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15 Top-Notch Weekend Trips From New York City (Worth The Effort)

Shopping in Woodstock, Vermont in the Fall, Best weekend Getaways from NYC

As fun as New York City is, sometimes you just need a break. The busyness (and expense of everything) can be overwhelming, and the reset button starts looking awfully tempting.

If you’re in need of reprieve I’ve got you covered. In this article I’ll go over the best weekend trips from NYC, breaking them down by mode of transportation. I’ll keep travel under five hours (each way) so you can make the most of your time. Speaking of maximizing time, let’s get to it!

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 +3 to avoid). Don’t have time? Here’s our favorite hotel in NYC, hands down.

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Best Weekend Trips From NYC

Table of Contents: Best Weekend Getaways from New York City

Walking through Woodstock, Vermont in the Fall, Best weekend trips from NYC

Woodstock, VT

Drive time: 5 Hours 15 Minutes
Where to stay: The Village Inn Of Woodstock

One of the best weekend trips from NYC (especially in the fall) is to anywhere in Vermont. The great state is set ablaze in shades of yellow, orange and red that’ll leave your jaw on the floor. However, if I have to recommend only one destination it’d be the tiny town of Woodstock.

Nestled in the heart of the Green Mountains, Woodstock offers a serene and charming atmosphere that provides a refreshing contrast to the urban pace. Renowned for its historic architecture, vibrant arts scene, and the iconic covered bridge over the Ottauquechee River, Woodstock exudes a timeless appeal that situates it well among the best weekend getaways from New York City.

Princeton, NJ

Drive time: 1 hour 30 minutes
Train time: 2 hours
Where to stay: Hyatt Regency Princeton

Princeton, New Jersey, packs a weekend wallop for day trippers and adventurers coming from NYC. Think Ivy League history whispering through sun-dappled courtyards, gourmet bites hidden in quaint cafes, and nature’s embrace within sprawling state parks.

Here, history buffs stroll the same grounds Einstein strolled, foodies can enjoy Michelin bites, and culture vultures feast on world-class art. It’s a town where academia, artisanal flavors, and outdoor adventure find rhythm, promising a weekend getaway far removed from the urban hum of New York City.

The Catskill Mountains, NY

Drive time: 2 Hours 40 Minutes
Where to stay: Piuale Catskill (Luxury) & Union and Post (Mid-Range)

Trade towering skyscrapers for soaring peaks, and honking taxis for the rustle of leaves at the Catskill Mountains. As one of the most adventurous weekend trips from NYC, The Catskills pack a punch for outdoor-enthusiasts of all stripes.

Think scaling Kaaterskill Falls, a majestic cascade you can walk behind, or kayaking the glassy expanse of Lake Minnewaska. Hike hidden trails teeming with vibrant fall foliage, bike scenic backroads past charming villages, or conquer the dizzying heights of Hunter Mountain. Come nightfall, trade the city lights for fireflies and starry skies, enjoying one of the best weekend trips from NYC.

Saratoga Springs, NY

Drive time: 3 Hours 30 Minutes
Train time: 5 Hours
Where to stay: The Inn at Saratoga

Saratoga Springs is a charming resort town nestled just hours from NYC. There’s a charming Victorian elegance, where grand hotels whisper tales of the Gilded Age, and natural mineral springs bubble up, promising rejuvenation for body and soul.

Imagine stepping back in time on Broadway, Saratoga’s main street, its historic buildings boasting intricate details and trendy shops. Trade honking taxis for the clip-clop of horse-drawn carriages, or catch a thrilling race at the iconic Saratoga Race Course, where thoroughbreds thunder down the track.

For the adventurer, Saratoga Spa State Park beckons with miles of hiking trails, glistening lakes perfect for kayaking, and even geothermal geysers erupting from the earth. Soak in the famed mineral springs, said to possess healing powers, while enjoying one of the best weekend getaways from NYC.

Lighthouse in Portland, Maine, Weekend Trips from NYC

Portland, ME

Drive time: 5 Hours 30 Minutes
Where to stay: Portland Regency Hotel & Spa

Ditch the skyscrapers for salty breezes and lobster rolls! Portland, Maine is a coastal charmer bursting with maritime history, culinary delights, and adventurous spirit. Imagine cobblestone streets lined with colorful houses, harbor views dotted with bobbing sailboats, and fresh seafood at every table.

