.) The menu changes all the time, and past hits have included a burger with smoked Gouda, fried shrimp with spicy mayo, and a pretty solid salad. Keep it simple and go for wine or beer on tap; cocktails are ambitious but don’t always hit the mark. This food isn’t going to blow your mind, nor will it break the bank: You’re here for that view.

  • Meghan Spiro
    bar

    DogwoodArrow

    $

    One of a couple neighborhood bars where you can really feel the chill Beacon vibe, this one is studded with locals hunkered in their booths, or tipping back a few local on-tap drafts. You’ve got 16 taps on draft, solid cocktails but nothing fancy, and wine from California, France, and Italy, for the most part (We’d go with a pint). You're wanting a burger, some wings, jumbo stuffed tater tots, a pint, and some gossip. This place has all of it.

  • Courtesy Bannerman Island
    activity

    Hudson River ExpeditionsArrow

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    This rustic kayak tour takes you to the still-beautiful Bannerman Castle, which is in a state of photogenic dishabille. Guides tend to be on the very friendly side, and the folks hosting you at the castle itself are bookish and know their stuff. This late spring to early fall operation is pretty much right on the Hudson, which is perhaps why the folks running the show seem to understand the river itself. You’ll want to book in advance, but if you’re in the neighborhood, feel free to pop by just in case there are openings. They have a Peekskill, NY location, too.

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    Cold Spring Antiques CenterArrow

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    Tiny, cluttered, and wonderful, this is one of a clutch of great antiques and vintage shops peppering Main Street. Mix-and-match bakelite flatware (a steal) is packed in right alongside vintage Mister Rogers albums, and a lamp of a white monkey clutching a lightbulb. It’s a hoarder’s fever dream. Remember that half the pleasure of vintage and antique shopping is in The Dig. Spend some time shuffling through old photos, posters and the like, and you might just find a diamond in the rough. (But probably not an actual diamond.)

  • Courtesy Storm King Art Center
    activity

    Storm King Art CenterArrow

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    Forget what you think you know about tiny, manicured sculpture gardens. Storm King Art Center—simply, Storm King to those fleeing the city to see it—is an extraordinary 500-acre outdoor museum, complete with works from Alexander Calder, Zhang Huan, and Sol LeWitt. In autumn, it’s hard to say what’s more striking here: the artwork or the scenery. Strap on your best walking shoes and pack a picnic. You’ll want to spend a day exploring here.

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    BackbarArrow

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    Is this a bar? A vintage shop? A restaurant? Backbar looks a bit like all three. But, at its core, it’s a bar with food worth getting in a car for. Zak Pelaccio, who once operated Fatty Crab in Manhattan, and later decamped to the Hudson Valley, is behind the project. It's geared towards locals but will allow those visiting for the weekend to join in. Pull up a seat at the bar or in the large outside space if the weather’s nice. With a name like Backbar, it’s fair to expect high level drinks. That expectation is certainly met with simple but well executed cocktails like the bee’s knees with citadelle gin, honey, and lemon, and slushies like the Lucy, made with tequila, fresh lime juice, and topped with Prosecco. There’s also a board for local beer offerings and cocktail specials. If you're in the Upper Hudson Valley, you really shouldn't miss Backbar, regardless of whether you're with your partner, parents, or friends.

  • Brandon Pidala
    hotel

    Pig Hill InnArrow

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    This 1825-era B&B is adorable, right on Main Street, and comes with a fabulous breakfast. Rooms have four-poster beds, canopies, and lacy coverlets—all the details are spot-on, right down to the clawfoot tubs. There's a cute little "conservatory" for dining with other guests after a night of sleep, and you can sip wine in front of a wood-burning fire. Of all the older options downtown, this is the best by a longshot.

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    BrunetteArrow

    New to natural wine? The staff here is happy to help guide you. Don’t be shy, just ask. The wine offerings change daily, but expect at least 10 or so wines to be available by the glass like an orange chardonnay from Marche, Italy, and a sparkling red. There are also beers including those from Hudson Valley’s Suarez Family Brewery. Just like the wine offerings, the team says the food menu can change with abandon and without notice, but that’s part of the fun. You might find hot dogs with pickled carrots, shrimp cocktail, and burrata with fennel. Don’t skip the trout roe nachos.

