2 Days in Virginia’s Historic Triangle with Kids: Williamsburg, Jamestown & Yorktown Itinerary

Growing up as a Virginian in the 1980s, Colonial Williamsburg was always on everyone’s radar for family road trips. We’d go for a weekend getaway to immerse in our Commonwealth’s early history, and later to bring my brother to and from the adjacent College of William & Mary. In short, I spent the first two decades of my life as a “regular”. But years of west coast living and the allure of international travel keept my family away… until now!

This year it was finally time to bring my own kids to Colonial Williamsburg so they could discover what makes it such a unique place. I think the best age for Colonial Williamsburg is late elementary school and middle school – kids have learned about the colonial history of America and the Revolutionary War, but they’re still young enough to appreciate costumed interpreters portraying historical people. In short, we’re about to exit the “sweet spot” with our older kid.

Now that I’ve finally visited Colonial Williamsburg as an adult, I have plenty of tips to share with you – including why you should include the surrounding Historic Triangle sites in your itinerary, where to stay in Colonial Williamsburg and other add-on experiences in the area in case you’re looking to build a longer itinerary for Virginia with kids. Feel free to use the table of contents below to jump around to the sections that will help you the most!

What is Colonial Williamsburg, and a brief history of “Historic Triangle”

This blog post isn’t going to turn into a history lesson, but it’s helpful to brush up on some basics before you start planning so that you can decide what to prioritize for your family.

Virginia’s Historic Triangle includes three towns, which I’m listing here chronologically in order of when they were important in history:

• Jamestown – The first permanent English settlement in North America, founded in 1607. It was poorly run from the beginning and eventually destroyed by a series of fires, the last one in 1698.
• Williamsburg – Initially founded as Middle Plantation in 1632, Williamsburg became the capital of Virginia in 1699. In the 18th century you would have seen notable figures like Thomas Jefferson, Patrick Henry, George Washington, James Madison walking the streets and dining at the local pubs. It has also been home to the College of William & Mary since 1693.
• Yorktown – Yorktown was built in 1691 as a tobacco port on the York River (which flows into the Chesapeake Bay), as tobacco cultivation was virtually the only profitable industry in the Virginia colony. It’s best known as the location of America’s victory in 1781, when George Washington’s forces and their French allies defeated the British army.

The three towns are all within a 20 mile range on the Virginia Peninsula, sandwiched between the James and York Rivers. Due to the harsh conditions in its early years and subsequent fires, there’s no town to walk through at Jamestown today – though that doesn’t mean it isn’t worth visiting, as I’ll explain shortly. Yorktown was always a small town and remains so today.

While Williamsburg became the colonial capital in 1699 and flourished through the 18th century, the capital was moved to less-vulnerable Richmond late in the American Revolution. The College remained in Williamsburg (though it closed during the Civil War and again in the 1880s), but over the first 150 years of independence the town stagnated.

Finally, in 1923 the local Episcopalian convinced the wealthy Rockefeller family to finance a restoration of the town’s historic core to create a place that paid homage to colonial life and history – one of the first prominent “living history museums”. The first buildings of Colonial Williamsburg opened in 1932 and in the years that followed, many of the current features took root like period-accurate dress and artisans becoming world-experts on the “old ways” of crafts like weaving, printing and smithing.

Why is all of this background relevant? Because if you really want your visit to Virginia with kids to serve as a history lesson, you could spend three days in the area and strategically visit them in sequence! If you don’t have quite that much time you’ll have to pick and choose what to do.

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Williamsburg logistics

Back when I was child in the stone ages, Colonial Williamsburg was almost exclusively a driving destination. But today it’s accessible from all over the US (and the world) thanks to easy and affordable flights.

While the closest airport is Newport News, schedules are far more robust at both Richmond and Norfolk – each is roughly an hour from Historic Triangle, though the traffic to Norfolk can be intense at times. We flew on Southwest thanks to our companion passes – our kids each fly for just $5.60 each way! On our original itinerary we flew into Richmond, rented a car to get around for the weekend and then we were slated to fly out of Norfolk since it’s closer to Yorktown.

Your other option is to fly into the DC area and drive or take the train down. We accidentally ended up driving from Yorktown back to Baltimore for our return flight rather than flying there from Norfolk, and the drive was pleasant and easy on a Sunday afternoon (we took the state routes that are east of I-95).

Taking the train is fine if you primarily want to visit Colonial Williamsburg, as the train station is just a 10 minute walk from the entrance. Everything within CW is walkable and there’s also complimentary bus service that you can ride just by flashing your admission ticket. You could also grab an affordable Uber to nearby Jamestown, but Yorktown is quite a bit further and lacks good public transportation. Alternatively, if you’re taking the train you could book this excellent tour that covers Jamestown and Yorktown – more on that option later.

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Where to stay in Williamsburg, VA

While I’m generally a fan of using credit card points to get free stays, in Williamsburg I was happy to stay at an “official” partner hotel – but I’ll share my secret to getting it almost free.

We stayed at the Williamsburg Woodlands Hotel & Suites. This is a pretty big property with almost 300 rooms, and it plays host to events like sports tournaments. There are some nice amenities for families like a pool with a splash area, playground and 24 hour putt putt!