Explore the working waterfront where schooners once sailed the seas. Hike clifftop trails overlooking crashing waves, or kayak through hidden coves. For a touch of history, delve into the Portland Museum of Art‘s renowned collection. You can also wander the historic Old Port, a maze of brick buildings filled with unique shops, cozy cafes, a slew of bars that are brimming with foamy brews!

The Hamptons/Montauk

Drive time: 2 Hours
Train time: 2-3 Hours
Where to stay: Depends on the Town + Experience

If you say “let’s go on a weekend trip” to a New Yorker, most will immediately think of the Hamptons. The charming string of seaside villages are just a hop, skip, and ride on the Long Island Railroad away from NYC. The cozy harbor towns are adorned with quaint boutiques and art galleries, pristine beaches begging for barefoot walks, and charming cafes spilling onto flower-lined streets.

You can explore Southampton’s historic mansions, wander East Hampton’s art galleries, or cycle through Montauk’s wild beauty. The Hamptons has something for everyone, and that’s why it’s one of the best weekend trips from NYC.

In 2023 the average price for a home in Hamptons broke $3 million, but luckily you’re just here for the weekend. The price-tag means this is one of the best weekend trips from NYC to take with friends, so long as you find an AirBnB big enough to split the cost with friends.

North Fork, Long Island

Drive time: 2 Hours
Train time: 3 Hours 30 Minutes
Where to stay: Sound View Greenport

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 manage. On top of that, the peak tourist season is in the fall making it even more affordable, to boot.

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 (Kontokosta is a non-negotiable!), that help make it a sought-after destination for romantic weekend getaways from NYC.

Atlantic City, NJ

Drive time: 2 Hours
Train time: 3 Hours
Where to stay: Hard Rock Hotel & Casino

A quick train ride or drive from NYC lies Atlantic City, a vibrant seaside escape ready to shake up your weekend. Imagine waking to the rhythmic rumble of waves, swapping honking taxis for seagull cries, and trading concrete canyons for endless stretches of sand.

But Atlantic City’s magic goes beyond beach bliss. Craving thrills? Ride the iconic ferris wheel at Steel Pier, test your luck at the glittering casinos, or zipline over the Boardwalk for an adrenaline rush. Feeling adventurous? Kayak through back bays teaming with birds, bike along scenic coastal paths, or climb Absecon Lighthouse for breathtaking ocean views.

For a dash of relaxation, sink into a beach chair with a cool drink, build sandcastles with the kids, or catch a sunset with your sweetie. You might assume that Atlantic City is a sin-city with nothing to do but gamble, but it’s surprisingly one of the best weekend trips from NYC for families.

The Berkshires, MA

Drive time: 3 Hours
Train time: 3 Hours 30 Minutes
Where to stay: Black Swan in Lee

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, talk about convenience!

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, it’s one of the best weekend trips from New York City for the outdoorsy types. The train drops you off in Pittsfield, so you’re at the front door of Pittsfield State Forest, the Appalachian Trail, winter sports and more.

Best Weekend Trips from NYC, Walking outside the Quincy Market in Boston Massachusetts

Boston, MA

Drive time: 3 Hours
Train time: 4 Hours
Where to stay: Anywhere in Beacon Hill

Boston’s rich history, vibrant culture, and diverse culinary scene make it an ideal destination for a NYC weekend getaway. In a lot of ways Boston is a cleaner, simpler, more charming New York; so it’s a perfect weekend trip for city-slickers who break out in hives at the thought of going on a hike.

Stroll along the historic Freedom Trail, explore world-class museums, or savor the delectable seafood at Quincy Market. Whether you’re seeking an intellectual retreat at Harvard or a relaxing weekend getaway from New York City along the Charles River, Boston’s charm is bound to captivate.

Boston’s also one of the few destinations around New York City you can visit time and time again. You’ll never experience all there is to eat, drink or see in one trip. Maybe that’s why my wife and I have already enjoyed two weekend getaways to Boston, and have a third on our radar for later this year.