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    Moo Moo's CreameryArrow

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    Small and quaint, with all the hallmarks you’ve come to expect of an ice cream shop—barely legible signs denoting ice cream flavors scrawled in every color, cute black-and-white tiled floors, teenage scoopers whose moods vary by the day—this is a great place for a to-go cone. Even New England ice cream snobs should be able to get behind the relatively creamy texture and straightforward flavors proffered here. (Think: coffee chip and chocolate Oreo.) The fanciest, Mexican chocolate, is good and punchy with the requisite cinnamon. The mouthfeel is what matters—buttery, luxe, and creamy, not icy—and Moo Moo’s usually nails it.

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  • GREENPORT, LONG ISLAND

    Keep driving East and North from New York City. Let the last Burger King and Friendly's drop off in the rearview mirror. Observe as apple orchards, breweries, cows and Canadian geese pop into view. Marvel at how the vineyards seem to stretch right to the horizon. You're in the North Fork, baby. Shuck some oysters, hit the beach, have some wine, and most importantly, slow your roll.

  • Estafany Molina
    restaurant

    Aldo'sArrow

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    Locals have been coming to this cozy café since it opened in 1987 to sip espresso drinks and chat over the day's news. It's such a neighborhood institution, even Starbucks closed after four years when it opened across the street. The coffee runs strong and we’d recommend it in latte or mocha form, to balance its intensity. Chocolate-dipped biscotti—which you can buy to go—croissants, and scones are the things to snack with your drink.

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    Little Creek Oyster Farm & MarketArrow

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    This nautical oyster hideout by the docks is tiny, popular, and fun, known for its slogan, “Shuck Your Self.” New Englanders and anyone else who grew up shucking their own oysters will delight that it’s half-price here ($20 versus $36 for a pre-shucked dozen) if you do so. If you don’t know where to start, someone will teach you. Oysters here are divine, since this restaurant is part of a local collective working with dozens of individual farmers and harvesters. If you’re here from The City, the wine prices by the bottle might make you a little weak-kneed. Pull yourself together and order a classic oyster pairing: Muscadet, Champagne, or—yes, it works—chocolatey Oyster Stout from Greenport Brewing.

  • Caroline Rocchetta
    restaurant

    1943 Pizza BarArrow

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    Intimate and simple, with burnt-orange walls and a wood-fired brick oven, crowds come to clamor over the attractive pizzas they're slinging. Even Ina Garten is a fan of these 14-inch thin-crust pies, with their prettily bubbled crusts. The options vary: You could do a margherita simply dressed with mozzarella, tomato sauce, and basil, or you could order the innovative clams casino (fresh clams, bacon, green peppers, and garlic on a white pie). This place can be a nice change from the hustling, bustling pizzerias of Manhattan.

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    Croteaux VineyardsArrow

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    This is off the beaten path of the vineyards lining the North Fork, and it makes for a nice change of pace, with a wonderful garden and tasting barn, and delicious rosé. Everyone’s got a glass of rosé or bubbly rosé, and most folks will order a flight—they’re cheap by Manhattan standards. We love the selection of rosé sparklers, of which you can order a trio at a time, including the deep, juicy Cabernet Franc sparkler (if they have it). Do know that the bar is a warm-weather operation and will reopen before April.

  • Courtesy White Flower Farmhouse
    shop

    White Flower FarmhouseArrow

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    Farmhouse antiques are the specialties at this downtown Southold shop—as far as the eye can see—with home decor, kitchenware, and other finds in the mix. Maybe you need a mirror framed in distressed wood? An antique table? Hand-thrown ceramics or a few yard sale items just purchased in the French countryside? These are the vintage and “vintage-inspired” housewares and linens you dream about. If you're a New Yorker trying like hell to make your Brooklyn home into a tiny little country cottage, this is your place.  We’re not gonna say we’d fight you for the matched sets of Bakelite flatware or the cool blue-and-red vintage sailboat rental signs, but…

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  • Caroline Rochetta
    bar

    Brix & RyeArrow

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    Cocktail obsessives have one daydream: to find a bar with excellent drinks for about a third of what they’d pay in New York or San Francisco. This is that bar. Order The Last Word if you’ve never had one, a Sazerac, or maybe something made with sherry, a fortified wine that drinks master Evan Bucholz understands how to wield wisely. Use those cocktails to wash down pizza from 1943 Pizza Bar next door. Whether you go for a white pie decked out with clams or a classic margherita, the food here—including some killer wood-fired meatballs—is better than most people expect.

