Achieve the Impossible! Make U.S. History Fun on a Northeast Road Trip

Somewhere around middle school, most students in the United States will study U.S. history. This is perfect timing for a Northeast road trip to hit many of the main historic sites that are so relevant to the founding of our country.

We have certainly found 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 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 linked to our colonial history and fight for freedom on this northeast road trip.

Later you can tackle other themes like a Civil Rights road trip, Trail of Tears, Lewis & Clark, etc. 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.

To save time, I would recommend flying into Norfolk International Airport. 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.

Northeast Road Trip Itinerary

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Williamsburg (2 days)

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.

I would recommend staying at the Woodlands Hotel & Suites in Colonial Williamsburg. Depending on where you are coming from, you may want to settle in and enjoy the pool, or you can head right over to Colonial Williamsburg.

Colonial Williamsburg in a day (or less) -- reenactments on the village green

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. Older kids may enjoy exploring through the  RevQuest spy game. 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 (or two) to enjoy Busch Gardens amusement park or the Watercountry USA water park.

Jamestown & Yorktown (1-2 days)

Jamestown Settlement -- What to do on a road trip through Virginia with Kids

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 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, also known at the Yorktown Victory Center, 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 (at least 3 days)

It is a two and one-half hour drive from Williamsburg up to Washington D.C.. 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 recently enjoyed our stay at The Darcy (a Curio by Hilton Property) and got a great deal!

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. Intersperse museums with bike tours through the Tidal Basin, walks through the monuments, and time playing on the National Mall. You can always come back to see the rest. 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.

Find out more ideas for visiting Washington DC with teens.

Baltimore (1-2 days)

Baltimore Inner Harbor

From Washington D.C., it is just an hour drive up to Baltimore. While there are a few 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.

Twice we have stayed at the Hilton Baltimore and I love the location. It is 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.)

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.

Whatever you do, don’t miss breakfast at Miss Shirley’s.

Philadelphia (2 days)

Every northeast 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? Try to stay in the historic city center to make everything very accessible. The Kimpton Hotel Monaco Philadelphia is the perfect location.

Start off at Independence Hall. Tour tickets are first-come, first-serve unless you book in advance so make sure you otherwise get there early. 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.

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.

New York (at least 2 days)

Statue of Liberty

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. On our weekends in NYC, we have enjoyed staying at the Millennium Hilton New York Downtown, right near the World Trade Center and 9/11 Memorial.

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 (and maybe catch a show in the Theater District or stop by the Hamilton merchandise store.)

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!)

Boston (2 days)

Boston Harbor Cruise

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. And, if you really want to go back to Pilgrim days, you need to plan a stop or day trip at Plimoth Plantation, in Plymouth, Massachusetts. The John Carver Inn makes a great stopping point here with its family-size suites and indoor pool/waterpark.

Once you arrive in Boston, I think making the waterfront area your home base is great for exploring. We love both the Boston Harbor Hotel and the Intercontinental Boston. I’ve also put together some tips for visiting Boston on a budget. Tip number one is to invest in a Boston CityPASS if you will have at least two full days and want to visit many top attractions.

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 colonist 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.

Get Road Trip Ready

So there you have it. You can pull off a Northeast road trip in two weeks, although if you have longer there is still so much more to see. I also have ideas for planning a New England road trip if that is more your speed.

Road Trip Resources

How to Prepare

Before any family trip, I like to prepare kids for what they are going to see and learn, especially if there is a big educational element to the trip. If you are doing this trip in middle school or later, they likely have a good background from what they have learned in school. Or, if they have listened to the Hamilton soundtrack a million times like my kid, they at least know something about early U.S. history.

Have you taken a road trip through the Northeast? I’d love to hear your thoughts and tips in the comments below.


Northeast road trip itinerary for visiting Williamsburg, Jamestown, Washington DC, Baltimore, Philadelphia, New York and Boston #roadtrip #northeast #boston #familytravel


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Publish Date: April 9, 2018

2 thoughts on “Achieve the Impossible! Make U.S. History Fun on a Northeast Road Trip”

  1. I’m planning an educational/homeschool fieldtrip this summer and this is just what I was looking for! Thank you for all the information.

    1. Good luck! Now is certainly the time to homeschool and fieldtrips/road schooling brings it all to life.

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