Post Overview: Best Weekend Trips from NYC

As fun as New York City is, sometimes you just need a break. The fast-paced, concrete jungle (and expense of everything) has a way of compounding and sometimes the reset button is begging to be smashed.

If you’re like 80% of America working Monday through Friday the only window of opportunity to do so is on the weekend. Fortunately there’s more than a few noteworthy destinations near the city.

In this article I’ll go over the best weekend trips from NYC, breaking them down by mode of transportation. I’ll try to keep travel under five hours (each way) so you can make the most of your time.

But let’s cut the small talk. We have a lot of ground to cover, so let’s dive right in.

Visiting New York City? If you haven’t decided where to stay (yet) check out our helpful guide on Where to Stay in New York City (The best neighborhoods for first timers +2 to avoid). Don’t have time? Here’s our favorite hotel in NYC, hands down.

Weekend Trips From NYC

Best Weekend Trips from NYC (By Car)

Princeton, NJ

Drive time: 1 hour 30 minutes

Home to one of the most prestigious universities in the country, Princeton, New Jersey is one of the best weekend trips from NYC for history buffs and those seeking to escape the city for a bit.

The university is the Alma Mater of Michelle Obama, three Supreme Court justices, Jeffrey Bezos and countless other heavyweight names. Who’s to say you won’t be at a bar sharing drinks with the next President of the U.S?

Thanks to Princeton University there’s a plethora of fun things to do besides go to class. The Princeton Art Museum, Princeton University Chapel and Morven Museum & Garden are all highlights on campus.

Outside of the University, Princeton is like most college towns. Quaint and full of character, there’s a variety of cafes and bars that will keep you well fed during your weekend trip from NYC.

Word to the wise: Halo Pub in Princeton makes ice cream using milk from its own dairy farm, it’s a must-stop. Your sweet tooth has finally met its match.

The Catskills, NY

Drive Time: 2 to 3 hours

The Catskill Mountains have seen a boom in popularity, but it doesn’t take a rocket scientist to see why.

It’s peaceful in the way only a quiet, undisturbed place can be. A trip into the mountains is the perfect weekend getaway from NYC for those who want to unplug and unwind.

There’s a few destination towns of note in and around the Catskills, including the town of Catskill itself along with Windham, Woodstock (yes, this is where the festival took place), Monticello and New Paltz.

In reality though I wouldn’t choose where to stay in the Catskills solely based off the town, I’d do so based off the hotel. The Catskills has been a hotbed for boutique hotels and resorts in recent years, going viral left and right.

A few of the best include Piaule in Catskill, Inness in Accord, and Getaway Western Catskills in Roscoe. They all use the same recipe for success – individual cabins with views of the forest and a resort full of relaxing amenities.

But even if your weekend trip from NYC doesn’t include a stay at one of these fancy resorts, you’ll come to appreciate the abundance of hiking trails and outdoor activities in the Catskills.

Saratoga Springs, NY

Drive time: 3 hours

Saratoga Springs is one of the all-around great weekend trips from NYC. Regardless of your interests, who you’re traveling with or budget, everyone can have a good time in Saratoga Springs.

The small city’s claim to fame are its mineral springs, which can be found throughout town. Even before the arrival of European settlers the mineral springs attracted Native Americans for their healing properties.

The city’s also home to the Saratoga Race Course, one of the oldest horse tracks in the country.

The course hosts races five days a week from mid-July through early-September. Or if you want something less serious, the Saratoga Casino Hotel also has a track (and you can hit the slots, cha-ching).

But if you were in search of weekend trips from NYC where you could just sit by the water, Saratoga Springs checks that box too. Saratoga Lake is a picturesque setting to sit by the fire on the shore or even ride a boat.

The Adirondacks, NY

Drive time: 3 to 5 hours

Similar to the Catskill Mountains, the Adirondacks are a nature-nut’s dream come true.

Full of hiking trails, more than 200 lakes and a plethora of wildlife it’s a rejuvenating reprieve from the concrete jungle. You just have to decide how much you want to rough it, you can camp or stay in town at a hotel.

And lucky for you, the Adirondacks have a plethora of charming villages to choose from, nearly all of which are near (and named after) lakes. Lake Placid, Saranac Lake and Tupper Lake are all in the heart of the Adirondacks and make for charming weekend trips from NYC.

Once you set up base and get checked into your room I strongly encourage you to explore the mountains.