  • Courtesy American Beech Hotel 
    hotel

    American Beech HotelArrow

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    The design at American Beech fits somewhere between LA, Miami Beach, and Greenport. There are whitewashed suites, an Instagrammable bar, and large plants outside. Somehow, the three styles all come together to make one of the chicest places on the North Fork. There are only 11 rooms at this boutique hotel, so book in advance during peak season. Note that some are located over the bustling restaurant, so if you’re looking for peace and quiet, opt for one of the other rooms located around Stirling Square. This spot is as much about the restaurant and bar as it is the hotel. The roomy restaurant, which is closed during the winter, can accommodate large parties, so if you’re visiting the North Fork for, say, a bachelorette, this is a great choice. The menu hops around from cumin-cured duck wings to spaghetti squash latkes and a smash burger with cheddar. 

    Book Now at Expedia
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    Eagle's Neck PaddlingArrow

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    The employees of this kayak outfitter are locals, and they want you to relax—Orient Beach State Park is a national landmark, thanks to its unusual maritime forest and its plethora of great blue herons, egrets, ospreys, and crowned night herons. Guides can point out beautiful vistas, but you could also do that on your own. (Costs are similar whether you take the tour or not.) Outdoorsy types will love seeing how far they can get in two hours, and the lazy dabblers among us will enjoy just how chill kayaking can be.

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    activity

    North Ferry CompanyArrow

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    This is a daily ferry leaving every 10, 20 or 30 minutes to take you to Shelter Island. You came all the way to Greenport. You want to see more of the water. For $2 each way, this is how you do it. This is the best way to get some beach time in—and truly escape the city—without paying much. Rent or bring a bike; the island is totally easy to get around on one. Then go to the beach with a bottle of something delicious.

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  • NORTH ADAMS, MASSACHUSETTS

    Mass MoCA is a behemoth hub of the arts for many miles in every direction, playing host to artists as varied and marvelous as David Byrne, Wilco, Xu Bing, and Katharina Grosse. It's definitely a can't-miss, but as you drive here, marveling at the rolling hills and sprawling natural beauty, you'll want to know where to eat and sleep, too. One of our favorite boutique hotels is here, featuring a hot tub where you can sip bourbon under the stars, after a day at the museum. A trip to this part of the world is like hitting a reset button.

  • Zoran Orli
    activity

    MASS MoCAArrow

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    This sprawling museum lures history buffs and art fans alike. The 16-acre complex of 19th-century mill buildings occupies almost a third of the North Adams downtown business region. It is a mind-bending museum. James Turrell, Xu Bing, and Katharina Grosse are among the artists who revel in just how much space is here. The curation is smart, using the gargantuan ceilings and old trappings of the place to make you feel dwarfed, but not diminished. When you need a break, there is a brewpub here, a good café, ice cream, and a fine dining restaurant.

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  • © Yakoniva / Alamy
    hotel

    The Porches Inn at MASS MoCAArrow

    $ | Readers' Choice Awards 2023

    A string of 19th century Victorian row houses, lined by porches with slightly ominous identical rocking chairs. This place is dwarfed by Mass MoCA just across the street, but you notice the hotel owner’s attention to detail as soon as you park and see the lobby. The tub in your room will be so gorgeous you’ll want to pull it from the floorboards and take it home. And if you miss out on the hot tub, at night, under the stars and foliage, with a bourbon, neat, in your hand (they’re fine with that at the front desk), you are not doing it right. So long as you're not a diva needing to count threads in the sheets, Porches' style and attention to detail may just ruin you for other boutique hotels.

