I’m a historian & I planned the ultimate trip to Virginia’s historic triangle

Looking for a Virginia getaway that brings history to life? Check out a historian’s guide to visiting Virginia’s historic triangle.

As a historian, any getaway that comes with a side of history sounds good to me, but I’ve loved Virginia’s “historic triangle” since I was a child. This area, on a peninsula bound by the James and York Rivers, includes three of America’s most famous historic sites: Jamestown, Yorktown, and Colonial Williamsburg, which make up the three points of the triangle.

One of the best parts of the historic triangle is that all three of its points have fun and fascinating visitor attractions for guests to explore—and growing up outside of Washington, DC, visiting them for family trips was part of what sparked my interest in history. Better yet, academics and archaeologists are always uncovering new facts about Virginia’s history in the area, meaning that there are always new things to learn and explore at all three sites.

While a trip to the area can take as much or as little time as you like, long weekends are always a popular choice, especially when the weather is nice, as many of the best things to do are outdoors. With that in mind, I’ve planned a three-day trip through 400 years of Virginia history. This itinerary can be modified to suit you or your family’s needs, but have a look and get ready for a trip to the past!

Day 1: Jamestown and Yorktown

Your first day in the historic triangle is going to be a trip in a time machine, and we’re setting the dial all the way back to the seventeenth century. Jamestown, originally spelled as “Jamestowne,” was the site of the first permanent settlement established by the English in North America in the early seventeenth century. Jamestown was built on land belonging to the Powhatan people and was the site of the famous meeting between John Smith and Pocahontas.

Today, the site of Jamestown is a museum and archaeological dig, uncovering more and more history all the time. Visitors can explore the site of the original fort, learn about life in the early years of Jamestown, and tour the remains of what was once Virginia’s liveliest port town on the James River.

Next up, it’s time for a visit to Yorktown. Possibly the least-known corner of Virginia’s historic triangle, Yorktown was the site of General Cornwallis’ surrender, ending the Revolutionary War and cementing the future of the United States as an independent nation. Today, the battlefield at Yorktown is part of Colonial National Historical Park, maintained by the National Park Service. You can visit the battlefield and historic Main Street, or take an audio tour of the park from the comfort of your vehicle to learn about Yorktown’s history from the eighteenth century to today.

Day 2: Colonial Williamsburg Visitor’s Center and Tours

Colonial Williamsburg is one of the largest and most famous living history attractions in the country, and you’ll need to get the lay of the land before you dive in. The best place to do that is at the Visitor’s Center, which is why it makes an ideal first stop on your second day of historical touring. At the Visitor’s Center, you can plan out your time in the living history section of Colonial Williamsburg and pick up passes that will let you into attractions and tours. While you’re there, make sure to take in a screening of “The Story of a Patriot,” the longest-running film shown anywhere in the United States!

After the Visitor’s Center, it’s time to head over to Colonial Williamsburg itself. Once there, be on the lookout for any building with a (British) flag outside the door, as this means that inside is a tour, reenactment, or demonstration. You can pop your head in to meet a colonial milliner, apothecary, innkeeper, and more, as well as touring the grand Governor’s mansion, and getting lost in the maze outside. Even though you’re not being punished, like someone in the eighteenth century would have been, be sure to get a photo of yourself in the stocks outside the courthouse; it’s a Williamsburg tradition!

While many of the top living history attractions and shops for snacks and souvenirs are located along Duke of Gloucester Street, the main road through town, you should also make a point of checking out the side streets. This goes double if you or your family like animals, as you might run into some friendly sheep or other farmyard friends! Remember, though, that touring Colonial Williamsburg requires a lot of walking, so be sure to wear comfortable shoes, stay hydrated, and be ready to take time to rest, swim, or enjoy a leisurely dinner later in the day.

Day 3: Merchant’s Square and a Tavern Treat

After all of your adventures through history, it’s time to gently ease your way back into the present day. But you’re not quite done with your trip through Virginia’s past!

Start the day with a wander through Merchant’s Square, the collection of modern shops and restaurants with colonial exteriors that make up “downtown” Williamsburg. Be sure to swing by the famous Peanut Shop, where you can pick up a snack for the road, or some made-in-Virginia treats to bring back as souvenirs—assuming you don’t eat them all yourself! Other highlights include the candy store, the cheese shop, and, if you have the time, a wander through the historic campus of the College of William and Mary.

Finally, it’s time for one last wander down Duke of Gloucester Street for a hearty farewell lunch. No trip to Virginia’s historic triangle would be complete without a trip to one of Colonial Williamsburg’s carefully restored taverns. Stop by the King’s Arms Tavern for a full feast of soups, salads, and roast meats, all based on authentic eighteenth-century recipes. And be sure to raise a glass of locally-made ginger ale in a toast to the Revolution!