Most Popular Day Trips from New York City, NY

Got a few extra days on your NYC visit? Experience life outside of the Big Apple on some of the best day trips from New York City! Within just a few hours of the “City That Never Sleeps,” a plethora of intriguing travel destinations, from gorgeous state parks like Bear Mountain to historic cities like Philadelphia, PA. Plan your escape from the city buzz with this complete guide to the top-rated New York City side trips!

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Bear Mountain State Park, NY

Recommended for outdoor activities

1 hour and 30 minutes

Need to get out of the concrete jungle and out into the wilds of nature? Drive just over an hour north of New York City to the natural wonderland that is Bear Mountain State Park, NY. Located on the west bank of the Hudson River in Upstate New York, this state park offers visitors every outdoor pursuit possible.

Bear Mountain State Park, NY

Begin your side trip to Bear Mountain State Park at the Trailside Museum and Zoo. Learn more about the upkeep and geology of this majestic 5,205-acre state park. Enjoy hearing all about the rescue and rehabilitation program of the various native animals in the small zoo area before heading out onto the trails.

Speak to experts at the museum or zoo to help pick the right hiking trail for you. Wander through the woodlands, around the river, and through the mountains, taking in the breathtaking vistas. You can hike, bike, swim, run, or sail around the park.

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Visiting in the winter months? Bear Mountain State Park is home to world-class cross-country skiing and sledding routes, as well as plenty of ice skating opportunities. It’s truly an outdoor lovers’ paradise and the perfect antidote to the hustle and bustle of the Big Apple!

Philadelphia, PA

Recommended for historical sightseeing

2 hours

Looking for a day out in a smaller, historic US city? Take a journey about two hours southwest into neighboring Pennsylvania to explore Philadelphia. As the original US capital city, Philadelphia is bursting with historical buildings, museums, and artifacts, making it the perfect stop for any US history buff.

Philadelphia, PA

Commence your one day in Philadelphia at the legendary Independence Hall. Learn about the birth of the nation and take in the iconic Liberty Bell. Take a snap and read the plaque before moving on to your next stop.

Are you a fan of the Rocky movies? Maybe you’re an art lover? Whichever suits you, you’ll want to run up the 72 steps of the Philadelphia Museum of Art. Made famous by Sly Stallone’s iconic training montage, the Philadelphia Museum of Art is also home to plenty of stunning artwork, including pieces by Picasso, Rodin, and Van Gogh.

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All that history and culture got you feeling famished? Stave off hunger and get your fill of retail therapy at Reading Terminal Market. A huge enclosed market located in an old train station, Reading Terminal Market has a wide array of shops, market stalls, food vendors, and places to sit back and enjoy some delicious cuisine—maybe even a Philly Cheesesteak!

Cold Spring, NY

Recommended for hiking & small-town vibes

1 hour and 20 minutes

Want to get out of the city and explore a quaint, picturesque upstate village? Take a journey one hour and 20 minutes north until you reach Cold Spring, NY. Located in the gorgeous Hudson Valley, Cold Spring is a highly popular village in Philipstown.

Cold Spring, NY

When you arrive in Cold Spring, grab your hiking boots and work up a sweat on one of the many local trails. Take in the changing seasons, wander through the woodlands, or, if you want a challenge, take on Breakneck Ridge. It’s a tricky scramble to the top, but you’ll be rewarded with expansive views across the Hudson Valley.

After you’ve exerted yourself on the trails, refuel at one of the many quaint, independent cafes and restaurants along Cold Spring’s adorable Main Street. Enjoy some fresh, delicious cuisine before browsing the vintage and specialty stores along the beautiful, well-kept streets.

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Finish off your day in the Hudson Valley by strolling by the Cold Spring waterfront. Immerse yourself in the tranquility and serenity of the water lapping against the shoreline. Sit quietly for a while before heading back to the big city.