    Book Now at Expedia
  • Jonathan Welch / Alamy Stock Photo
    activity

    Cascade WaterfallArrow

    At the end of this hike is a picturesque, cold waterfall. The air is crisp and clean here, and it feels a bit like you fell off the map, in the best way. Relatively easy for beginning hikers, sometimes with a bit of mud at the end of the trail, this is a slightly tricky-to-find spot with unfortunately few easements. But if you don't mind muddying your boots a bit, and just want to stretch your legs without going all out, this one's for you.

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    Pedrin's Dairy BarArrow

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    The words on the awning say it all: “Pedrin’s Dairy Bar: Home of the Fish Fry.” Brace for MASS MoCA tourists and locals wishing they lived a little closer to the beach, all happily digging into sundaes and deeply fried fish ‘n chips. This is a quick fix for a few New England greats, all to be spread out over a white or red picnic table and—as they say—housed. Fried fish, clam strips, cheap burgers, and bountiful ice cream: This isn’t a place you walk away from feeling light on your feet, but some of us like to get all our indulgences in at one go.

  • Jessica Smolinski
    activity

    Williams College Museum of ArtArrow

    Dedicated art lovers know that there’s more to see in this corner of the Berkshires than the large-scale installations at MASS MoCA. Just down the road sits William College Museum of Art, or WCMA, a small but mighty museum that’s home to 15,000 pieces that range from ancient Egyptian and Assyrian to works from living American artists. The collection here has a bit of everything. There are outdoor sculptures, an archive dedicated to brothers Maurice and Charles Prendergast, and pieces from contemporary artists. Students at Williams College are lucky enough to be able to loan select pieces from the collection for a semester.

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    TouristsArrow

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    Inspired by the American roadside motor lodge of yore, Tourists is built for contemporary design lovers with lots of light wood on the banks of the Hoosic River. Many of the large windows in guest rooms look straight into nature, helping blur the line between the outdoors and indoors. Opened in 2018, Tourists still feels like the cool new kid on the block with the clientele to match. For those exploring Williamstown and North Adams, Tourists is perfectly situated. It’s approximately three miles from the Clark Art Institute, MASS MoCA, and Bright Ideas Brewing. If you’re visiting this corner of the Berkshires, there’s nowhere more stylish to stay.

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    The Distillery at Greylock WORKSArrow

    The historic Greylock Works mill has been converted into a stylish home for this distillery from Colorado that relocated to the Berkshires and opened here in 2019. Inside the distilling room sits a 20 person bar that makes drinks exclusively from housemade liquors and is open on Friday and Saturday evenings—perfect for folks visiting from out of town. Take a bottle for your friends back home and know that for each bottle you buy, you’ll get a complimentary cocktail or flight.

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  • PHILADELPHIA, PENNSYLVANIA

    The City of Brotherly Love has been luring lovers of art and dining from NYC and Washington, D.C., in recent years, and can compete on the national level on both fronts. With arguably the best Israeli cuisine in America, a trio of knockout museums, and even a Four Seasons, it's a destination town. Here's where to sleep, drink, eat, and play in Philly right now.

  • Alexandra Hawkins
    restaurant

    ZahavArrow

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    When James Beard Award-winning chef Michael Solomonov opened Zahav over a decade ago, it was one of only a handful of Israeli restaurants in the U.S. that served dishes other than hummus and shakshuka. Since then, upscale Israeli restaurants have sprouted in major cities across the country, and Americans have learned how to say "tehina." But despite the competition it's created, Zahav remains one of the best (if not the very best). Every meal here should start with Solomonov's silken hummus and laffa, a just-barely singed Iraqi flat bread, and salatim, a selection of Israeli salads and dips you can plunge that laffa into. From there, there's no wrong turn: Choose plates like chicken shishlik with plum, fennel, and sumac, or black sea bass tartare with bulgur and preserved orange. And save room for the restaurant’s iconic pomegranate-glazed lamb shoulder.