You can hike as much or as little as you want, but places like the Ausable Chasm (nicknamed the Grand Canyon of the Adirondacks), the High Falls Gorge and Avalanche Lake are too beautiful not to see with your own eyes.

Woodstock, VT

Drive time: 4 hours 30 minutes

One of the best weekend trips from NYC in the fall is anywhere in Vermont, the state is set ablaze in shades of yellow, orange and red that’ll leave your jaw on the floor.

But if I have to recommend only one destination it’d be the tiny town of Woodstock. From here you’ll have access to a the full array of colors and attractions all around.

The Sleepy Hollow homestead is a destination for fall photo-shoots, and the Middle Covered Bridge is just as charming. Bring an empty memory card because your camera will be full come time to go home.

From Woodstock you’re only an hour and a half away from Burlington, Vermont on Lake Champlain and the state capital in Montpelier. The state is at your fingertips!

But if you’d rather relax and stay in town you won’t be short on things to do. There’s farmer markets, the Billings Farm & Museum and the Marsh-Billings-Rockefeller National Historical Park.

Portland, ME

Drive time: 5 hours

The most idyllic and charming coastal weekend trip from NYC, Portland Maine feels surreal.

The cobblestones streets and lighthouses give the city a timeless vibe, but the abundance of bars and trendy restaurants help keep it youthful and fun.

It’s one of the best weekend trips from NYC for foodies, especially those into seafood. Lobster rolls are non-negotiables, potato donuts are heaven-sent and the bar scene is no slouch.

Mix in some of the popular attractions like the Portland Museum of Art, Old Port, Portland Observatory and the Victoria Mansion you’ll have more than enough reason to plan a return trip.

Portland Maine, best weekend trips from NYC

Best Weekend Trips from NYC (By Train)

The Hamptons/Montauk

Travel time: 2 to 3 hours

Could I start any other way? If you say “weekend trip from NYC” to any local, nine out of ten will immediately think of the Hamptons.

Whether they’ve been or not, a weekend getaway and the Hamptons are practically synonymous. Famous for being full of millionaires and sandy beaches, you’ll also come across plenty of young spring-breakers and the like.

And before there’s any confusion I have to explain The Hamptons is named so because it’s a conglomerate of a handful of towns that end in “ampton” like Southampton, Bridgehampton, and East Hampton.

The whole southern fork is often referred to as the Hamptons, and Montauk which is the neighboring town is often roped in too.

The stretch of insanely priced real-estate is at the end of Long Island on the southern fork. In 2023 the average price for a home in Hamptons broke $3 million, but luckily you’re just here for the weekend.

The insane price-tag means this is one of the best weekend trips from NYC to take with friends. Airbnb’s will be pricey but most ~~houses~~ mansions are big enough to house a few couples meaning you can split the cost.

The major plus to taking a weekend trip from NYC to the Hamptons is that getting there is easy as pie. Just get tickets for the Long Island Rail Road (LIRR) and ride that baby to your beach vacay.

North Fork, Long Island

Travel time: 3 hours

Opposite of the Hamptons is the North Fork of Long Island, and it’s just as worthy of being one of the best weekend trips from NYC.

The best thing the North Fork has going for it is that it’s not named the Hamptons, so the price tag is trimmed and easier to swallow. It shares in the New England coastal charm but has less crowds, making it a quieter getaway.

The North Fork is also home to more than 30 vineyards, making it a sought-after destination for romantic weekend trips from NYC.

And contrary to the Hamptons, the North Fork’s peak tourist season is in the fall. Thanks to a handful of multi-generation farms hosting pumpkin patches and the like, autumn is the one time you might run into traffic.

And like the Hamptons, North Fork is accessible via the LIRR. The Greenport stop will put you right in the middle of the action and have the best options for lodging.

Hudson Valley, NY

Travel time: 1 hour 45 minutes

Perfect for outdoor enthusiasts and relaxation-seekers alike, the Hudson Valley is an underrated gem.

The valley runs along the entirety of the Hudson River, but for the sake of this article I’ll focus on the towns of Beacon & Cold Springs, both of which are accessible via train.

The Hudson Line makes the stop at both towns, opening the door to the Hudson Valley to city slickers like you and me. Both Beacon & Cold Springs offer a small town charm that’s hard

Both towns have that small town charm and are full of quirky cafes and markets. Beacon is home to Dia Beacon, a popular art museum and also has a castle you can tour (which used to be a military warehouse).

