The 13 Best Weekend Getaways Within 5 Hours of NYC

Lobster rolls, lighthouses, a luxury treehouse, and everything in between.

After the year we’ve just had, the simple act of traveling somewhere (anywhere!) because we finally can seems like enough of an excuse to hit the road. And while we’ve had plenty of moments to be present in the past 15 months, now is the time to lose track of time altogether—especially while drinking local wine, going on waterfall hikes, biking to seafood shacks, and roasting marshmallows like you're in a '90s summer-camp movie. 

But planning a trip can often take the fun out of it before you’ve even packed a bag, which is why we’ve made it easy for you to escape NYC by breaking down 13 perfect weekend getaways, all accessible within five hours by public transport or car. The only thing more essential than traveling is doing so responsibly, so be sure to review each destination’s COVID-19 guidelines before you hit the road.  

Most Underrated Getaway: The Inn at GrayBarns, CT

With its narrow, meandering roads lined with towering oaks, antique colonials, converted barns, riverfront A-frames, and little else, the Fairfield County hamlet of Silvermine isn’t an obvious draw for weekend travelers. That’s precisely why you’ll find yourself here, at the Inn at GrayBarns, a sublime un-Brooklynized nexus at which to gather with friends or just yourself and clock out. Rich in history yet refreshingly modern, GrayBarns has evolved from a 17th-century artist outpost to a 19th century textile factory, a roaring 20s speakeasy, and a 1960s hotel, which once hosted Hollywood honeymooners Elizabeth Taylor and Eddie Fisher.

Today, the adults-only property comprises a six-suite inn overlooking Guthrie Pond, a country store-cafe, and a farm-to-table restaurant prized by locals; book a seat on the patio and savor the cacio e pepe, burrata with rhubarb preserve, and Peach Tea-To’s cocktail, described by one diner as a “you-don’t-even-know-you’re-getting-drunk-Snapple.” While this hidden oasis is hard to leave, especially after a 60-minute deep tissue massage, take out one of the first-come, first-served Priority bikes and ask for the 1.8-mile waterfall-laden route. You’ll also want to slip away to a 49-acre sanctuary in neighboring New Canaan, centered around Phillip Johnson’s architectural marvel The Glass House, just a 10-minute drive from the hotel. When you get back, lounge in a Frette robe on your deck and pop a bottle of champagne from the complimentary mini bar, feeling remarkably revived, much like GrayBarns itself.

By public transit: Take a 60 minute ride on Metro-North to South Norwalk, then take a 10-minute Uber. 
By car: One hour
Where to stay (if not at the Inn at GrayBarns): Find a great Airbnb near GrayBarns

Best Food Getaway: Hudson, New York

With tons of destination eateries and boutique hotels like The Hudson MillinerThe Maker, and The Wick, this riverfront city rivals any restaurant row in the five boroughs. Upon arrival, go for brunch while social distancing in the lush garden at Red Dot, then walk off the gnocchi mac ’n cheese at all the galleries and vintage shops along Warren Street. After that, stop by café-motorcycle shop Moto Coffee Machine and bring an iced latte to explore the carriage trails and 250-acre grounds at Olana State Historic Site, a Victorian villa and the hilltop refuge of 19th century Hudson River School painter Frederic Church. On weekends, pick up Talbott and Arding's fried chicken feast, complete with buttermilk biscuits, old fashioned potato salad, and chili honey, and take it to the dreamy cocktail patio at women-owned Cooper’s Daughter Spirits distillery on Olde York Farm, a 10-minute drive from town. 

For dinner, hip farm-to-table spot Swoon Kitchenbar offers fresh seafood like pan-roasted salmon and oysters on the half shell, while Wm. Farmer and Sons seasonal menu has deliciously fresh creations like chicken thigh “nuggets” and perfectly crisp sunshine kabocha squash tempura along with a creative cocktail program of reinvented classics. For something desserty, cap the night with a visit to natural wine bar Sonder Hudson and pair the pound cake with cultured cream and berries with a bubbly bottle of Bairrada Espumante Rosa Pét-Nat from duck farmer-vintner, Joao Pato.

By public transit: Take Amtrak from Penn Station and get off at Hudson in two hours. Main Street is within walking distance of the station.
By car: 2.5 hours
Where to stay: Find a great Airbnb in Hudson

Harriman State Park
Harriman State Park | Flickr/Jason

Best Outdoor Getaway: Harriman State Park, New York

There’s plenty of great hiking and camping to do near NYC, but Harriman State Park—the second-largest state park in New York with over 47,000 acres and more than 200 miles of hiking trails—has it all. There are waterfalls, expansive views from atop Long Mountain, hammock-friendly trees by the lake, and few, if any, passersby to interrupt the peace and quiet.