    If you can’t score a table at Zahav, try Laser Wolf, which serves several salatim (Middle Eastern salads) and skewers like Yemenite beef kebabs and mushroom shishlik, which are kissed with charcoal.

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  • Alamy
    shop

    Reading Terminal MarketArrow

    All of humanity seems to have come together in a happy hubbub at Reading Terminal Market. The sprawling space has been around since 1893, though now, its vegetable, fish, and meat vendors are compounded by dozens of restaurants, bakeries, and bars. Look for old-timey neon signs to help you make sense of the dozens of options—or just head straight for DiNic's, where the roast pork sandwich, topped with a frenzy of broccoli rabe, is practically the beating heart of the place. Follow it up with a scoop (or three) of Bassett's silky ice cream.

  • Courtesy Philadelphia Museum of Art
    activity

    Philadelphia Museum of ArtArrow

    Classic, grand, and impressive, the Philadelphia Museum of Art is a cultural institution. It is Philadelphia's answer to the Louvre, and houses one of the country's finest collections of art and sculpture. Tourists, locals, the stroller set…the gang's all here and they're all taking in the art at their own pace. Some skip entire galleries based on interests, while others read every placard. It's a choose your own adventure kind of place. And if all of this culture makes you hungry, you're in luck. The Cafe is bright and welcoming and features a variety of tasty sandwiches, soups, pizzas, and more. Prefer to cool your heels in a more formal setting? The Stir is an elegant spot designed by Frank Gehry that's perfect for lingering and lunching.

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  • Courtesy Briar Vintage 
    shop

    Briar VintageArrow

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    Vintage for gentlemen! This extraordinary place is one of a bevy of great vintage shops sprinkled around Philly, though it has some of the best men’s gear. Silk ascots, waistcoats, bowties, jackets, and an attentive owner who knows your size on site? It’s like stepping into a Gary Cooper vehicle. Don't leave without a smart vintage watch and, if you're feeling especially adventurous, a full tuxedo with tails.

  • Courtesy Four Seasons
    hotel

    Four Seasons Hotel Philadelphia at Comcast CenterArrow

    $$$ | Readers' Choice Awards 2020, 2021, 2022, 2023

    This is a Four Seasons, so you can expect seamless service and a lot of greige carpeting. However, this particular outpost is somewhat unique in that so many big names were tapped for its creation: floral designer Jeff Leatham, composer Brian Eno, architect Norman Foster, and chefs Jean-Georges Vongerichten and Greg Vernick. Their contributions along with expansive skyline views from every vantage point on the property and passionate, genuine service could make this the beginning of a transformation of Philadelphia's hotel scene. 

    Book Now at Expedia
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  • Courtesy La Colombe
    bar

    La ColombeArrow

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    La Colombe’s Fishtown location is unlike any of its many other outposts. The sprawling space is home to a roastery, a coffee laboratory, an open kitchen, a shop, and lots of seating. To call it a coffee shop would be to miss the point. There are fresh baked goods and other cafe standards aplenty here, but you’re really here for the coffee like pour overs, nitro lattes, and of course all of the espresso standards perfectly prepared. For coffee nerds or those with coffee lovers at home, there’s also a shop where you can pick up bags of La Colombe’s coffee to take home. Curious diners should consider stopping in for coffee and heading over to nearby Suraya for a Lebanese brunch.

  • Courtesy Cadence  
    restaurant

    CadenceArrow

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    Food & Wine named this South Kensington restaurant the best new one in the U.S. in 2019. Note though, you're not here for the aesthetics; you’re here for the food. The $68 four-course prix-fixe menu offers a handful of choices of thoughtful and creative dishes for each course. In the winter, you might find wagyu beef tartar with smoked cheddar, herb dumplings with seafood ragu, or n’duja stuffed quail. Each course also contains a vegan dish, or one that could easily be prepared that way. If both you and your date enjoy meat, call ahead to see if the Keiser duck for two with mushrooms, sunchoke, sichuan, and sunflower will be available that evening. While BYOB, Cadence does have seasonal vinegar sodas, kombucha, and mate from Pennsylvania producers on offer. It strikes that rare balance of special and creative but still welcoming and comfortable. The space is cozy, so bring a date or a small gathering of food-loving friends.

