If you love American history, Philadelphia and Boston are two of the best cities in the country to visit. Both have plenty of historic sites and buildings dating back to the colonial days, each with a unique story to share. Additionally, the drive between the two takes you through some fascinating parts of the country. When you're ready to explore the history and adventures to be found between these two stalwarts of the Northeast, all you need to do is pack up your rental car and head out on this road trip from Philadelphia to New York, New Haven, Hartford and finally to Boston. Be prepared for the open road by visiting our checklist of road trip essentials.
Drive Time from Philadelphia to Boston: approximately 5 hours 20 min
Distance from Philadelphia to Boston: approximately 310 miles
Best car for this road trip: Standard SUV
As one of the original capitals of the country, Philadelphia played a crucial role in the American Revolution. If you want to explore more of these famous sites and walk in the footsteps of some of the country's Founding Fathers, you'll discover plenty of opportunities. Along with famous attractions like Independence Hall and the Liberty Bell, Philadelphia is also home to the Betsy Ross House. This small home is thought to be the place where Ross sewed the first American flag. It's now a museum dedicated to Ross' life and the history of the flag.
Another iconic destination in Philadelphia is a park located in the heart of the city. Although it's officially called the John F. Kennedy Plaza, most people know it as "Love Park." It gets this nickname because it's home to Robert Indiana's famous "LOVE Sculpture." The plaza also has the Ellen Phillips Samuel Memorial Fountain, which makes a great backdrop for a few memorable pictures. During your visit to the park, take a seat on one of the benches to enjoy a view of the city.
Selfie with the Liberty Bell, check. A photo in front of the LOVE sculpture, check. Climb the Philadelphia Museum of Art steps a la Rocky, check. It's time to begin your road trip to Boston. Get an early start to make this a one-day trip while still stopping along the way to see the sights and sounds of the Northeast. On your way out of town, stop by Philly Style Bagels. They boil their bagels in a beer solution to add malty sweetness before baking. Add some salmon lox, and you've got a breakfast of champions.
You'll start by heading north on the New Jersey Turnpike for about an hour and 45 minutes and 96 miles to reach New York City. New York offers such an incredible variety of things to see and do; the hard part is narrowing down your options.
While many people will automatically head to the Empire State Building to get a view of the city, we recommend checking out the Top of the Rock, which is an observation deck at Rockefeller Center. Not only will you enjoy sweeping views of the entire city from the 67th, 69th, and 70th floors, but you'll also get to include the Empire State Building in your panoramic picture.
If driving through the city seems a little daunting, consider stopping in the Bronx as opposed to going through Manhattan. The world-famous Bronx Zoo is an excellent stop along with the Italian markets that line Arthur Avenue.
While you could spend a lifetime exploring New York, you'll want to continue your journey. Take Interstate 95 north for around two hours and 80 miles to reach New Haven, Connecticut. If you're searching for a spot to get out and stretch your legs in this charming coastal city, head to West Rock Ridge State Park. While you're there, you can hike up to the South Overlook to enjoy incredible views of New Haven, the harbor, and even Long Island. Along with 21 miles of other hiking trails, the park also offers opportunities for rock climbing, fishing, and bicycling.
Depending on how fast you’ve sped through the morning, New Haven could be a perfect spot for lunch. You might be tempted to stop in New York City for pizza, after all, it’s some of the best. But, if you hold out until New Haven, you’ll have a chance to swing by the world-famous Frank Pepe Pizzeria Napoletana. Their white clam pizza is considered top-notch for any pizza enthusiast.
Lighthouse Point Park is another great destination in New Haven to enjoy some scenic views. Although the light in the New Haven Lighthouse no longer shines, the white, octagonal tower still stands, and it offers several great photo opportunities. The park also has an antique carousel, picnic pavilions, and hiking trails. When the weather is warm, you can cool off at the splash pad or go for a swim at the beach.
Take Interstate 91 north for around 40 minutes and 38 miles to reach Hartford, Connecticut. The state capital has several historic attractions worth seeing. One of the most popular spots is the Mark Twain House and Museum. This beautiful home is where Twain and his family lived from 1874 to 1891, and where he wrote some of his most famous pieces, including "The Adventures of Tom Sawyer" and "A Connecticut Yankee in King Arthur's Court."
While you're visiting the Mark Twain House and Museum, plan some time to head next door to explore the Harriet Beecher Stowe Center. Stowe lived in this cottage-style house for 23 years. Along with her work as a lecturer, Stowe also wrote "Pogunuc People" while she was living in the house. As you take a tour of the home, you'll learn more about her life as an author and abolitionist.
After you've finished your tour of Hartford, it's time to complete the last part of your road trip. Take Interstate 84 and Interstate 90 east for around an hour and 40 minutes and 101 miles to reach Boston. As one of the oldest cities in the country, Boston also played a vital role in the American Revolution. The best way to learn more about this is by taking a walk on the Freedom Trail.
This 2.5-mile route takes you to 16 historically significant sites throughout the city. Popular spots include Paul Revere House and the Bunker Hill Monument. While the Freedom Trail Foundation offers daily tours on the trail, you can also use the app or map to complete the tour on your own time.
You’ll need to grab a meal while hopping around the city. BBQ is not something you usually think of in New England, but Top Chef Alum Tiffani Faison is serving up some first-rate meats at Sweet Cheeks Q. From pork belly and buttermilk fried chicken to pulled pork and beef brisket, you'll satiate the inner carnivore after a filling lunch or dinner at this hot spot.
The drive between Philadelphia and Boston is rich with historical significance. Don't rush through it if you don't have to though. Consider extending your road trip into a multi-day trek filled to the brim with adventures, insights, and incredible experiences.