Virginia Road Trip

If you want to take your children on a trip through American history, one of the best places to visit is Virginia. From America’s earliest days to its most recent historical events, a week-long road trip through the heart of Virginia is a must-do for all Americans. While not a native Virginian, I’ve lived here since 2000 and feel as if it’s home. There’s so much to see that you might want to make it a 2-week stay!

Be sure to download the Virginia History Trails app before your visit!

**Note: Virginia is currently lifting many of its COVID restrictions. Be sure to check the latest regulations before your visit.**


Image taken from Google Maps

Day 1: Journey along the James

Fly into Richmond International Airport, rent a car, and drive east to Williamsburg (1 hour drive). Ignore GPS and take the scenic way, Virginia’s historic Route 5, along the James River. Be sure to download the GPS-enabled Historical Highway Markers tour for the trip!

Stay: Kingsmill Resort, Williamsburg: Reserve at least three nights at this expansive, family-friendly resort along the James River. Your kids will love the lazy river at the pool, and you’ll love the option of staying in a condo with a kitchen – a necessity on a long trip with kids! 

Eat: On your drive, stop for lunch at one of my favorite restaurants, Upper Shirley Vineyards, for an amazing picnic right on the James River. It’s a perfect stop to get the wiggles out after a long plane or car ride! For a casual dinner, eat at the award-winning Pierce’s Pitt BBQ before hotel check-in.

Do: Driving along Route 5, stop at one of the historic plantations. My favorites are Berkeley Plantation or Shirley Plantation. Civil War enthusiasts should visit the Malvern Hill Battlefield (part of the Richmond National Battlefield Park) along the way.


Day 2: Ye Olde Colonial Times

Drive into Colonial Williamsburg and park at the Visitor Center. You can walk or take a shuttle to all of the historic attractions along Duke of Gloucester Street. Be sure to read my review to plan your day! If you have small children, plan for a half-day of historic fun before coming back to the hotel for naps and pool time. There is a lot of walking in the colonial area so be sure to bring strollers as needed! Also note that this day will be spent mostly outside so plan accordingly!

Eat: Have an authentic 18th century lunch at Chowning’s (pronounced “Chewnings”) Tavern. Don’t forget to visit the Raleigh Tavern Bakery for ginger cookies! For dinner, on your drive back to the hotel, stop at Old City Barbeque where you have to get the smoked pimento cheese appetizer!

Do: For non-historic fun, visit Kidsburg or Go Ape! Treetop Adventure


Day 3: Where the “World Turned Upside Down”

Get your Hamilton: The Musical soundtrack playing as you spend the day in Yorktown. From one of the best museums in the country to the actual site where Hamilton told his soldiers to “take the bullets out your guns,” this little town is a treasure trove of history. Be sure to read my review to plan your day. 

**Pro tip – Buy the combo pass as you’ll be visiting the sister museum in Jamestown tomorrow**

Eat: The lovely riverwalk has several restaurants right on the York River, perfect for lunch with a view! For dinner, go back to the hotel or eat at Busch Gardens.

Do: If you only spend a half-day at Yorktown, spend the early afternoon or evening at Busch Gardens, where you can “visit” other countries. It’s my kids’ favorite theme park!


Day 4: Capital to Capital

Check out of the hotel and drive to Jamestown – Virginia’s first capital (20 minutes). Visit the awesome Jamestown Settlement Museum and Historic Jamestowne (read my review to plan your day). Be there right when it opens and plan to stay through lunch. Drive through Richmond – Virginia’s capital (1 hour from Jamestown) on your way to your destination of Charlottesville (1 hour from Richmond). 

Stay: Boar’s Head Resort, Charlottesville: Spend at least two nights at this luxurious, child-friendly resort in the college town of Charlottesville.

Eat: A unique lunch experience is Charly’s Airport Restaurant at the tiny Williamsburg airport. You can watch private planes taxi on the runway while eating! Our plane obsessed kids love it here!

Grab a snack in Richmond at Sally Bell’s – its upside down cupcakes are my favorite!

For dinner, eat at the hotel or do our family’s favorite after a long day of travel – room service!

Do: After Jamestown, drive through Richmond. For a driving audio tour, download this app.

