
The Best New York Road Trip : Starting in NYC

Contrary to popular belief, New York is SO MUCH more than just New York City. Just two hours north of NYC, there is TONS of hiking, kayaking, skiing/snowboarding, and so much more. New York is also pretty close to other fun cities, such as, Boston, Philadelphia, Washington D.C. the Hamptons, and more. In this article, you will read about the best New York road trip starting in NYC.
Also, in this post, you will learn about New York road trip itinerary, New York road trip stops, New York road trips upstate, New York road trip planner, the best places for road trips in New York, the Catskill Mountains, the Pocono Mountains, Finger Lakes, Niagara Falls, Hudson Valley, and much more in this article.
This article is all about a New York road trip.
New York Road Trip:
New York Road Trip : The Hamptons & Montauk
Montauk is on the tip of Long Island and is about two and a half hours away from the city (driving). You can take the train into the Hamptons and get to Montauk that way as well. As far as the Hamptons, the Hamptons are the entire area that make up the end of Long Island, while Montauk is a specific beach in the Hamptons. This is a great weekend trip or 3 day road trip from New York City to take to in the summer. There are a ton of fun beaches and places to go out to as well, that you can find here.
New York Road Trip : Cape May
Okay, onto another beach destination, Cape May. Cape May is actually located in New Jersey on the Jersey shore. However, it is the “nicer” part of the Jersey shore. It is again about a two and a half hour drive from NYC. However, Cape May is south whereas the Hamptons, are to the east of NYC. This is another great 3 day road trip from NYC or outside of the city, to take in the summer, if you have a car. As there is no public transportation from the city to Cape May. Here are some great things to do in Cape May if you decide to go.




New York Road Trip : Pocono Mountains
The Pocono Mountains are a little over an hour and a half away from NYC by car. And only a little over 2 hours from Long Island (depending on where you are driving from). The Poconos are located in Pennsylvania and there are many different towns you can stay in at the Poconos. However, I think Lake Harmony is the best. Some of the major towns in the Poconos are Blakeslee, Stroudsburg, and Split Rock. Lake Harmony is in the the southwestern part of the Poconos. There are two nice ski resorts nearby, Big Boulder and Jack Frost. Also, there’s a couple different state parks nearby, Jim Thorpe, Hickory Run, and LeHigh Gorge State Parks. In addition, the Tannerville Outlets are close-by.
Some other great Poconos Resorts to ski at are Ski Big Bear is which is farther north. Bear Creek Mountain Resort, southern part of the Poconos, close to Breinigsville and Allentown, PA. In addition there is Elk Mountain Ski Resort, another northern resort, closer to Honesdale, PA. Lastly, Montage Mountain Resorts is near the middle of the Poconos, closer to Scranton, PA. I will say, all these ski mountains are SMALL and have under 50 trails. So, I would only go here if you and family/friends are beginner skiers/snowboarders. Otherwise, you will get bored.
In the summertime, during late May to late September, the best things to are hiking, mountain biking, paint balling, adventure courses, mountain coasters, jet skiing, paddle-boarding, kayaking, and golf. A lot of these same activities are offered in the fall time as well. Also, apple picking and halloween activities are fun in the Fall time. Some other fun winter activities in the area are snowmobiling, indoor water parks (Great Wolf Lodge & H2O), tubbing, and ice skating.