Halloween in Salem Massachusetts, Best weekend getaways from New York City

Salem, MA

Drive time: 4 Hours
Where to stay: Salem Waterfront Hotel & Suites

If there’s one destination I want you to remember it’s Salem Massachusetts – but it has to be during Halloween! 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 All Hallows Eve. Witch hats bob between crowds and cobwebs & hay bales sit in front of every storefront. The town looks like it came out of a movie, too. Red brick buildings and pedestrian-only streets make Salem one of the most charming (and during Halloween, creepy) weekend getaways from New York City.

Providence, RI

Drive time: 4 Hours
Train time: 3 Hours 30 Minutes
Where to stay: The Dean Hotel

As one of the oldest towns in America (founded in 1636), Providence, is one of the best weekend trips from NYC for history buffs. It’s the capital of Rhode Island so I recommend touring the Rhode Island State House or exploring the The Museum of Art, Rhode Island School of Design.

Wander through the charming streets of College Hill or savor culinary delights at WaterFire events along the river. This city effortlessly caters the adventurous types just as effortlessly as it does to those seeking relaxing weekend getaways from New York City.

Philadelphia, PA

Drive time: 2 Hours
Train time: 2 Hours 30 Minutes
Where to stay: Hyatt Centric Center City Philadelphia

Philly, just a train ride away from NYC, packs a surprisingly diverse weekend punch, whether you’re a history buff itching to see the Liberty Bell, a foodie chasing their cheesesteak dreams, or an adventurer eager to explore vibrant street art districts.

Imagine strolling cobblestone streets lined with Revolutionary War-era houses or climbing the steps at the Philadelphia Museum of Art like Rocky himself. But Philly’s not stuck in the past. Kayak down the scenic Schuylkill River, bike through hipster havens like Rittenhouse Square, or catch a game at the iconic cheesesteak-scented Citizens Bank Park!

Washington D.C.

Drive time: 4 Hours 30 Minutes
Train time: 3 Hours 30 Minutes
Where to stay: Lyle DC

Washington DC is four hours away via train and once you’re in the city 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, but a weekend trip from NYC is more than enough to wet your toes.

The soaring Washington Monument and echoing depths of the Lincoln Memorial will have you itching to see more. Just forget the mandatory photo in front of 1600 Pennsylvania Avenue.

Plus, Washington D.C. boasts the fourth-most Michelin stars of any city in America. To call it a foodie haven would be an understatement, so don’t forget to pack your appetite on this quick weekend getaway from NYC.

Quick recap of the best weekend trips from New York City

  1. Princeton, NJ
  2. The Catskills, NY
  3. Saratoga Springs, NY
  4. Woodstock, VT
  5. Portland, ME
  6. The Hamptons / Montauk
  7. North Fork, Long Island
  8. Hudson Valley, NY
  9. Atlantic City, NJ
  10. The Berkshires, MA
  11. Boston, MA
  12. Salem, MA
  13. Providence, RI
  14. Philadelphia, PA 
  15. Washington D.C.

Weekend trips from NYC (Helpful Map)

The reason you might need a weekend trip: 20 HONEST Pros & Cons of Living in New York City

Where to enjoy a staycation: 15 Great Public Pools in New York City (To Beat The Heat)

How to let people know where you’re from: 10 New York City Slang Words

How to save money while in NYC: 20 Unique Free Things to Do in New York City

The best things to do in NYC: 30 Best Things to Do in New York City (For First Time Visitors)

Frequently Asked Questions
What is the best road trip from New York?

A fall foliage road trip to Vermont is the best road trip from New York City. The state is brimming with vibrant shades of red, yellow, and orange that are impossible to resist.

What cities are 2 hours from New York City?

Princeton, Montauk, and Philadelphia are some of the best cities located a mere two hours from New York City, making them easy weekend getaways.

What are the best weekend getaways in the Tri-State area?

The Hamptons, the Catskills, the Hudson Valley and Princeton, New Jersey are some of the best weekend getaways in the Tri-State area.

What are the best outdoorsy weekend getaways from New York City?

The Catskills and the Hudson Valley are some of the best outdoorsy weekend getaways from New York City. Most of these locations also happen to be accessible via train.

And there it is my friends, a roundup of the best weekend trips from NYC. As always, don’t hesitate to let us know if we missed anything.