Choose one or two of my recommended stops: Richmond National Battlefield Park and American Civil War Museum for Civil War enthusiasts, Virginia Museum of History and Culture (closed through July 1st), Black History Museum and Jackson Ward walking tour, Historic St. John’s Church (especially if a reenactment is on the schedule!), and the grounds of the Virginia Capitol.

For non-historic fun, your kids will love the hands-on Science Museum of Virginia


Day 5: Mother of Presidents

The Charlottesville area was the home of three of our nation’s first five Presidents, and Virginia is known as the Mother of Presidents (8 and counting!). Start out the day by visiting Thomas Jefferson’s home, Monticello (be sure to get tickets well in advance!). After lunch, visit James Monroe’s nearby home, Highland, only 10 minutes away, and then tour Mr. Jefferson’s masterpiece – the University of Virginia. If you’d rather see James Madison’s home, Montpelier, it’s just a 45 minute drive away (highly recommended in the fall – it’s gorgeous there!).

Eat: After touring Monticello, stop at the next door Michie’s (pronounced “Mickie’s”) Tavern for hearty southern fare. Drive up the mountain to Carter Mountain Orchard for a snack break – its apple cider donuts are amazing! For dinner, eat at the downtown mall (pedestrian zone) in Charlottesville. If you did the side trip to Montpelier, eat at the famous Gordonsville BBQ Exchange.

Do: Touring the Presidential homes will take the whole day. If you have young children, don’t miss Monticello but skip Highland and Montpelier. Take them to the nearby Carter Mountain Orchard or Chiles Peach Orchard to pick their own fruit instead! Be sure to check what’s in season before going. 


Day 6: Civil War to Civil Rights

Leave Charlottesville and drive to Appomattox Courthouse (1.5 hour drive). Visit Appomattox Court House National Historical Park and the American Civil War Museum – Appomattox branch. Drive to Farmville (35 minute drive) for lunch and evening activities.

Stay: Hotel Weyanoke, Farmville: This newly opened boutique hotel in quaint downtown Farmville has an amazing rooftop terrace! 

Eat: Farmville has a cute downtown with several good restaurants. We love the kid-friendly Macado’s or check out these other options.

Do: After lunch, rent bicycles and head out on the High Bridge Trail. Read my review here for more details! Then tour the Moton Museum to learn about Farmville’s important place in Civil Rights history. There’s also a Civil Rights walking tour throughout downtown Farmville. 

If you have a World War II history buff in your family, take a short detour to Bedford (1 hour west of Appomattox) to visit the National D-Day Memorial before driving to Farmville.


Day 7: Saying Goodbye

Drive from Farmville to Richmond International Airport (1.5 hour drive). Depending on time, you can retrace the route of Lee’s Retreat during the last week of the Civil War or add in a visit to Petersburg National Battlefield Park.

If you have more than a week, consider adding in a trip to the Washington, DC area or Virginia Beach! Both are 3 hour drives from Farmville and have many fun, historical things to do!


This itinerary barely scrapes the surface of all of the historical sites in Central Virginia but gives you a good overview of its importance in American history. From the earliest English settlers in 1607 to important Civil Rights events, Virginia truly is for history lovers!


Helpful hints:

  • Weather: Virginia has four full seasons. Summer can be very HOT, especially in Williamsburg and Richmond. Drink lots of water, and plan for pool time at the hotel!
  • Traffic: Traffic shouldn’t be a huge problem in Richmond, Charlottesville, or Farmville. I-64 to Williamsburg is usually very crowded, particularly in the summer. Stick to my itinerary and take the scenic Route 5 to avoid most traffic.
  • Crowds: Colonial Williamsburg and Monticello are the main places where you will run into crowds. Reserve tickets in advance and plan accordingly.
  • Transportation: Richmond International Airport is one of the easiest airports to navigate. To do this tour, you will need a car.
  • To prepare for your trip, be sure to check out our local NBC station’s podcast, How We Got Here. It’s fabulous and would be a perfect listen on this road trip!

Books to Read:

I’ve compiled a list of my favorite books about Virginia at my Bookshop.org shop (affiliate links).

A few not found on Bookshop.org are (these are Amazon affiliate links):

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