On the other hand Cold Springs is a worthy competitor. It has less of a tourist town vibe, and more of an quiet, undisturbed town atmosphere.

The Hudson Highlands State Park will have you grinning from ear to ear in between the heavy breaths (hiking kicks my butt, too) Moo Moo’s creamery is the perfect post-hike snack: ice cream.

Baltimore, Maryland

Travel time: 3 hours 30 minutes

I won’t deny the fact that Baltimore has been in the news for rising crime rates, but lets be honest, is there any major city not making headlines?

If you take a weekend trip from NYC to Baltimore you’ll have plenty of fun enjoying the major sites.

There’s more than one museum (the Baltimore Museum of Art is my fav, and it’s free!) and your stomach won’t know hunger within the gastronomical hotbed.

The National Aquarium also comes highly recommended, but if I’m honest I’ve never been.

Truth be told, Baltimore is one of the best weekend trips from NYC so long as you make an itinerary. In my experience it’s not the kind of place worth getting lost in, but if there’s something you want to see go for it.

The Berkshires, MA

Drive time: 3 hours

Berkshire (commonly known as the Berkshires) is a county in Massachusetts that’s become such a popular weekend trip from NYC that Amtrak created its own proprietary line: the Berkshire Flyer.

From May through October the Berkshire Flyer departs Penn Station every Friday at 3PM and returns every Sunday at at 7PM. Tickets go fast though, so secure your seat ASAP!

Once you’re in the Berkshires the world is your oyster. The region is full of hiking and ripe with opportunities to reconnect with nature.

The train drops you off in the small city of Pittsfield, so we’ll use that town as our base of operations. From here you’re at the front door of Pittsfield State Forest, the Appalachian Trail, winter sports and more.

Depending on the route you choose to pursue the Berkshires can serve as a romantic getaway from NYC, a family vacation or a solo trip used to clear your head. The county really is a jack of all trades!

Boston, MA

Travel time: 4 hours 30 minutes

We all grew up learning about the Boston Tea Party in school, now you get to visit the place where it all went down.

Boston Massachusetts is a history buffs playground, an Instagrammers dream come true and the reason behind a foodie’s smile. Seriously, from the Museum of Fine Art to the Quincy Market you won’t be short on things to do.

Depending on when you visit, you can also check out a Boston sporting event. The Boston fan base is notoriously loud and unrelenting, the kind of folks you don’t want to face – but when you’re a part of them it’s a hoot.

It’s one of the few weekend trips from NYC you can enjoy time and time again, each time experiencing something new. My wife and I have been four times, and already have a trip booked for a fifth!

Salem, MA

Travel time: 5 hours

If there’s one destination I want to embed in your brain it’s Salem Massachusetts – but it has to be in October!

This is one of the best themed weekend trips from NYC, so don’t forget to pack your costume. 😉

Braving the crowds is a small price of admission, the notorious town goes all out for Halloween. Witch hats stick out like beacons from among the crowds, cobwebs and hay bales are in front of every storefront and spirits are high.

And as if the decor wasn’t charming enough, the town looks like it came out of a movie. Red brick buildings and pedestrian-only streets make Salem feel extra festive.

To get there you’ll have to take the train from New York to Boston and from Boston to Salem, but the transfers are worth one of the best weekend trips from NYC.

Providence, RI

Travel time: 4 hours

The capital of Rhode Island, Providence is accessible via train and one of the best weekend trips from NYC.

As one of the oldest towns in America (founded in 1636) you can easily spend the day visiting the countless historical sights. If you only have time for one though I recommend touring the Rhode Island State House.

If you’re a fan of the arts you can catch a show at the Providence Performing Arts Center or peruse the The Museum of Art, Rhode Island School of Design.

And if you’re enjoying a weekend trip from NYC with kids peruse the Providence Children’s Museum.

It won’t take long to see Providence is a town rich in art and history, making it one of the best weekend trips from NYC.

Philadelphia, PA

Travel time: 2 hours

The City of Brotherly Love, Philly, the Qauker City, no matter what you call it Philadelphia is one of the best weekend trips from NYC.

Take time to see the Liberty Bell, the Museum of the American Revolution or Independence Hall so you can learn about the origins of America. Or take a stroll down Elfreth’s Alley, the oldest residential street in America.

There’s a lot of history to be learned and appreciated in Philadelphia, but that goes without saying.

