Here's a sample itinerary for a drive from Portland (Maine) to New York City. If you're planning a road trip to New York City, you can research locations to stop along the way. Make sure you check road conditions to double check the weather. Traveling with a dog or cat? Find pet-friendly stops. Camping along the way? Search for RV campgrounds. Find the best hotels, restaurants, and attractions based on the most talked about places recommended by Trippy members.
10:00 am start in Portland (Maine)
drive for about 2 hours
5:00 pm Old Sturbridge Village (Massachusetts)
stay overnight and leave the next day around 10:00 am
day 1 driving ≈ 3 hours
10:00 am leave from Old Sturbridge Village (Massachusetts)
drive for about 54 minutes
10:54 am Hartford
stay for about 1 hour
and leave at 11:54 am
drive for about 3 hours
2:41 pm New Jersey
stay for about 1 hour
and leave at 3:41 pm
drive for about 56 minutes
day 2 driving ≈ 4.5 hours
Boston (226 answers)
Faneuil Hall (30 mentions)
Freedom Trail (29 mentions)
Fenway Park (26 mentions)
Harvard Square (18 mentions)
Harvard University (17 mentions)
restaurants around Boston:
Legal Sea Foods
Island Creek Oyster Bar
Alden & Harlow
questions about Boston:
Best way to get to downtown Boston from Logan Airport
Is the Boston Freedom Trail worth a visit?
Worried about Boston cold weather. What should I wear?
Where are the best shopping deals in Boston?
What are the can't miss things to do in Boston?
Old Sturbridge Village (Massachusetts) (4 mentions)
Hartford (14 answers)
The Mark Twain House & Museum (4 mentions)
Wadsworth Atheneum Museum of Art (2 mentions)
questions about Hartford:
What is your favorite restaurant in Hartford?
New Jersey (27 mentions)
questions about New Jersey:
Best beach towns in New Jersey?
Best family beach town in New Jersey?
Restaurants in the East Rutherford area
Are you going straight to a hotel, or looking for a vacation rental or Airbnb?
The best resource on neighborhoods, areas, and hotels is the Trippy page on where to stay in New York City.
You can also see most people recommend as the best amount of time to visit. Find out how many days in New York City to stay.
If you're looking for a quick answer, you can check out The Standard New York, which was mentioned 15 times on Trippy.
Here are some more hotels people talk about:
Want to research more popular hotels in New York City? Click the blue button below.
Need some recommendations on somewhere to get food?
Trippy members suggest Katz's Delicatessen, which was mentioned 37 times.
Here are some more restaurants people talk about:
Want to research more popular restaurants in New York City? Click the blue button below.
This section could be endless, so rather than trying to suggest every local activity or attraction, we'll leave it open-ended.
These are some of the places people talk about on Trippy:
Of course, Trippy is the perfect place to ask questions because there's an entire community of travelers talking to each other and sharing tips and advice. Trippy is where you can get answers personalized for your tastes, budgets, trip dates & more!
Click the button below to explore more questions and answers related to New York City.
Yes, even this step is optional, because if you're on vacation who wants the trip to end? It's okay, you can start planning your next trip!
Don't forget about exploring your own hometown with a staycation. You can also find some cool day trips or get away for a weekend. Maybe try typing in a faraway location like London, Hong Kong, or Sydney, and get inspired for your dream trip around the world.
And if you know Portland (Maine) well, please help your fellow travelers and answer their questions about Portland (Maine)!