The drive from New York to Boston is often done by business professionals, but more and more people are discovering the beauty and enjoyment this short road trip offers. This drive is particularly beautiful during the fall months when red, yellow and brown foliage turns highways into remarkable landscapes reminiscent of paintings from the Hudson River School art movement. To fully appreciate the beauty of the single-day trip, try to avoid taking these highways during peak commute hours – early morning and late evening – to ensure a smooth and enjoyable drive. Be prepared for the open road by visiting our checklist of road trip essentials.
New York City is one of the most visited cities in the world. While it attracts business professionals and artists chasing the American Dream, the streets are packed with visitors trying to get on a tour to see the Statue of Liberty, catch a glimpse of the Empire State Building or wander around Time Square. During your time in the city, consider stopping in for a stage performance on or off Broadway. Some of the shows do require advanced tickets, so plan accordingly. Some of the best performers and performances can be found in this city, making it a must-see for art fans.
You’ll want to grab some food in the City That Never Sleeps before you head out on the trip. A stop into the century-old Russ and Daughters will score you an iconic New York bagel with schmear and smoked salmon. Breakfast doesn’t get any better.
Driving through Manhattan can be daunting, so you may want to pick up your rental car closer to the Bronx where you can easily hop on I-95 and head to Boston.
Depending on the traffic, it should take two to three hours to reach New Haven, CT from Manhattan. While the journey is only 80 miles, this stretch of highway is notorious for heavy traffic in peak hours, which is why New Haven is a great place to take a pit stop. Interstate 95 will take you directly to the city along the Long Island Sound.
New Haven is home to Yale University. Venture onto campus and walk the same steps as Bob Woodward, Bill Clinton, Clarence Thomas or even notable fictional characters such as Rory Gilmore and Nick Carraway. Stretch your legs as you walk along campus and relax in the courtyards and greens created by the University.
There will be plenty of affordable food options located near or around campus. A notable lunch is to get the famous white clam pizza from Frank Pepe’s pizzeria, often regarded as the best or one of the best pizza’s in the entire country.
Once you’ve graduated from your short time at Yale, deviate from I-95 to I-91 and head to Hartford, the Connecticut state capital. The city is roughly 40 miles away, and the trip should take 40 minutes to an hour to complete. Literary fans will want to stop at the Mark Twain House, to see where Tom Sawyer and Huckleberry Finn were created followed by a jaunt over to the Harriet Beecher Stowe Center. Even if you just use your time to wander around to state capitol, it will be time well spent.
The final stretch of road between Hartford and Boston can last up to two hours during peak driving hours as road travelers complete the final 100-mile stretch to their destination. Take I-84 until you enter Massachusetts and switch over to I-90 into the city.
Boston is known for its sports, food and American history. A visit to historic Fenway Park to see the Boston Red Sox play is essential, even if you're a Yankees fan, although wear your team’s gear at your own risk. Visitors can enjoy hot crocks of clam chowder or freshly prepared lobster. Just make sure you save room after dinner for some Boston cream pie when you're done.
If you make it into the city before the dinner hour, grab an afternoon sweet treat from Flour Bakery + Café to tide you over. Their sticky buns will pleasantly haunt your dreams for the rest of eternity.
History buffs will enjoy The Freedom Trail, a 2.5-mile-long path through downtown. Visitors who walk this path can stop and enjoy 16 historic sites, easily spending an entire day learning about the events that made America the country it is today.
Driving around New England is blissful during the fall, but is also plenty exciting during other seasons. Many visitors take this trip in the summer when the temperature is warm but not brutally hot. Feel free to stop in other towns and parks along the way for picnics or just to walk around and enjoy the fresh country air in between the densely populated New York and Boston metro areas.
What can you do for free in NYC?
Some people may think of New York City as an expensive place to visit, but there are plenty of free attractions to see, including:
What is there to see in New Haven?
New Haven has a variety of fun things to do, so you're sure to find one you enjoy. Check out the following places:
What is Boston best known for?
Boston is famous for a things like Harvard University, the Boston Marathon, and baked beans. Well-known attractions include Fenway Park, Cape Cod, and the bar featured in the TV show Cheers.