10 Best Weekend Trips from Long Island by Car

Jordan Hinsch

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As a native Long Islander, I wish I did more of these trips while I still lived there. I know how boring Long Island can get and a change of scenery every now and then is very important.

Here are some ideas for a fun weekend getaway from Long Island.

NOTE: I've included a Covid-19 rating which is scored from 1-10, 10 being the best. This is my personal opinion of how they're handling the pandemic in terms of mask requirements, openings, and what I think your potential risk is. A city which is open but has very relaxed mask requirements will score low, whereas a city which is not open and has very strict mask requirements will also score low. You should be looking for the perfect medium since I'm sure you don't want to embark on a weekend getaway and have nothing to do, but you also want to feel safe.

The Poconos, Pennsylvania

Why? The Poconos are a massive area situated in the Appalachian Mountains in Pennsylvania and serve as a popular weekend getaway for New Yorkers. It is best known for skiing/snowboarding in the winter and great whitewater rafting in the summer. Camelback is the most popular ski resort.

  • Drive Time: 2-2.5 hours each way
  • Tolls: Yes
  • Covid-19 Rating: 7/10
  • Hotel Recommendation: None. Get an Airbnb or VRBO in the mountains!
  • Where to Eat: Moya for a first class variety of international cuisine.
  • See other hotels and restaurants in The Poconos

Hunter Mountain, New York

Why? Hunter Mountain is primarily known for it's slopes in the winter and summer festivals. It's usually referred to as the best place to ski or snowboard on the east coast.

  • Drive Time: 3 hours each way
  • Tolls: Yes
  • Covid-19 Rating: 7/10
  • Hotel Recommendation: None. Get an Airbnb or VRBO in the mountains!
  • Where to Eat: Jagerberg Beer Hall & Alpine Tavern for some great beer and German cuisine.
  • See other hotels and restaurants in Hunter Mountain

Finger Lakes, New York State

Why? The Finger Lakes are located in Western New York and are known for fishing and wineries. It serves as a nice getaway for those Long Islanders who are tired of the eastern Long Island vineyard situation!

Newport, Rhode Island

Why? Newport is located in an out-of-this-world location in Rhode Island on impressive cliffs. While there, I recommend you take the 3.5 mile Cliff Walk. It's a tourist trap, but an absolute must.

Philadelphia, Pennsylvania

Why? Home to my alma mater, Philadelphia will always have a special place in my heart. Many come to Philadelphia for the history, and there is loads to see. I recommend seeing some breweries and eating at some fun restaurants in center city.

Boston, Massachusetts

Why? A lot of New Yorkers hate Boston because of the sporting rivalries. They'd be remiss if they didn't visit Boston at least once every few years. Like Philadelphia, it's loaded with history, but Boston is a unique city in itself, and let's face it, they've had more success with fewer sports teams (it hurts me to say that as a New Yorker but it's true, debate me on that!).

  • Drive Time: 3.5 hours each way
  • Tolls: Yes
  • Covid-19 Rating: 6/10
  • Hotel Recommendation: Boston Harbor Hotel
  • Where to Eat: Neptune Oyster for the best lobster rolls in town
  • See other hotels and restaurants in Boston

Portland, Maine

Why? The first capital of Maine, Portland is home to almost 40% of the state's population. It's an oceanfront city which means the seafood is "to die for". Views, food, and culture consume this lovely area.

  • Drive Time: 2-2.5 hours each way
  • Tolls: Yes
  • Covid-19 Rating: 8/10
  • Hotel Recommendation: The Francis
  • Where to Eat: Back Bay Grill
  • See other hotels and restaurants in Portland

The Berkshires, Massachusetts

Why? The Berkshires are known for outdoors activities and culture. It's traditionally a getaway for the baby boomer population and the summer festivals usually feature well-known acts from the 60s and 70s.

  • Drive Time: 2.7 hours each way
  • Tolls: Yes
  • Covid-19 Rating: 6/10
  • Hotel Recommendation: None. Get an Airbnb or VRBO. This is also a popular timeshare location.
  • Where to Eat: Chez Nous
  • See other hotels and restaurants in The Berkshires

Cape Cod, Massachusetts

Why? Key West is traditionally known as a city where people go to party and be wild. It's still that same city, but there is great music, culture, and loads of non-alcohol related activities to partake in.

  • Drive Time: 4.5 hours each way
  • Tolls: Yes
  • Covid-19 Rating: 8/10
  • Hotel Recommendation: Lands End Inn. Very upscale, but worth it for the views and service.
  • Where to Eat: Far Land Provisions
  • See other hotels and restaurants in Cape Cod

New Paltz, New York & Poughkeepsie, New York

Why? Mostly known as college towns, New Paltz and Poughkeepsie offer great hiking and other outdoors activities along with a fun bar scene. Fun Fact: New Paltz is home to many movie stars.

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Jordan Hinsch is a sales expert, blogger, investor, photographer, videographer, and outdoors enthusiast. Primarily known for unique travel and bucket list related content, Jordan also specializes in lifestyle, fitness, and finance. Follow him here on NewsBreak and on Instagram & Pinterest @neverjordinary.

Miami, FL
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