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  • Jillian Guyette
    restaurant

    Jim's South StreetArrow

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    Most cheesesteak shops in Philadelphia focus so closely on the rolls, onions, steak, and wiz, not to mention claiming the title of the best cheesesteak in the city, that a comfortable place in which to eat the sandwich is often overlooked. The team at Jim’s, which has been making cheesesteaks in Philly for almost 80 years, thankfully doesn't fall into that camp. Located on the corner of Fourth and South Streets, you can typically spot Jim’s before you arrive from the line snaking outside, down Fourth Street towards tattoo shops and piercing parlors. Once you’re inside, split up your team. While one person waits in line to place orders for cheesesteaks "wit whiz" (Cheese Whiz, that is), provolone, or American, or an Italian hoagie, the rest of the crew can head upstairs to stake out a table. It’s a bit of a production, but well worth it for a cheesesteak that never disappoints—and a place that lets you enjoy.

  • Getty
    activity

    Independence National Historic ParkArrow

    Philadelphia is the only UNESCO World Heritage City in the United States precisely because of the historical events that transpired right here, and it’s not just one museum or historic landmark. Rather, it’s a collection of buildings that played host to events that shaped American independence or honor that hard-won heritage. Begin at the Visitor Center to get your bearings and start your tour—visitors can enter with timed entry tickets—at Independence Hall, then stop by the Liberty Bell Center for a look at ostensibly the most famous broken item in the world. Afterwards, wander past the park’s other historic buildings including Carpenters Hall, the meeting site of the first Continental Congress, then make your way to the Benjamin Franklin Museum. Just note the airport-style security (and subsequent foot traffic) you're bound to encounter, and make sure you wear comfortable shoes—you'll be doing a lot of walking.

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  • THE HAMPTONS, NEW YORK

    It's famous on so many fronts: as a tony playground for celebrities and the Manhattan elite, but also for its earthier roots—lush farms, beaches, and quaint villages. Do as the locals do, and hit the bakeries, sandwich spots, farm stands, and under-the-radar museums and galleries that really make it stand out. Then, you'll understand why the crowds beeline for it as soon as the weekend hits.

  • Satin Sky
    restaurant

    Carissa's The BakeryArrow

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    The most Williamsburg-ified place in the Hamptons, Carissa’s started as a tiny walk-in-closet-sized space but has graduated and expanded to a second, larger two-building space on Pantigo Road. At the new location, the house is still stocked with artful pastries that would impress at that dinner party your Hamptons host is throwing. But, there’s also a more fleshed out café menu and dinner offerings like fried Montauk monkfish and spaghetti al limone. You can (and should) still load up sourdough and pie though.

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  • Courtesy Breadzilla 
    restaurant

    BreadzillaArrow

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    This unfussy family-run bakery churns out the best loaves of bread, sandwiches, and pastries on the East End of Long Island. It draws a mix of locals and "summer people," lots of families stocking up on sandwiches for the beach, people buying loaves of cinnamon brioche and seven grain boules for their houseguests. The lobster roll, served on a pillowy soft round of brioche, is superb, but so are most of the turkey-and-cheddar kinds of classics (this isn't haute cuisine, but it's exactly what you want for a beach picnic).

  • Getty
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    Pollock-Krasner HouseArrow

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    This 19th-century shingle-style farmhouse in the Springs was home to the abstract expressionist painter Jackson Pollock and his wife, Lee Krasner, until the late '80s. It's been left pretty much intact: the shelves are filled with books, Krasner's necklaces still hang on hooks in the bedroom, and, most fascinatingly, the drips from Pollock's most famous paintings still cover the wooden floor in his studio. It's a seasonal site, open May through October.

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  • Courtesy Round Swamp Farm 
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    Round Swamp FarmArrow

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    The Hamptons are filled with "farm stands" that are really specialty food boutiques. This is one of them, and it's the absolute best. Fresh peaches, white corn, and blackberries from local farms, eggs from the neighboring Iacono chicken coop, and tasty prepared salads and pasta, but the real draw are the baked goods: lemon pound cake, mini chocolate chip cookies, and crumble-topped pies oozing with fruit. There aren't any prices on anything. You'll wince when they start ringing you up at the register, but the baked goods and fresh produce are as good as the people-watching.