{Related Post : Everything You Need to Know About the Pocono Mountains}
New York Road Trip : Hudson Valley, Beacon & Tarrytown
Now, we will switch to the best New York road trips in upstate New York. And there are plenty of options in upstate New York! Also, if you want to explore the Hudson Valley region or the town of Beacon and Tarrytown, you can take a train down if you don’t have a car. So, it’s much more convenient than some of the other road trips mentioned above. Thus, these are good towns to go to for a weekend trip. Now, there are a couple different towns and areas that make up the Hudson Valley region. The major ones are Poughkeepsie/Newburgh, Beacon, Tarrytown, Sleepy Hollow, Nyack, Cold Spring, Kingston, Hudson, Rhinebeck, Saugerties, the Catskill Mountains, New Paltz, and Woodstock.
There are more regions that make up the Hudson Valley area, however, the towns listed above are already small towns and the other towns not on this list are even smaller. The ones mentioned above have a downtown area and things to do verses the ones not mentioned. Any of the cities listed above make nice day trips or weekend trips and MOST cities are accessible via train. There’s also lots of hiking and bike trails located nearby.
Beacon is a popular town for day trips for people who live in NYC. It’s very easy, all you do is take the Metro North train into Beacon station. People like to come here for the day or weekend, and explore the shops in downtown Beacon, as well as, hike Beacon Mountain Fire Tower. In addition, the Hudson Highlands near Beacon, have great hiking too. Also, Tarrytown is a very popular and easy day trip, again, via Metro North. Poughkeepsie/Newburgh, Beacon, Tarrytown, Sleepy Hollow, Nyack, and Cold Spring are all about an hour and a half from the city. While the other cities listed above are about 2 – 2 1/2 hours away from the city.




{Related Post : Everything You Need to Know About Minnewaska State Park & A Complete Hiking Guide to the Catskill Mountains}
New York Road Trip : The Catskill Mountains & Woodstock
Another region in upstate or the Hudson Valley area, are the Catskill Mountains. The Catskill Mountains have good hiking and skiing, and a great small town to stay in. Woodstock is a great, small, artsy town to stay in, in the Catskill Mountains. They have a lot of fun farmers markets, film festivals, hiking, skiing, and snowboarding nearby.
Belleayre is a great little ski mountain in the Catskills. Windham is also nice. However, I do NOT recommend Hunter ski mountain. Hunter is filled with people that don’t know what they’re doing and usually doesn’t have good snow coverage. Which is why I recommend going to either Belleayre or Windham. Another close by city to Woodstock is, New Paltz. It also is a nice artsy small town. It has a really nice state park nearby, Minnewaska State Park, which has a lot of nice hiking and mountain biking. In addition, the Mohonk Mountain House is a beautiful place to hike at and stay at as well.
New York Road Trip : Adirondack Mountains & Lake Placid
Lake Placid is located in upstate New York, in the Adirondack Mountains. It is North of the capital, Albany. If you’re coming from NYC or Long Island, you are going to get on 87 North and literally take this, the whole way up, for about 5-6 hours, depending on traffic. If you are coming from Montreal, it’s also very simple, you will cross customs, then get on Interstate 87 South, and stay on here for about 30 miles, then you will have to go on some backroads. From Montreal, Lake Placid is a little over a two hour drive.
Since this is such a long drive (if coming from NYC or Long Island) I would make this at least a 5 day road trip from New York, maybe 7 days, if you really like the outdoors. Meaning, I would take at least 5-7 days off and dedicate 2 of those days for driving/travel days.
Okay, so once you are in Lake Placid, I HIGHLY suggest doing some hiking! There are FANTASTIC hikes located near Lake Placid, specifically in Keene Valley, which is about fifteen minutes away from Placid. The 46er challenge is located mostly in Keene Valley, and offers SPECTACULAR hikes! Seriously, hiking here, takes you to another world, I love it and HIGLY recommend it! However, be careful, because hiking in Keene Valley and Lake Placid (Adk Lodge) are no joke. If a trail is listed as difficult or advanced on AllTrails, they are NOT joking. If you are not in hiking shape, you don’t have the proper gear, and or have never hiked before, PLEASE only do a beginner to moderate rated hike. This article is a great guide to find which hikes are best for you.
Whiteface is a popular hike to climb however, if you’re not feeling up to it, you can drive all the way up to Whiteface’s summit and see the INCREDIBLE views for yourself. Once you park, you will have to walk .5-1 mile to the actual summit, or wait in line for the elevator to take you up. Also, you could go to the Flume Fall to see some amazing waterfalls.
Other Things to Do in the Adirondack Mountains & Lake Placid
In addition, Lake Placid and the Adirondack Mountains make a great winter getaway as well. They have really fun skiing or snowboarding, at Whiteface Mountain, Gore Mountain, and or Titus. Also, Lake Placid has great backcountry skiing, specifically at the Adk Lodge. This article will tell you where to backcountry ski within the Adirondacks.
In the winter time, located in downtown Lake Placid, the town offers a lot of fun activities. I HIGHLY recommend taking one or two, or ten rides on the toboggan chute on Mirror Lake. Mirror lake is located right next to the town of Lake Placid. Or you could go on a dog sled ride, also located on Mirror lake, they’re a lot of fun. Here is a link to the dog sleigh rides.




