The 9 Best All-Season Road Trips From New York

One of the best ways to enjoy your vacation in New York is by renting a car and driving to beautiful, historic cities and states like New Hampshire, Pennsylvania, Massachusetts, Virginia, and the Carolinas. Each is easily reached within a day’s drive, making the possibilities for exploring beyond New York in any season endless.

Below we are sharing our favorite 7-day road trips from New York as well our favorite weekend road trips, too. There are plenty of ways to enjoy the cities and states around New York, so we hope this guide to NY road trips inspires you for your next trip!

As a note before we get started, each of these suggested road trips starts and ends in New York.

Our Favorite 7-Day Road Trips From New York

  1. 01

    7-Day Road Trip From New York to Vermont and New Hampshire

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    After planning a packed visit to New York, with all its museums, restaurants, and Broadway shows, take a road trip to Vermont and New Hampshire to really enjoy one of America’s most beautiful spots. With New Hampshire about four and a half hours by car from New York and Vermont just an hour or two from New Hampshire, this is a trip that prioritizes time outside.

    Head to Bretton Woods in New Hampshire in the White Mountain National Forest for some of the region’s best snowshoeing in the winter and incredible mountain biking and hiking during the summer. Over in Vermont, the Killington Resort is one of the region’s biggest, also offering snowmobile tours, a tubing park, and more.

    Wondering when to plan your Vermont and New Hampshire road trip? It’s easy to take advantage of your preferred season. For skiing in Vermont and New Hampshire, the snowfall can start in November and often lasts until mid-April. For hiking and fishing, come in the summer. For the stunning colors of changing leaves, come in autumn. 

  2. 02

    Roadtrip from NYC to Watkins Glen and Letchworth State Parks, Niagara Falls and 1000 Islands

    Day Trip in Outside of New York City
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    We have again made a great tour from New York: The route leads once through the entire state of New York, with Niagara Falls on the northeastern border with Canada, along the beautiful Finger Lakes to the 1000 Islands on the northeastern border. You can expect a beautiful landscape with many farms, rivers and dreamlike nature.

    After this tour, which incidentally follows the course of the Erie Canal, which is largely responsible for the rise of New York City, you can also proudly claim to have been in Lebanon, Athens, Rome, London, Amsterdam, Russia and Hamburg. Because all of these places are located along this great road trip.

    The next road trip from New York on my list is quite similar but you spend more time in Canada with Toronto and Montreal on your list.

  3. 03

    7-Day Road Trip From New York to Canada

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    Did you know that New York shares a border with Canada? It can be easy to forget with all of the focus on Manhattan that New York state is actually a fairly big state – and one that connects with America’s neighbor the north.

    For a break from New York city life and to experience Canadian culture, you’ll enjoy a weeklong road trip to Canada with stops at Niagara Falls (even taking a boat underneath the falls!), Toronto (where you can size up the city with the view from the CN Tower), and Montreal (where you’ll see the French influence is still alive and well).

    Driving from New York to Niagara Falls will take just under seven hours. From there, you’ll drive for two hours to Toronto. Toronto to Montreal is about five and a half hours. Then returning to New York will take about five hours. Though chillier in the winter, this is a beautiful roadtrip from NYC to take no matter the season.

    My Tip

    This road trip from New York is also available as a guided 5-day tour. You can find out more about it here 👇

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  4. 04

    Get To Know America’s Roots on this Roadtrip from New York

    Day Trip in Outside of New York City
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    New York can feel like the most American of cities: lots of cultures, lots of opportunity, lots of, well, everything. If you want to spend some time getting to know American history, then use a weeklong road trip to head to Washington D.C. and Virginia.

    In Washington, D.C., which is about fours from Manhattan by car, you’ll find the National Mall, one of the most concentrated and impressive collections of museums in the United States. Continuing onto Virginia, which was home to four of America’s first five presidents, you can visit living-history museums like the Jamestown Settlement and Colonial Williamsburg.

    After your fill of culture and history, you can take advantage of the stunning Shenandoah Valley before taking a four-hour drive over to Virginia’s Eastern Shore to soak up the ocean sprays.

    Given this mix of city visits and natural parks, this is a trip that’s enjoyable throughout the year.

  5. 05

    Taste Southern Hospitality in South Carolina on this roadtrip from NYC

    Day Trip in Outside of New York City
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    After a few hectic days in the hustle and bustle of New York, a trip down the coast to South Carolina can be a wonderful experience. The total driving time from Manhattan down to South Carolina is about 11 hours. Spread out over six or seven days, that means you can enjoy visits to the scenic Blue Ridge Parkway in Asheville, North Carolina on your way to Hilton Head and Charleston, South Carolina.

    So-called the Birthplace of Barbecue, South Carolina is as much a culinary destination as a cultural one. Enjoy the change of pace and scenery over your weeklong road trip as you enjoy true Southern Hospitality.

    If you’re planning a winter vacation in New York, South Carolina may be a bit warmer, offering you a chance to thaw out. During the summer it can be more humid. Either way, the barbecue is always delicious and the people are always charming.

  6. 06

    Roadtrip from NYC to Boston, White Mountains, Niagara Falls and Washington D.C.

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    This tour along the East Coast is one of the most impressive road trips I have taken in the USA so far. In October 2016, my father and I started in New York – where else?! I wanted to show him why I have loved this city so much for years and which spots are close to my heart. 

    In total, this route takes you a total of 1,600 miles through 12 US states. What are our highlights of this road trip on the East Coast of the USA for us, I show you here in the travel review.

