Sometime around middle school, most students in the United States will study U.S. history. This is the perfect time to plan a U.S. History road trip through the Mid-Atlantic and Northeast to visit many of the main historic sites that are so relevant to the founding of our country.
We have found through our travels that seeing a place in real life and walking in the steps of our Founding Fathers works wonders to bring history to life. There is something about learning (or relearning) the history in those places that makes everything click into place, stick in the memory better, and allows kids to see the bigger picture.
Of course, there is so much history to cover across the country, but for this itinerary, I would stick to the destinations related to our Colonial History and Revolutionary War on this northeast road trip.
Later, you can tackle other themes like a Civil Rights road trip, Trail of Tears or Oklahoma road trip, Lewis & Clark, etc.
On this US History road trip itinerary, you can squeeze everything into about two weeks, but if you have extra time you can add in some side trips and some fun stops along the way.
Northeast Road Trip Itinerary
I have started this road trip in Virginia, to explore some very early Colonial History, and worked our way up to Boston, but you can certainly take this road trip in reverse. To save time, I would recommend flying into Norfolk International Airport (Breeze Airlines offers some affordable flights into this airport.)
However, if that is too cost prohibitive, you can start in Washington D.C. and take a slightly different route. But to minimize driving and backtracking, I would suggest the following order: Williamsburg/Jamestown, Washington D.C., Baltimore, Philadelphia, New York, and Boston.
Map created with Google My Maps.
Williamsburg (2 days)
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It is approximately one hour from the Norfolk International Airport to Williamsburg. Along the way, you could always stop in historic Hampton, VA and visit the Virginia Air & Space Center or the Virginia Living Museum in Newport News. But if you have limited time and want to stay focused, head right to Williamsburg.
You can see Colonial Williamsburg in a day, but to fully enjoy it, you really want to give it two. There is so much to see and take in from troop parades to historic reenactments. You can also add on experiences like a carriage ride, ghost tour, or theater performance.
Side trip idea: If you have extra time, take a day to enjoy Busch Gardens amusement park or the Watercountry USA water park.
Where to Stay: I would recommend staying at the Woodlands Hotel & Suites in Colonial Williamsburg.
Jamestown & Yorktown (1-2 days)
Technically, if you want to follow history chronologically, you would visit Jamestown first, then Williamsburg, then Yorktown — but who needs to be fussy? Jamestown is about 15 minutes from Colonial Williamsburg and Yorktown is about 20 minutes in the other direction but if you are pressed for time, you could visit both in a day or spread them out and visit one a day, keeping your home base at the Woodlands in Williamsburg.
There are actually two sites to visit in Jamestown. There is Historic Jamestowne, which is the actual site of the original fort settled by Captain John Smith and some of the first European settlers. It is an actual archeological dig and while interesting, there is much more to see and do at Jamestown Settlement down the road. Confused? I was too so I wrote a post describing the differences between Historic Jamestowne vs. Jamestown Settlement.
Any Hamilton fan knows the importance of the Battle of Yorktown. The American Revolution Museum at Yorktown is a living history museum complete with galleries, films, and interactive exhibits. Here you can learn about the twilight of the Colonial period and the dawn of the United States. The Siege of Yorktown film tells the story of that decisive battle. Meanwhile, outdoor living history areas incorporate artillery demonstrations and drill reenactments.
It is easy to spend at least a half a day at each, so if you have the time, you may want to visit one a day and spend the afternoon relaxing.
Washington DC (3 days)
It is a two and one-half hour drive from Williamsburg up to Washington D.C.. After two family trips, we still have so much that we haven’t seen. Some of the must-dos for first-time visitors include: visiting the National Mall and Monuments (the Monuments are especially beautiful and peaceful to visit at night), Smithsonian National Museum of American History, National Museum of African American History and Culture (make sure you book tickets ahead), and the National Archives (to see the original Declaration of Independence.)
Other kid favorites include the National Air and Space Museum (and the excellent annex outside of D.C.), the Museum of Natural History (for those Night at the Museum fans), and the International Spy Museum.
Of course there is so much to see in the Capital that you could spend a week and still have more to see so don’t rush it, give yourselves at least three days in Washington D.C. Intersperse museums with bike tours through the Tidal Basin, walks through the monuments, and time playing on the National Mall.
Also keep in mind that if you want to visit the White House, you need to arrange it through your Congressman/woman at least a few months in advance and follow strict security clearances.
Where to Stay: There are many hotel options, with some of the affordable ones located just outside the city. Luckily the D.C. Metro is easy to use and an affordable way of getting around. If you do want to stay in walking distance to sites, we enjoyed our stay at The Darcy (a Curio by Hilton Property) and got a great deal!
Baltimore (1-2 days)
From Washington D.C., it is just an hour drive up to Baltimore. While there are not as many historic sites to see in Baltimore, I just love this city so much that I need to include a brief stay on this road trip itinerary. It can also make for a nice break from museums.
A visit to the National Aquarium is a must, but I’d recommend buying timed-entry tickets online in advance to save time waiting in line. You will still need at least half day at the Aquarium. Then there is so much else to do in the Inner Harbor from the Science Museum, to pedal boats, and historic ships.
You can also take a water taxi over to Fort McHenry. The defense of Fort McHenry in the Battle of Baltimore inspired Francis Scott Key to write the Star Spangled Banner.
If you have time, be sure to explore the African American history of Baltimore. Whatever you do, don’t miss breakfast at Miss Shirley’s.
Where to Stay: Twice we have stayed at the Hilton Baltimore and I love the location. It is within easy walking distance to the Inner Harbor and right behind the Camden Yards baseball park so you can hang out on the conference level floor and watch the game (or book a room overlooking the stadium.)