{Related Post : Complete Guide to the Adirondack Mountains & How to Spend a Weekend in Lake Placid}
New York Road Trip : Niagara Falls & Letchworth State Park
Now moving on to central and western New York, some notable towns in central New York to visit are Cooperstown, Syracuse, and Ithaca. And in western New York, some fun towns to visit are Buffalo (Niagara Falls), Rochester, and the finger lake region. Again, this is a New York road trip 7 days that I would spend getting to Buffalo/Niagara Falls. From NYC and Long Island to get to the towns listed above, it will be about a 6-7 hour drive. You can find directions here.
If you want to see Niagara Falls, I would stay in Buffalo. The falls are only about 30 minutes from Buffalo and you could also visit Letchworth State Park and do some hiking (about an hour southeast of Buffalo). Here are some other fun hikes and skis mountains in Buffalo, NY. In addition, if you visit Buffalo/Niagara Falls, you could take a quick day trip to either Niagara on the Lake (in Canada) or Toronto, Ontario, Canada.
- Niagara Falls State Park : near Buffalo, NY, beginner to intermediate hikes.
Letchworth State Park : Castile, NY, beginner to intermediate hikes (Eternal Flame Falls & Grimes Glen). - Chimney Bluffs State Park : Buffalo, NY, beginner to intermediate hikes.
- Niagara Falls State Park : near Buffalo, NY, beginner to intermediate hikes.
- Watkins Glen State Park : Schulyer County (close to Ithaca), NY, beginner to intermediate hikes.
- Finger Lakes National Forest : Hector, NY, beginner to intermediate hikes.
- Akron Falls Park : Buffalo, NY, beginner hikes.
- Bristol Mountain for skiing and snowboarding: Bristol, NY.
- Holiday Valley Resort : Ellicottville, NY
- Holimont : Ellicottville, NY
- Song Mountain : Tully, NY
- Swain Mountain : Swain, NY
New York Road Trip : Finger Lakes, Crystal Beach & Watkins Glen
The Finger Lake region is only about an hour away from Ithaca, which I suggest staying at if you are interested in hiking this area. Also, Ithaca and the Finger Lakes offer great wine tours if you want a break from hiking. There are many great places to hike and great waterfalls to see. The Finger Lake Region and Ithaca, NY are about a 4-5 hour drive from NYC and Long Island.
This would be best for New York road trip in 4 days. Here are directions. Here are some fun wine tours to take while visiting. Listed below are some more fun things to do in or near the Finger Lakes Region.
- Fillmore Glen State Park : near Ithaca, NY, beginner to intermediate hikes.
- Watkins Glen : about 40 minutes from Ithaca, NY, nice beginner walking trails.
- Crystal Beach : in Canandaigua, NY, about an hour and a half from Ithaca.
- Biking : Ithaca, NY.
- Horse-back riding : Ithaca, NY.
- Cross-country skiing & snow-shoeing : Ithaca, NY.
- Greek Peak skiing and snowboarding : about 30 minutes from Ithaca, NY.




{Related Post : Where to Find the Best Hiking in New York}
And that wraps up our article about New York road trips! I hope you learned about new New York road trip stops, New York road trip ideas, and more places to travel to in general. Some other fun cities that you can take a train to from NYC are Boston (about 5 hours via train), Washington D.C. (about 3 & 1/2 hours via train), and Philadelphia (about 2 hours via train). Thank you so much for reading and take care!