American Colonial and Revolutionary History Road Trip

Touring Boston, Philadelphia, and Virginia with kids!

Looking for a ready-made American history road trip itinerary? We’ve got it! This itinerary starts in Boston, MA and ends in Williamsburg, Virginia, and hit highlights of American colonial and Revolutionary history. Civil War history can be added, as well!

paul-revere-freedom trail

Days 1-3:

Start your trip in historic Boston. Walk the Freedom Trail, visit Faneuil Hall, and see Old Ironsides. Older kids will love seeing Paul Revere’s house and the historic cemetery.

Where to stay: be part of history when sleeping in the Custom House building, which is now operated by Marriott Vacation Club.

Days 4-6:

Drive down the Eastern Seaboard to Philadelphia to continue your Revolutionary history. In Philly, see where America began in Independence Hall where the Declaration of Independence was signed. Tour the Constitution Center, see the Liberty Bell, and visit the site of Ben Franklin’s home and offices.

Where to stay: Hotel Monaco Philly is located directly across the street from Independence Hall. Need we say more? 


Day 7:

Head out of Philly and stop at Valley Forge, PA. Spend half a day on the self-guided auto tour of Washington’s winter camp, including his officer’s quarters and many bunkhouses of enlisted men. In the afternoon, drive either to Gettysburg, PA to learn about the Civil War battle (plan to stay two days), or take the long road trip down to Williamsburg, VA.


Day 8-10:

Spend three days touring Colonial Revolutionary City in Williamsburg, VA. Take the time to visit the various shops and tradesmen, eat in the pubs, and book an evening tour or two. Definitely walk from the Visitor’s Center to Great Hopes Plantation, and play RevQuest if you have older kids or teens.

Where to stay: Williamsburg Woodlands is within walking and shuttle distance of Revolutionary City, plus includes a splash play area, mini golf, and a pool. 

Day 11:

Devote one full day to touring Jamestown, VA. Located adjacent to Williamsburg, this original site of the Jamestown Settlement has two parts: the original national historic site, where kids can see ongoing excavation in progress, and the recreated historic settlement and fort. Take time to tour the museum as well!



If there’s time, round out your historic road trip with a visit to Washington DC to see the actual Declaration of Independence and the flag that inspired the Star Spangled Banner.

About the author

Amy Whitley AUTHOR: Amy Whitley is the founding editor of Pit Stops for Kids and content editor of Trekaroo. She writes on staff monthly as a family travel expert at Go Green Travel Green and Practical Travel Gear, and contributes to Outdoors NW as an outdoor adventure traveler. Find Amy at Google.




  1. Great list! I really believe visiting the places they learned about from history books helps the kids remember the events better. I know it helps me. If you were able to spend a bit more time in Massachusetts, I’d suggest also visiting the Minuteman National Park in Lexington / Concord, the Plimoth Plantation, and Salem.

  2. Yeah, still here and still ogling these. Writing down a large list so we don’t miss anything this time ’round. Gettysburg was amazing especially from an outside perspective but all of these are completely amazing to me.

Leave a Comment