Philadelphia (2 days)
Every US History road trip has to include a trip to Philadelphia. What better place to soak in our early U.S. history than where the Declaration of Independence was signed and the U.S. Constitution was penned?
Start off at Independence Hall. Tour tickets should be booked in advance. Here you can be in the “room where it happened.”
I have some other tips for touring historical Philadelphia because there is so much to see and do in the City of Brotherly Love. We especially loved the National Constitution Center, which did a great job describing the challenges facing our early nation and the hard work it took to put the Constitution together. It helped explain some of the compromises the delegates made and how some decisions, like not abolishing slavery, impacted the country for decades to come (and the impacts are still felt today.)
Don’t miss the Liberty Bell, but the lines can be long in the morning, so you are better off visiting late in the day or just viewing it from outside the glass building where it is housed. Personally, I think the Betsy Ross House could be skipped, but we loved the National Museum of American Jewish History.
For lunch, walk over to the Reading Terminal Market, where you will have your choice of treats from cheesesteaks, to pretzels, and funnel cake.
Side trip ideas: If you have time, schedule a side trip to take a dip into Civil War history (which is a great follow up after visiting Philadelphia.) I would recommend a scenic drive through Pennsylvania Dutch Country and spending two of days in Gettysburg and then visit the National Civil War Museum in Harrisburg, PA. We were really blown away by how much we loved Gettysburg and how impactful it was.
But if the kids are getting antsy by this point, plan a day in Hershey, the “sweetest place on earth” and home to Hersheypark amusement park and Hershey’s Chocolate World. On the drive back east, you can stop at Valley Forge National Park and get a little more Revolutionary War history.
Where to Stay: Try to stay in the historic city center to make everything very accessible. The Kimpton Hotel Monaco Philadelphia is the perfect location. I’ve stayed here twice and really like this hotel and location.
New York (2 days)
It is only two hours from Philadelphia from New York City, not accounting for the inevitable traffic. The first choice is choosing which neighborhood to use as your home base. If you are focused on history, I would recommend staying in Lower Manhattan. Otherwise, Midtown or Times Square is a good central location.
New York can be overwhelming for visitors so I usually recommend knocking off just one or two neighborhoods per visit. From Lower Manhattan you can visit the 9/11 Memorial and enjoy some free time in Battery Park. It is also a good jumping off point for visits to the Statue of Liberty and Ellis Island (if you want to learn some more recent U.S. history and trace the immigration routes of ancestors.)
However, for history buffs, the ultimate achievement in NYC would be to score tickets to see Hamilton on Broadway. Especially since we can credit this amazing show for getting so many kids interested in this period of history.
Even if you can’t get tickets (and I hope you can, it is such an amazing show!!), you can still take a Hamilton walking tour to see Alexander Hamilton’s New York. There is more history to explore in Lower Manhattan from the Federal Building to specialty attractions like the Tenement Museum.
If this is your first trip to Manhattan, you will likely also want to take the subway up to Times Square for some shopping or people watching. See my recommendations on the best things to do in NYC with kids.
With more time, you can venture into Upper Manhattan and Central Park. Two of my favorite museums are the American Museum of Natural History on the Upper West Side, and the Metropolitan Museum of Art on the Upper East Side.
Make sure you get a view of New York from above at the Freedom Tower, Empire State Building, or Top of the Rock in Rockefeller Center. If you are visiting many of these attractions, be sure to invest in the New York CityPASS to save money on admission fees (and get to skip some lines too!)
Side trip idea: If you have time to spare along the way to the next stop, follow my New York to Boston road trip itinerary.
Where to Stay: On our weekends in NYC, we have enjoyed staying at the Millennium Downtown, right near the World Trade Center and 9/11 Memorial.
Boston (2 days)
It is time to wrap up your trip with a four hour drive up to Boston. Along the way, you may want to plan a stop in Mystic, Connecticut. Still known for its Mystic Pizza, it is also the home of the Mystic Seaport. This maritime living history museum is a lot like Williamsburg, but from a slightly different era.
Once you arrive in Boston, I think making the waterfront area your home base is great for exploring. If you want to explore many of Boston’s top attractions, I’d recommend investing in a Boston CityPASS.
If you are interested in history, I would make the first stop a visit to the Boston Tea Party Ships and Museum. Here you will learn about the lead up to the Boston Tea Party to understand why the rebels threw all that tea into the sea. Then you can step aboard a replica ship and toss a bale over the side yourself! Afterwards, have tea in the tea room upstairs.
This is very close to both the Boston Children’s Museum and the New England Aquarium, which can balance out your visit. If the weather is nice, I also enjoy a harbor cruise (part of the Boston CityPASS) or you can take a ferry over to some of the harbor islands for a few hours.
Two other ways to explore the history of Boston (and the USA), would be on a walking tour of the Freedom Trail. You can do this self-guided, and spend time at different stops along the way, or taking a guided tour from a costumed docent to get the full story and significance behind each location.
The other fun way to explore is with a duck boat tour. These amphibian vehicles start off on land with a guided tour through the city and then splash into the Charles River for the “boat” portion of the tour. If you haven’t done one of these in another city, the novelty is super fun.
See more tips for visiting Boston with teens.
Where to Stay: We love both the Boston Harbor Hotel and the Intercontinental Boston.
That concludes the U.S. History road trip through the Northeast! There is so much to see, even more to learn, and plenty of fun to be had along the way. I hope you feel inspired to take your kids on a history-filled road trip.
Tamara Gruber is the Founder and Publisher of We3Travel. A former marketing executive and travel advisor, Tamara is an award-winning travel writer and recognized expert in family travel. Tamara is a member of SATW and the Adventure Travel Trade Association, and serves on the Board of the Family Travel Association. She is also the publisher of YourTimetoFly.com and the co-host of the Vacation Mavens travel podcast.
