A 4-Day Long Weekend Williamsburg Itinerary

If planning a long weekend visit to Virginia’s “Historic Triangle”: Williamsburg, Jamestown, and Yorktown, this itinerary will make sure you don’t miss anything.

If you plan your itinerary right, you can enjoy a 4-night trip that blends colonials and roller coasters, archaeology and outlet shopping.

There’s bound to be something everyone in your family will enjoy.

Here’s our recommended 4-day Colonial Williamsburg, Jamestown and Yorktown itinerary.

Day 1

Credit Colonial Williamsburg

Arrive in the area the afternoon before, enjoying some down time at your hotel before beginning today bright and early at Colonial Williamsburg.

Stop 1

Spending some time at the World’s Largest Living History Museum is a great way to start your stay.

Book admission tickets online ahead of time to avoid lines at the visitors center.

From there you can take a shuttle to various stops throughout the historic area or just follow a path out of the visitors center leading to the main attractions.

One of the advantages of walking is that the walkway helps get you into a colonial frame of mind: Bronze medallions on the path, inscribed with a relevant fact and positioned every few feet, take you back in time, from the 21st to the 18th century (“In 1868, you know someone who owns other people.”).

Credit Colonial Williamsburg

If you walk, you’ll also pass Great Hopes Plantation – look for the windmill – a chance to experience a bit of rural life in colonial times, which you can contrast with the town life you’ll see in the main Colonial Williamsburg area.

At the plantation, you might find carpenters making roof shingles, a farmer hoeing a field (feel free to help out), roosters and chickens ranging freely, and bulls sleeping in the sun.

Continue on the sidewalk until you reach the main Colonial Williamsburg area.

Start exploring at the Governor’s Palace and its manicured gardens, which include an arbor of trees and a small maze.

Visit the Palace Kitchen, where a cook prepares a table full of dishes with recipes from a colonial cookbook. Unfortunately, no sampling is allowed.

If you have older kids, consider a guided tour of the Palace interior. There’s often a line, however, so if you have younger kids, you might just want to skip the palace tour.

Stop 2

The Cheese Shop at Merchant's Square Williamsburg

Locals might revolt if The Cheese Shop on Merchants Square ever stopped making their terrific sandwiches, crafted with fresh baked bread and top-notch cheeses and meats (try the Virginia ham on French bread).

This local institution is justifiably mobbed during lunch hours. There are two lines: one to order, one to pickup. Tables are available outside but many people carry out and picnic elsewhere.

Stop 3

Afterwards, you can stop next door at Wythe Candy and Gourmet Shop to pick up some fudge, chocolate-covered Virginia peanuts, or caramel apples.

Walk up Duke of Gloucester Street, the main street of Colonial Williamsburg, stopping in at the various stores and trademen workshops along the way – blacksmiths, tinsmiths, candlemakers, carpenters.

The apothecary is particularly fun; onsite historic interpreters answer any questions you might have about 18th-century ailments and cures. In the milliners shop, seamstresses work on pretty bonnets and lace shawls.

Stop 4

Raleigh's Tavern in Colonial Williamsburg
Credit Colonial Williamsburg

In the late afternoon, revolutionary officers might be out in front of Raleigh’s Tavern “recruiting” soldiers to fight in the battle of Yorktown. Fall in line and they’ll teach you some marching moves ahead of the daily fife and drum parade down Duke of Gloucester Street to the field behind the Courthouse.

There you’ll get a front-row view as General George Washington addresses troops, and local militia give cannon salutes.

Stop 4

Chowning's Tavern in Williamsburg
Credit Colonial Williamsburg

You can have dinner at one of the colonial-themed restaurants, such as Kings’ Arms or Chowning’s Tavern. They usually require reservations ahead of time and can be pricey, but it’s a good opportunity to try the types of foods that Alexander Hamilton and his pals might have enjoyed.

Day 2

Stop 1

Yesterday was Williamsburg, tomorrow you can visit Jamestown and Yorktown, but sandwich some pure guilty fun between the historic attractions by heading to Busch Gardens today.

If you have little kids, start at Sesame Street Forest of Fun, with its gentle rides and character meet-and-greets. Your older kids will probably want to hit the roller coasters, which range from the classic Loch Ness Monster to Griffon (which boasts a terrifying 205-foot, 90-degree drop).

If it’s a hot day, there are flume rides that make a splash.

Expect fairground fare: corn dogs, crepes, nachos, turkey legs, funnel cakes.  

This is a whole day activity!

Day 3

Head to Jamestown this morning, site of the first permanent English settlement in the New World. A couple attractions explore the history of the place.

Stop 1

Credit Colonial Williamsburg

Jamestown Settlement is a museum of 17th-century Virginia history and culture, with exhibits inside and a re-created Powhatan Indian village, ships, and fort outside.

Historic Jamestown contains the original site of the fort.

At the visitors center, try to catch one of the talks given by enthusiastic staff. They highlight the settlement’s dramatic main events, such as “the starving time” of winter 1609-10, when some 150 settlers were reduced to 60, and those remaining ate their horses and dogs, and rats and turtles to survive.

Evidence at the active archaeological site suggests that they may have even resorted to cannibalism.

Then stroll outdoors to the surprisingly small site of James Fort, where you’ll see signs of current archaeological digs taking place. Outside the wooden palisade marking the fort’s boundaries, there’s a statue of Pocahontas, the Powhatan princess who was kidnapped by the settlers and held in James Fort, where she met and ended up marrying Englishman John Rolfe.

There are so many interesting stories at Jamestown. There is actually now a TV series on it.

Stop 2

In the afternoon, drive about half an hour east and jump forward in time about 150 years when you visit the American Revolution Museum at Yorktown.

Interactive displays, films, and nearly 500 artifacts convey the causes of the war; the major battles, including Yorktown, where the decisive battle that effectively ended the war took place in 1781; and the impact of the revolution to this day.

Particularly impressive is an immersive widescreen 4D film about the siege of Yorktown – complete with the smell of camp coffee, and the feel of fog, wind, and rain.

The outdoor living history encampment offers opportunities to try your hand at candle-dipping and stripping flax in preparation for weaving into linen.

After a live musket demo, visitors can feel how heavy an actual musket weighs.

You can duck into a camp tent, which looks tiny from the outside but surprisingly slept about six soldiers each.

Before or after exploring the museum and grounds, you can have a bite at the casual onsite café, serving sandwiches, pizza, and mac and cheese.

There’s a lot to experience here, so allot at least four hours for your visit.

Day 4

Credit Simon Group | Williamsburg Premium Outlets

On the way back to the DC area, ease the transition back to the 21st century with a stop at Williamsburg Premium Outlets, with Carter’s, Janie & Jack, Kate Spade, and more.

Where to Stay

Ideally, base yourself at family-friendly lodging that comes with a kitchen, so you can save money by cooking some meals instead of eating out, and with other activities so the family can enjoy some downtime just on the property.

The Historic Powhatan Resort, for example, offers 3-bedroom suites with full kitchens.

It also has indoor and outdoor pools, tennis courts, onsite general store, mini golf course, playground, and more.

The down side to this resort: dealing with timeshare sales. If you are not interested, simply decline politely the offer to meet with a sales person.

Source: Great Wolf Lodge

Although it doesn’t offer rooms with kitchens, Great Wolf Lodge Williamsburg is another fun lodging option.

It boasts 79,000-square-feet of water park action, most of it indoors. 

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OK Editorial Team

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