  • Courtesy Hampton Chutney Co.
    restaurant

    Hampton Chutney Co.Arrow

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    A counter service Indian-ish café, it's known for its massive, delicious dosas served on big plastic lunch trays and filled with grilled curried chicken, jack cheese, fresh veggies and plenty of avocado. Skip the sandwiches. You're here for the crispy, light-as-air, longer-than-your-arm dosas that you'll think are too big for one person to finish alone (you'll be wrong). One bite and you'll wonder why every order isn't served on this crepe-like wonder. The breakfast dosa is a Sunday morning home run, and the curry chutney chicken is like a chicken salad sandwich that just came back from a semester abroad in New Delhi. Everything comes with your choice of chutney for dipping and spreading—they're all tasty, but you can't go wrong with the herby cilantro.

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    Bridgehampton Candy KitchenArrow

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    On-the-nose classic 1950's luncheonette. There's a striped awning and neon lettering out front, leather-covered stools at the counter, booths lining the wall, paper menus-slash-placemats. They're known for their homemade ice cream: the flavors are listed on a board above the counter, where waitresses have been blending milkshakes in old-school machines for years, and there's a case where you can buy gallon containers of the stuff by the door. Stick to the classics and don't pass up a milkshake or malt.

  • Eric Striffler
    restaurant

    La FonditaArrow

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    It's a seasonally-open taco shack (albeit one brought to you by the restaurateurs behind the chic Nick and Toni's) off the highway in Amagansett, with reggaeton on the stereo, technicolor picnic tables on the grass outside, and guacamole served in little plastic tubs. There's a full menu of tortas, burrito bowls, salads, and tostadas, but tacos are the way to go. Get some chips and guac to start, then a few Baja-style fish tacos, chicken tingas, and al pastors. Wash it down with Jarritos or a Modelo.

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  • Alamy
    activity

    Hither Hills State ParkArrow

    Hither Hills is a network of trails that stretches across the narrow Montauk peninsula from the Long Island Sound to the Atlantic. Parts of it are heavily forested, best for mountain bikers or trail runners looking to get their miles in; the rest are open sand dunes that stretch onto a skinny, quiet beach on the sound, perfect for an adventurous walk or a picnic. Don't miss the Walking Dunes trail for its dramatic sandy bowls. In all, it's a respite from the rest of the Hamptons and a cool, totally unspoiled landscape to explore.

  • Courtesy Baron's Cove/©Trevor Tondro
    hotel

    Baron's CoveArrow

    $$ | Readers' Choice Awards 2017, 2018

    Baron’s Cove leans into the Hamptons lifestyle hard. If you don’t want to drop several million on a mansion, Baron’s Cove will give you a taste for the weekend. Located right along Sag Harbor cove, there’s a salt water pool in the summer, lounge chairs aplenty by said pool, and a preppy interior that looks like Ralph Lauren gave the decorator some tips. Guests can opt for a room that looks out onto the garden or the water. No matter where you stay, there will be nods to nautical design. With a full restaurant that services both guests and other visitors to Sag Harbor, you’ll never have to travel far for a meal here. But, this is the Hamptons, so prepare to shell out $25 for a breakfast sandwich or $26 for a lobster omelet at brunch. At dinner, opt for seafood options like the local catch of the day and a lobster caesar.

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    Parrish Art MuseumArrow

    $

    Driving down Route 27, you'll see what looks like a hyper-elongated modernist barn in an open field with two giant Roy Lichtenstein sculptures out front. This Herzog and de Meuron designed building is home to more than 2,600 works of art, many of them made by artists who lived and worked on the East End during their lifetimes, including Lichtenstein, Fairfield Porter, Willem de Kooning, and Dan Flavin. It's usually an older, quieter crowd—people are here to see the architecture and spend some time contemplating the art in the galleries. It never gets too crowded, unless it's a rainy day on a summer weekend.

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