Beacon, NY

Recommended for art lovers

1 hour and 30 minutes

If you consider yourself artsy, the ideal side trip from New York has to be Beacon, NY. Located an hour and a half north of the city, this small town has a powerful reputation when it comes to art.

Main Street Beacon, NY

Following the winding and beautiful Hudson River, a day out in Beacon is all about the galleries. Home to a plethora of contemporary art galleries—including Dia: Beacon, one of the largest in the country—Beacon is an art lovers’ paradise. Wander the hallways of the various galleries, quietly pausing to appreciate the artistry. Find a new favorite or reconnect with a piece that you love.

Once you’ve had your fill of inspiration, get out your wallet and head to Main Street. In addition to all the great boutiques, cafes, and restaurants you can refuel in, you can also browse even more art galleries where you can take a piece of this artsy town home with you.

Looking to find more of a bargain? Beacon’s Flea Market is an untapped Aladdin’s cave of wonders and curios. It’s sure to entice and intrigue any bargain hunter or thrifter with a keen eye and a sense of adventure.

Sleepy Hollow, NY

Recommended for book lovers & fall colors

1 hour

Got a bit of a spooky side? Then you’ll probably already know all about this next spin-tingling New York City side trip. Under an hour’s drive north of the city is the creepy but charming town of Sleepy Hollow, NY. The town was made famous by Irving Washington’s book of the same name. If you’re visiting New York in the fall or around Halloween, a visit to Sleepy Hollow is a must!

Sleepy Hollow, NY

Start your visit at the opulent Kykuit Estate, home to the multi-billion dollar Rockefeller family back in the 20th century. Stroll around the manicured grounds, snoop around the lavish rooms and apartments, or gaze at the many sculptures dotted around the place.

Next up, keep the Rockefeller theme going with a visit to Rockefeller State Park Preserve. Hike, bike, or paddle through this varied preserve that includes fields, streams, woodlands, and even trails made from old carriage roads. Take a moment to pause and enjoy the beauty of the Hudson Valley.

Want to get your spook on? Pay homage to Irving Washington and the supernatural vibes of the town by jumping on a Sleepy Hollow Cemetery tour. Not for the faint of heart and not exactly kid-friendly, this tour will make even the staunchest non-believers check under their beds by the end of the night!

Poughkeepsie, NY

Recommended for U.S. history buffs

2 hours

Interested in US presidential history? Just shy of two hours north of New York is Poughkeepsie, the former home of Franklin D. Roosevelt. Located on the banks of the Hudson River, Poughkeepsie benefits from stunning vistas, natural elements, as well as a historical provenance.

Poughkeepsie, NY

Begin your side trip by visiting Franklin D. Roosevelt Presidential Library and Museum. Educate yourself about the 32nd President at his former home, and learn more about his upbringing, time in office, and subsequent legacy. With gorgeous grounds leading down towards the banks of the Hudson River, you can spend a whole morning exploring and gaining knowledge at this stunning tourist attraction.

Want to enjoy the finest views of Poughkeepsie and the Hudson River? Stick on your sneakers and start strolling across the Walkway Over the Hudson State Historic Park. This historic and impressive feat of engineering welcomes over half a million visitors every year. It’s a crucial part of the larger Empire State Trail.

Whether you want to stop by and take a photo of the uninterrupted views, stand and take a moment to appreciate them, or bring your hiking boots and trek the longer trail, the Walkway Over the Hudson State Historic Park is a key stop on your Poughkeepsie adventure.

Phoenicia, NY

Recommended for white-water rafting in a quaint town 

2 hours and 30 minutes

Seeking out a distinctly small-town vibe to escape to? Grab your friends or family and drive up for some outdoorsy fun in the popular hamlet of Phoenicia, NY, just two and a half hours from New York City.

Phoenicia, NY

Located in the heart of the iconic Catskills Mountains, Phoenicia is otherwise known as the Tubing Capital of the World. With a moniker like that, your first port of call has to be the banks of Esopus Creek. Although they’re not the warmest waters in the world, the class two whitewater rapids are built for adrenaline junkies. Rush and fly over up to three-foot waves as you cascade down the creek, screaming and whooping the entire way.