For accommodations, choose between a cabin at the Harriman Outdoor Center, setting up camp at the park’s rustic Sebago Cabins, or booking the Adirondack Mountain Club’s Camp Nawakwa, then hike the moderate 4.5-mile Pine Meadow Trail that skirts a picturesque lake with boulders made for meditating or just cliff jumping. Post-hike, unwind at nearby coffee shop The Village Blend for an iced latte and croissant around one of the outdoor fire pits. 

By public transit: Take NJ Transit's Port Jervis Line out of Penn Station to Tuxedo in two hours. The 42-seat Harriman shuttle bus transports hikers from the Tuxedo train station to the trailheads for $5, and stops at a local farmers market and deli on Saturdays.
By car: 1 hour, 15 minutes
Where to stay: Find a great Airbnb by Harriman State Park

Most Affordable Getaway: Catskills, New York

A popular '60s retreat (hello, Dirty Dancing), the Catskills has experienced something of a renaissance over the last few years, while still remaining in reach of budget travelers. Though it’ll cost you just $35 to get to Phoenicia on the bus from Midtown, your best bet is to rent a car so you can make the most of your time in the Catskills. There are countless hip and affordable hotels to stay in, including Graham & Co (from $125/night) in Phoenicia; Kate’s Lazy Meadow (from $185/night) in Mount Tremper; Eastwind (from $279/night) in Windham; Hotel Dylan (from $149/night) in Woodstock; and Getaway (two-person cabins start at $159/night) in Catskill. Once you’re there, fly-fish, roast marshmallows, and dance on a log in the woods like Swayze would want you to.

For sustenance in Phoenicia, opt for the thin-crust wood-fired pies at old-school neighborhood joint Brio’s Pizzeria or cornmeal waffles at the Phoenicia Diner—both of which will give you all the energy you need to climb the highest peak in the Catskills (nearby Slide Mountain). In Bethel, home of the 1969 Woodstock Festival, start things off with a plate of fried chicken at The Dancing Cat Saloon, then walk next door to the Catskill Distilling Company to sip The Most Righteous Bourbon while looking out at a Storm King Art Center-inspired landscape.
By public transit: From Port Authority, ride the Adirondack Trailways bus for three hours to the center of Phoenicia.
By car: 2 hours
Where to stay: Find a great Airbnb in the Catskills

Montauk Lighthouse
Montauk Lighthouse | haveseen/Shutterstock

Best Bike Getaway: Montauk, New York

Board a morning train with your two wheels (remember to bring that $5 lifetime bike permit) and get off at the Westhampton station. From there, pedal about 45 miles along waterfront roads, through the Hamptons and out to Ruschmeyer’s hotel in Montauk, where you'll drop your backpack and cruise one mile to MTK Lobster House for a buttery overstuffed lobster roll to eat at South Edison Beach a few blocks away.

Ride five miles East to the historic Montauk Lighthouse and museum, situated inside the original 1860 keepers’ house. After touring a whaling exhibit and lingering at a display case with documents signed by Thomas Jefferson and George Washington, grab a Driftwood Ale at Montauk Brewing and reward a long, calorie-burning day with seared local sea scallops and fries at 668 The Gig Shack, conveniently located around the corner.
By public transit: Ride the LIRR from Penn Station two hours to the Westhampton station, where you’ll start your two-wheeled trip.
By car: 2.5 hours
Where to stay: Find a great Airbnb in Montauk

Best Beach Getaway: Newport, Rhode Island

The waves in this quintessential New England maritime town are clean, the seafood is fresh, and the beaches are uncrowded. After zipping up your wetsuit (rent them for $15/day at Rhody Surf), paddle out at either Easton's Beach or Sachuest Town Beach (known locally as First and Second Beach). Dry off with a bowl of squash soup and smoked salmon toast at newcomer Stoneacre Garden, or pick up fish tacos and street corn from Diego’s for a picnic at Fort Adams State Park. Visit the Tennis Hall of Fame, experience Newport’s Gilded Age along the Cliff Walk, and enjoy marina views over a bowl of fresh made tagliolini and “not your nonna’s meatballs” at Giusto at newly opened Hammetts Hotel.

Newport has a variety of accommodations year-round, whether you want to splurge at Castle Hill Inn (near a stunning hidden lighthouse), be charmed at the affordable 300-year-old The Clarkeston, or unwind at the coastal-inspired The Wayfinder.