If you work up an appetite Philadelphia won’t let you go hungry. Have a bite at any restaurant in the Midtown Village neighborhood and trust me when I say you’ll want to stick around for drinks.

Washington D.C.

Travel time: 4 hours

You know I couldn’t make a list of the best weekend trips from NYC and not include the nation’s capital.

Washington DC is four hours away via train and once your there the Metrorail can take you just about anywhere you want to go.

There’s an abundance of landmarks that you’ll never get through in two days, so you’re going to have to plan a return trip. If you want to squeeze in the museums? Might as well look into staying for a week.

But a weekend trip from NYC is more than enough to wet your toes a little bit. You can get the iconic photos in front of the White House, Lincoln Memorial and the Washington Monument and taste what D.C. is like.

And speaking of tasting, Washington D.C. boasts the fourth-most Michelin stars of any other place in America. To call it a foodie haven would be an understatement, so bring your appetite.

Best Weekend Trips from NYC (By Plane)

Orlando, FL

Flight time: 2 hours 30 minutes

Need I say more? Flights are only two and a half hours from New York City to Orlando, so you can be there and back with time to spare for that Monday morning Zoom call.

Although Orlando is inland and not on the beach, it still has the toasty beach weather you’re craving.

Orlando is one of the best weekend trips from NYC for families because it’s home to the happiest place on earth, Disneyworld. In fact it’s the largest Disney in the world, so you might need to book a second trip.

But if Mickey gives you the creeps there are more than a dozen other theme parks, including Universal Studios. You’ll love an adrenaline filled weekend riding coasters, but don’t scream too much or you’ll lose your voice.

End your night with drinks and a little boogie at any of one Orlando’s bars. The nice weather means you can stay out until the wee hours of the night in just a t-shirt and not be miserable bar hopping.

Montreal, QC, Canada

Flight time: 1 hour 30 minutes

O Canada!, Our home and native land! Bring your passports because one of the best weekend trips from NYC involves visiting our neighbors to the north.

The second largest city in Canada, Quebec has everything you could ever want. A vibrant food scene? Check. World-class museums? Check. Seasonal events including sports, festivals and expositions? Check.

Once you’re in Montreal getting around is a breeze thanks to the public transportation system. New Yorkers will feel right at home riding the metro, which costs $3.50 CAD a ride.

The only thing to be weary of is the winter chill, because when it bites you it hurts. December through February the average temperature is below freezing, and in March it doesn’t get much better creeping up to 35°F.

Toronto, ON, Canada

Flight time: 1 hour

Staying north of the border you have Toronto, the most populous city in Canada. As one of the best weekend trips from NYC, Toronto is a charming city that’s loaded with enough attractions to keep you busy for days.

World-class institutions like the Royal Ontario Museum, the Ontario Science Center and Art Gallery of Toronto will help keep you busy during your weekend trip from NYC.

And landmarks like the CN Tower, St. Lawrence Market and Casa Loma are worthy photo-ops for Instagram and to send to your mom.

More so than a getway or a vacation, Toronto is a fun weekend trip from NYC for those who want to see new places. It’s not an entirely different change of pace from New York, so it’s not a reset, just a fun pit-stop.

Virginia Beach, VA

Flight time: 1 hour 20 minutes

Found where the Chesapeake Bay meets the Atlantic Ocean, Virginia Beach is a popular weekend trip from NYC in the summer. As the name implies, it’s sought-after for its beaches.

Less crowded than the white sand beaches of Florida but still full of young travelers, Virginia Beach is a great place to party. The nightlife is thriving and you’ll find more than a few watering holes open late.

But the charming coastal town vibe also makes it romantic and family-friendly. Attractions like the Military Aviation Museum, the Atlantic Fun Park and the Hunt Club Farm are all worthy pit-stops.

So if summer in the city is too hot for you consider taking one of the best weekend trips from NYC to Virginia Beach and hang out by the water.

Quick recap of the best weekend trips from New York City

Princeton, NJ
The Catskills, NY
Saratoga Springs, NY
The Adirondacks, NY
Woodstock, VT
Portland, ME
The Hamptons / Montauk
North Fork, Long Island
Hudson Valley, NY
Baltimore, Maryland
The Berkshires, MA
Boston, MA
Salem, MA
Providence, RI
Philadelphia, PA
Washington D.C.
Orlando, FL
Montreal, QC, Canada
Toronto, ON, Canada
Virginia Beach, VA