Once you’ve dried off and your heart rate has come back down, head towards the main drag of Phoenicia to gorge yourself at one of the many fine dining establishments lining the quaint streets. Sit and take in the quiet hamlet around you, relax, and enjoy the small-town vibes before journeying back to NYC.

New Haven, CT

Recommended for classic college-town vibes

2 hours

Got a hankering to check out one of the world’s most famous universities? Jump in your car and drive just under two hours to the stunning coastal city of New Haven. Located in neighboring Connecticut, the crown jewel of New Haven is the prestigious Yale University campus.

New Haven, CT

Founded in 1701, Yale University is a great place to start your New Haven adventure. The Yale campus is home to historic museums, galleries, libraries, and parkland, all of which you can normally visit and wander around—even when the university is in term time. The area is home to the Yale Peabody Museum of Natural History, the Yale Center for British Art, and the Yale University Art Gallery. You can easily spend days exploring the campus alone! 

Getting hungry? Treat your tastebuds to one of the 56 Zagat-rated restaurants spread across New Haven, the most in the entire state!

Finish off your day exploring the top tourist attractions in New Haven by heading back to the Yale campus for a game or two. Catch a Bulldogs football game to see the whole city burst into life, with tailgating, parties, celebrations, and an awful lot of face paint!

Mohonk Preserve, NY

Recommended for epic hiking

2 hours

Need to stretch your legs and get out of the city? Pack all your hiking essentials and drive north for two hours until you reach Mohonk Preserve. Located just outside the quirky town of New Paltz, Mohonk Preserve offers some of the finest hikes in the area.

Mohonk Preserve, NY

This protected area spans 75 miles and includes forests, cliffs, fields, and carriage trails, offering a wide variety of terrains and trail styles. Start at the Mohonk Preserve Testimonial Gateway, pay your $15 entrance fee, and begin your day of hiking and nature exploration.

With trails ranging from highly accessible, even suitable for strollers, to pro-level difficulty, you can have your pick of exertion.

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The crowning jewel of the preserve? The Labyrinth and Lemon Squeeze hike. Despite only being a 5.5-mile loop hike, the route includes steep inclines and a rickety ladder, leading out to panoramic views across upstate New York. It’s definitely not for beginners or the faint of heart!

Fire Island, NY

Recommended for a NYC beach day

2 hours

Want to enjoy some fun in the sun? Grab your friends and family, pack up some supplies, and enjoy a fun-filled day at the beach at Fire Island. Located on Long Island, just under 2 hours from New York, Fire Island is a popular spot among locals and tourists alike.

Fire Island, NY

The best part? Fire Island is completely car-free, so you can relax, undisturbed by car horns, petrol fumes, or the nightmare of trying to find a parking spot. Instead, enjoy a relaxing train ride from Manhattan to either Sayville, Bay Shore, or Patchogue, and glide across on the ferry to Fire Island.

Once on the island, choose from one of the 18 communities to settle down in. All offer a different vibe and their own beaches. Whatever you’re looking for out of a day trip to the coast, you can find it on Fire Island.

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Fire Island spans 32 miles of coastline and features beautiful restaurants, beach bars, galleries, and boutiques. You’ll feel like you’re a million miles from the city rather than just a couple of hours!


Ryan O'Rourke is a seasoned traveler and the founder & editor of Treksplorer, a fiercely independent guide to mid-range luxury travel for busy people. With over 20 years of extensive travel experience, Ryan has journeyed through over 50 countries, uncovering hidden gems and sharing firsthand, unsponsored insights on what to see & do and where to eat, drink & stay. Backed by his travel experience and in-depth research, Ryan’s travel advice and writing has been featured in publications like the Huffington Post and Matador Network. You can connect with Ryan on Twitter/X at @rtorourke.

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