Take home a bit of the Rhode Island seaside by picking up a bottle of Newport Sea Salt Co.’s hand-harvested sea salt from Le Bec Sucré, and order a pain au chocolat while you’re there. The Newport History Museum offers an in-depth virtual exploration of its exhibits inside the 1762 Old Brick Market building as well as an in-person tour of more than 300 years of rich local history. The museum’s guided walking tours ($15/pp) depart from the Colony House and cover topics such as Newport’s African American heritage and the Gilded Age.
By public transit: Take a Peter Pan bus from Port Authority or an Amtrak train from Penn Station to Providence for about three hours. Once in Providence, ride the Seastreak Ferry one hour to Newport.
By car: 3.5 hours
Where to stay: Find a great Airbnb in Newport

Best Cultural Getaway: Beacon, New York

Once an old factory town, Beacon has completely remade itself into both an art and food destination. Though it’s just an 80-minute rail ride up the Hudson River, boutique gems like the Roundhouse Beacon make it worth an overnight stay—lobster rolls on the terrace beside gushing Beacon Falls will be a highlight of the trip. 

On Main Street, fuel a day of gallery-hopping with French toast from BJ’s or a bacon, egg, and cheese from Mr. V’s Deli. If you’re hiking nearby Breakneck Ridge, you’ll need to refuel with a cold brew from café-cum-gallery Bank Square Coffeehouse and a donut from Glazed Over Donuts. Between visits to the myriad galleries, quirky independent shops, and hand-blown glass studios like Niche Modern and Hudson Beach Glass, grab a seat on the patio at the Hudson Valley Brewery for a pint of Capsule III or a sour farmhouse IPA brewed on-site.

Leave a few hours (and plenty of phone storage space for impromptu photo shoots) for Dia:Beacon, a 300,000 square foot former Nabisco factory that houses a collection of monumental contemporary works Like Richard Serra’s Torqued Ellipses, Dan Flavin’s light installations, and Sol LeWitt’s Isometric wall drawings. The museum is open by advance reservation only. Afterward, head to Denning's Point Distillery, for a $5 al fresco tasting of three different spirits, or cool off with the citrusy Blue Moon gin and Crème Yvette cocktail on the sidewalk—and make sure to bring home a bottle of the award-winning Beacon bourbon made from New York-farmed grains.

By public transit: Take an 80-minute Metro-North ride on the Croton-Harlem line to Beacon Station. It’s a five-minute walk to Dia:Beacon and 10 minutes from the hotel and Main Street.
By car: 1 hour, 45 minutes
Where to stay: Find a great Airbnb in Beacon

Best Family Getaway: Mohonk Mountain House, New York  

Perched on a cliff in New Paltz, the grand Mohonk Mountain House is a 152-year-old, all-inclusive resort for adults and kids. Throughout the 1,325-acre cliff-perched property, you’ll find tennis, golf, yoga, a spa, an indoor pool, boating on the lake and 85 miles of hiking trails—all easily accessible with a complimentary hotel ride from the nearby bus station in New Paltz.

By public transit: Ride the Greyhound bus to New Paltz station in one hour and 35 minutes or take Metro-North two hours north to Poughkeepsie.
By car: Two hours
Where to stay (if not at The Mountain House): Find a great Airbnb in New Paltz

Most Luxurious Getaway: Winvian Farm, Connecticut

As you pass through the white gates of Winvian, revel in the feeling that you've done something right in your life. The resort sprawls over 113 acres, where 18 designer cottages include a 35 foot-tall treehouse, a “secret society” temple, and a multi-level stable.

Activities include croquet, seasonal al fresco feasts on The Restaurant's stone patio, and complimentary mountain bikes to cruise around nearby Bantam Lake or visit Haight Vineyard along the CT Wine Trail. All of the cottages are completely unique, but equally outlandish—you can even sleep inside a fully restored 890-square-foot 1968 Sikorsky Sea King Pelican helicopter once used by the Coast Guard. The hotel can also arrange off-site diversions like horseback riding, hot-air ballooning, and clay shooting—and the 4,000-acre private White Memorial Nature Preserve is an eight-minute drive up the road for those looking to do a relaxed hike.

