Here's a sample itinerary for a drive from Stamford (Connecticut) to Boston. If you're planning a road trip to Boston, you can research locations to stop along the way. Find the best hotels, restaurants, and attractions based on the most talked about places recommended by Trippy members.
10:00 am start in Stamford (Connecticut)
drive for about 47 minutes
10:47 am New Haven
stay for about 1 hour and leave at 11:47 am
drive for about 42 minutes
12:29 pm Hartford
stay for about 1 hour and leave at 1:29 pm
drive for about 58 minutes
2:27 pm Old Sturbridge Village
stay for about 1 hour and leave at 3:27 pm
drive for about 47 minutes
4:13 pm Milford (Massachusetts)
stay for about 1 hour and leave at 5:13 pm
drive for about 41 minutes
5:55 pm North End
stay for about 1 hour and leave at 6:55 pm
drive for about 5 minutes
driving ≈ 4 hours
Your starting point is Stamford, Connecticut.
You can enter an exact street address if you want to get precise directions, but this is optional.
Since there are only 2 travelers, we assume you're driving 1 car. You can adjust the number of people traveling at the top. We assume a maximum of 4 passengers per car, but you can change the number of cars to fit your situation.
New Haven (8 answers)
restaurants around New Haven:
Frank Pepe Pizzeria Napoletana
questions about New Haven:
What's the best neighborhood in New Haven for a first time visitor?
Let's get serious about Pizza..... Sally's? Pepes? or Modern?
Hartford (10 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?
Old Sturbridge Village (4 mentions)
questions about Milford (Massachusetts):
North End (39 mentions)
Your final destination is Boston, Massachusetts.
You can enter the exact street address of your destination, but this is optional.
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 Boston.
You can also see most people recommend as the best amount of time to visit. Find out how many days in Boston to stay.
If you're looking for a quick answer, you can check out The Westin Copley Place, which was mentioned 4 times on Trippy.
Here are some more hotels people talk about:
Want to research more popular hotels in Boston? Click the blue button below.
Need some recommendations on somewhere to get food?
Trippy members suggest Mike's Pastry, which was mentioned 15 times.
Here are some more restaurants people talk about:
Want to research more popular restaurants in Boston? 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 Boston.
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 Stamford (Connecticut) well, please help your fellow travelers and answer their questions about Stamford (Connecticut)!