  7. 07

    History And Food In And Around Philadelphia

    Day Trip in Outside of New York City
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    If you are looking for an amazing weekend road trip adventure from New York look no further! Apart from being known for Rocky’s hometown, Philadelphia is also one of America’s most iconic and historical cities. It’s even where the signing of the Declaration of Independence happened on August 2nd, 1776! So if you’re looking to add a weekend trip onto your time in New York, Philadelphia and a few of its surrounding cities could make for a great choice.

    At just under two hours by car (and even less by train!) Philadelphia is an easy trip from New York. Along with stopping by to see the Liberty Bell at Independence Hall, you can also see the birthplace of the American flag and the Museum of the American Revolution (before taking a lunch break to grab a renowned Philly Cheesesteak).

    To make a weekend of it, it’s worth turning toward the countryside and heading toward Brandywine Valley. Filled with quaint towns and rolling hills, the region also has a number of renowned wineries making up the Brandywine Valley Wine Trail. 

    And what pairs with wine better than chocolate? Just an hour and a half by car to the west, Hershey is the birthplace of Hershey chocolate and the so-called Sweetest Place on Earth. Ideal for families, Hershey features the Hershey Story Museum, Hershey’s Chocolate World, and Hershey Gardens.

    Though there are a number of Christmastime activities that make for even sweeter seasonal celebrations, the attractions are open year-round, making Philadelphia, Brandywine, and Hershey a great weekend trip to take from New York.

    My tip: An additional stop in Washington D.C. is a great extension to this road trip from New York. Besides the White House, you can visit the Lincoln Memorial, the famous Smithsonian Museums, the United States Capitol or the Washington Monument.

  8. 08

    Hike Upstate New York: One Of The Best Weekend Road Trip Adventures From New York

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    When you want to get out of the city for a few days, hiking in upstate New York is one of the best options. No matter the time of year, hiking in the Adirondacks, the Catskills, and the surrounding regions always offers incredible views, serene nature, and charming small-town atmosphere. 

    To get to the Adirondacks from Manhattan, you’ll need about four and a half hours in a car. Perfect for a morning start and a leisurely afternoon hike. Among some of our favorite Adirondack adventures are the Ausable Chasm (which also has white-water rafting for those summer month trips), Cascade Mountain (the supposed easiest of the 46 High Peaks), Mount Marcy (the highest of the 46 High Peaks), and the Saranac Lake 6er (a delightful hiking challenge you can try and tackle in a single weekend).

    At just over two hours driving time, the Catskills are an even more accessible weekend trip from New York. With stunning waterfall hikes (don’t miss the Haines Falls!), the Hunter Mountain Fire Tower (one of the region’s most challenging hikes), and plentiful Nordic skiing and snowshoeing, there are plenty of outdoors activities to choose from.

    With well-marked trails for any season, you’ll find the snowy hikes and the summertime strolls equally enjoyable. Just make sure you’re dressed for the occasion!

  9. 09

    Go Wine Tasting In The Finger Lakes

    Day Trip in Outside of New York City
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    Want to taste some of the best wine in New York? Soak up the small-town life in some of the state’s quaintest towns? Enjoy some idyllic lakes?

    Then it’s time to head to the Finger Lakes Region. Located in upstate New York, the Finger Lakes is home to towns like Ithaca (and Cornell University, the region’s Ivy League), Watkins Glen (some of the best hiking in the area), and Geneva (recent winner of the All-America City award).

    If you’re looking to get your wine on, the Finger Lakes themselves have four official wine trails ready to be embarked on. This includes

    • the Canandaigua Lake Wine Trail
    • the Cayuga Lake Wine Trail (“America’s First Wine Trail”)
    • the Keuka Lake Wine Trail,
    • and the Seneca Lake Wine Trail.

    From Manhattan to the Finger Lakes, you can expect to spend about 5 hours in the car. Perfect for a Friday departure with a few roadside attractions, a lazy Saturday, and then a return late Sunday afternoon. With wine-tasting rooms and events all year round, the time is always right to stop by the Finger Lakes.

Which Road Trip or Day Trip from New York is the Best?

Check out my free road trip advisor that will help you choose from over 30 road trips and day trips to suit your needs!

Frequently Asked Questions About Road Trips From New York

If I rent a car, does my road trip have to end back at New York?

Nope! Most rental car agencies are flexible with the return location for your rental car. There may, however, be a slight surcharge for returning it in a different spot than you started. 

Which states make up the New England region?

This is one of the most gorgeous areas to visit during the autumn. But for those not familiar with the area, the name can be a little misleading. New England is the name given to a northeastern region of the U.S., and it includes Maine, Vermont, New Hampshire, Massachusetts, Connecticut and Rhode Island. 

What’s the best time of year to do a road trip from New York?

There’s an argument to be made for each season. New York City is the hottest during the summer, so a road trip can be a nice way to escape the heat and explore some of the amazing nature around it. If you’re planning to spend time exploring other cities, a road trip in the spring and fall will give you the most agreeable temperatures. And if you’re planning to do some winter sports, then the winter season will work best. The only risk with winter is, naturally, that a large snowstorm could make travel by road difficult. Fortunately, the region is well-prepared to handle this kind of weather and delays would likely be minimal.

About the author
Steffen

I'm a true New York fan! Not only have I visited the city over 20 times but also have I spent several months here at a time. On my blog I show you the best and most beautiful spots of the city, so that you have a really good time! You can also find lots of insider tips in our New York travel guide. Also check out my hotel finder for New York!

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