Here's a sample itinerary for a drive from New York City to Portland (Maine). If you're planning a road trip to Portland (Maine), 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.
11:00 am start in New York City
drive for about 1.5 hours
12:36 pm New Haven
eat at Modern Apizza
stay for about 1 hour
and leave at 1:36 pm
drive for about 42 minutes
2:19 pm Hartford
stay overnight and leave the next day around 10:00 am
day 1 driving ≈ 2.5 hours
find more stops
10:00 am leave from Hartford
drive for about 1.5 hours
11:33 am Providence
eat at Trinity Brewhouse
stay for about 1 hour
and leave at 12:33 pm
drive for about 2.5 hours
2:55 pm Kennebunkport (Maine)
stay for about 1 hour
and leave at 3:55 pm
drive for about 35 minutes
4:29 pm arrive in Portland (Maine)
stay at Portland Regency Hotel & Spa
day 2 driving ≈ 4.5 hours
find more stops
Aphtyn from Durham, Maine asked:
Cheap bus lines (roundtrip) from Portland, Maine to New York, NY. (1 answer)
New Haven (10 answers)
restaurants around New Haven:
Modern Apizza
Frank Pepe Pizzeria Napoletana
Goodfellas Restaurant
questions about New Haven:
What is your favorite restaurant in New Haven?
Let's get serious about Pizza..... Sally's? Pepes? or Modern?
Hartford (15 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?
Providence (19 answers)
WaterPlace Park (2 mentions)
Thayer Street (2 mentions)
Prospect Terrace Park (2 mentions)
restaurants around Providence:
Trinity Brewhouse
North
Al Forno Restaurant
Gracie's
Ken's Ramen
questions about Providence:
What is your favorite restaurant in Providence?
What should I do/see/eat in and around Providence in 48-72 hours?
Best dinner in Providence—that also has a great atmosphere?
Best lobster spot in Providence?
Kennebunkport (Maine) (24 answers)
Wells Beach (3 mentions)
York Beach (2 mentions)
restaurants around Kennebunkport (Maine):
All Day Breakfast
questions about Kennebunkport (Maine):
family vacation
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 Portland (Maine).
If you're looking for a quick answer, you can check out Portland Regency Hotel & Spa, which was mentioned 2 times on Trippy.
Want to research more popular hotels in Portland (Maine)? Click the blue button below.
Need some recommendations on somewhere to get food?
Trippy members suggest Duckfat, which was mentioned 5 times.
Here are some more restaurants people talk about:
Want to research more popular restaurants in Portland (Maine)? 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!
For example, here are some questions people have asked about Portland (Maine). Click on any question to see answers from the community!
Andreas from Manhattan asked:
Good restaurants in Portland (5 answers)
Priscilla from Santa Monica asked:
Best places to eat in Portland, ME (4 answers)
Irene from New York State asked:
Things to do and good restaurants in Portland, ME (3 answers)
Casey from Boston asked:
Best Breakfast spots in Portland, Maine? (3 answers)
Click the button below to explore more questions and answers related to Portland (Maine).
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!
Want to plan the trip back? Get the reverse directions for a Portland (Maine) to New York City drive, or go to the main page to plan a new road trip.
You can also compare the travel time if you're flying or driving by calculating the distance from New York City to Portland (Maine). Or get a full New York City to Portland (Maine) flight plan.
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 New York City well, please help your fellow travelers and answer their questions about New York City!