By car (your best option): 2 hours. The resort is also directly accessible via helicopter, if you're feeling particularly lavish.
Where to stay (if not at Winvian Farm): Find a great Airbnb near Winvian Farm

Best Boozy Getaway: North Fork, New York

Kick off your weekend in the Napa Valley of the East Coast (there are at least 60 vineyards!) with a glass of stainless steel-fermented chardonnay at Sherwood House Vineyards (currently reservations-only), then move farther East to Lieb Cellars—tucked away on Oregon Road—for Bridge Lane rosé and bucolic views off the patio. Get a Bang Bang Shrimp and Baja tacos with a side of spicy fried cauliflower at Mattitaco and take it to Nassau Point, a beautiful spit of sand (unknown even among locals) in Cutchogue. Next, head to the Greenport Brewing outpost in Peconic for a crisp pint of Haus Pils and a giant salty pretzel. Be sure to stock up on fresh produce at Sang Lee Farms8 Hands Farm, and Country View Farm Stand before going home. The best North Fork experience is had on a whim, be it by car, or with Dan’s Bike Rental, which will meet you at the train station with a 21-gear hybrid-style Trek bike and plenty of insider tips.

By public transit: Board the Hampton Jitney for a three-hour ride or the LIRR from Penn Station to Mattituck in two hours and 40 minutes.
By car: 2 hours
Where to stay: Find a great Airbnb in North Fork

Saint-Gaudens National Historic Site
Saint-Gaudens National Historic Site | Jeffrey M. Frank/Shutterstock

Best College Town Getaway: Hanover, New Hampshire

Ivy League towns don’t get better than Dartmouth's home of Hanover, New Hampshire with its gorgeous green backdrop, great local food scene, vibrant art collections, and old-fashioned Main Street—where you can even start hiking the Appalachian Trail.

Check into the Hanover Inn, which overlooks the Dartmouth Green, and consider your options: grab a six-pack of Smuttynose and a sandwich from Umpleby’s and lounge in the grass; kayak on the Connecticut River with Hanover Adventure Tours; visit the Saint Gaudens National Historical Park; or simply roam the charming downtown and regal campus. No matter how you spend the day, you're starting with “The Big Green” platter of French toast, two eggs, cob-smoked bacon, sausage, home fries, and a muffin on the patio at Lou’s (a local breakfast tradition since 1947), having dinner on the terrace at celebrated farm-to-table restaurant Pine, and grabbing a nightcap (or pregame drink if it’s that kind of night) at Murphy's on the Green.

By public transit: Dartmouth Coach departs East 42nd between Lexington and Third Avenue and drops passengers off next to the Hanover Inn in under five hours.
By car: 4 hours
Where to stay: Find a great Airbnb in Hanover

Best Mountain Getaway: Hunter, New York

Hunter may be primarily known as a popular ski destination, but there’s plenty to do off the slopes, like hiking to Kaaterskill Falls, mountain biking, and flying over 50 mph on the longest and highest zipline in North America. Check in to the ultra-modern Scribner’s Lodge, a 38-room former 1960s motor lodge that offers 270-degree deck views of the Catskill Mountains, an outdoor fire pit, complimentary masks, and a mountain concierge for all your adventure needs. Prospect, the hotel’s on-site restaurant, offers sharable Alpine-inspired and Hudson Valley-foraged dishes. In nearby Tannersville, get the blueberry pancakes at Maggie’s Krooked Café and Mama’s Boy Burgers’ grass-fed cheeseburger.

By public transit: Take the Adirondack Trailways bus from Port Authority to Tannersville for three hours, then a five-minute cab ride to the lodge.
By car: 2.5 hours
Where to stay: Find a great Airbnb in Hunter

Best Romantic Getaway: Finger Lakes, New York

If North Fork wine country isn’t enough of a far-flung weekend destination, consider a trip upstate. The Finger Lakes region is known for its 11 lakes, beautiful rolling farmland, quaint towns, and outdoor adventure—but its vineyards are the main draw.

Drink Thirsty Owl Wine Company’s riesling along the Cayuga Lake Wine Trail, sip the sauvignon blanc at Fulkerson Winery, or tap into the burgeoning brewery scene—Climbing Bines offers 10 tastings, live music and corn hole. Break up all the boozing with an outdoor activity: a visit to Watkins Glen State Park with its 19 waterfalls, a bike ride along the lakes, a Canandaigua Lady cruise, or purchase advance tickets to the newly expanded Corning Museum of Glass, where you can blow your own piece of glass art. For lunch, settle on Red Newt Bistro’s patio with beautiful country views, gourmet grilled cheeses, and a riesling flight, then cozy up by the fire in the library room at the newly opened The Lake House on Lake Canandaigua.

By public transit: Take the ShortLine bus from New York to Elmira for five hours.
By car: 4 hours
Where to stay: Find a great Airbnb in the Finger Lakes

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Lauren Matison is a freelance writer about to embark on a cross-country campervan trip from Connecticut to California. Follow Lauren on Instagram (podcast recs welcome!).