But the best amenity at all is that the Colonial Williamsburg Visitors Center is in the hotel parking lot. You can see it right from the front door! If your family is like mine and always going slower than expected in the morning, this is a huge benefit. You don’t have to worry about where to park or how to get between the historic area and the hotel, because it’s all right there. To get to the historic area, you can either walk 15 minutes on a very pretty, paved path through the woods or you can take the free shuttle bus from the visitors center to the Governor’s Palace.

Rooms at Woodlands are reasonably priced, and it was only a $10 difference to reserve a suite rather than a regular room. There was also no charge for a roll-away bed, so my kids didn’t even have to fight about sharing a bed.

The only downside of Williamsburg Woodlands is that the buffet-style continental breakfast was a madhouse and not all that satisfying. Perhaps we’ve just gotten spoiled by hot breakfast! Options included cereals, bagels, yogurt, waffles, oatmeal, hard boiled eggs etc. On our check-out day (when we were heading to Jamestown by car) we opted for a much better breakfast at nearby Colonial Pancake House – plenty of gluten-free and regular options here!

So how did I score this ultra-convenient hotel for free? First up, I booked it through the Capital One Travel portal using our Venture X credit card. That card comes with a $300 annual travel credit, which covered most of the $453 hotel cost for two nights; the balance also earned us 10 points per dollar that we can use for future travels, worth about $23. Next, I went to the official hotel website and saw that they were running a great special: book one night, get the second night at half-price. The nightly rates weren’t identical but the official site was $87 cheaper. I picked up the phone and called Capital One Travel, and they were happy to issue me a credit for the difference – it doesn’t expire and can be used toward our future travels as well! My outlay after all those savings was in the neighborhood of $50 for two nights. I really love the Capital One Venture X for situations where a chain hotel on points isn’t well-located or is a bad value.

Our neighbors recently stayed in one of the 2 bedroom houses offered by Colonial Williamsburg and they were really pleased with the amount of space! The locations are great, and they’re all in carefully restored buildings that have been updated with modern comforts like air conditioning.

If you prefer a more refined experience without an exorbitant price tag, my brother usually prefers to stay at the Williamsburg Lodge now that he’s past his student days. It’s part of Marriott’s Autograph Collection so you’ll collect nights toward status. Unfortunately it’s not a great points redemption option.

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Historic Triangle + Colonial Williamsburg 2 Day Itinerary

Day 1: Colonial Williamsburg

Start with quick breakfast at your hotel for convenience and then head to the Colonial Williamsburg Visitors Center, in the parking lot of Williamsburg Woodlands Hotel & Suites. We purchased our tickets in advance so I stopped at the desk to pick up our physical passes and a map (which I didn’t really need).

You’ll want to catch the 10am showing of Williamsburg: The Story of a Patriot. The movie was filmed right here in Colonial Williamsburg in 1957 (wow!) to orient visitors to the buildings, people and stories they’ll encounter as they visit the town. It’s a little cheesy by today’s standards, but even my teen found it interesting. Fun fact: By some accounts this is the longest-running movie of all time.

It’s up to you whether you prefer to walk or take the free bus into Colonial Williamsburg. We took the bus in the morning since it was pulling up when we needed it, but we walked back at night and found it pleasant and easy. If you have a stroller, you’ll need to fold it for the bus.

No matter how you go you’ll wind up on the back side of the Governor’s Palace, just steps from Duke of Gloucester Street (affectionately referred to as “DoG Street”, like the pet). This is really where the fun begins! DoG Street and the surrounding blocks are full of amazing experiences you won’t find anywhere else including performances, tradespeople and stores.

Read more: 6 Colonial Williamsburg “Do’s and Don’ts” For A Perfect Visit

It’s really important to understand that the schedule changes daily for many activities – some are only offered once or twice per week. Thankfully it’s posted a few months in advance, so on a multi-day trip to Historic Triangle you can be strategic about which day you choose to spend in Colonial Williamsburg. Dedicate a few minutes while you’re planning to studying the schedule on the official website and jot down your priorities in a note on your phone – unfortunately the “trip planner” section of the website is virtually useless. Try to leave some flexible time in your day to wander in and out of different buildings, which is half of the fun.

Here’s what our tentative schedule looked like to give you an example, though we didn’t make it to a few of the scheduled activities in the end since we were enjoying our time chatting with craftspeople:

Feel free to stop anyone you see in historic dress to ask them questions about themselves, their personal story or their view on issues of the day – slavery, taxation, religion and more. Interpreters spend up to several months researching and learning about the individual they portray and will gladly engage with you. But they’re also not prohibited from “breaking the fourth wall” if a modern analogy will help you better understand the Colonial era they inhabited.

Don’t miss the Weaving Shop! The interpreter here shared one of the most fascinating explanations we’ve heard about the Colonial economy and its connection to the war effort, and that’s coming from someone who spent many years learning about Virginia history. It was our family’s favorite stop! (And apparently we aren’t alone in loving that stop – that’s a fascinating article about how CW is meeting the current moment.)

We also had a great experience at the dress maker’s shop and learned a lot at the print shop. There are farms where you can meet some of the typical animals of the time, an Army encampment where there are typically several interactive demonstrations per day and an American Indian encampment showcasing Indigenous life in the region. Some popular stops like the apothecary weren’t open the day we visited unfortunately. You’ll know what’s open when you’re in Colonial Williamsburg by the “Continental Union” flag flying out front! I’d also suggest hopping on this free tour if it’s offered when you are visiting.

You can take a guided tour of the Governor’s Palace (which is a reconstruction) for most of the day or opt to explore on your own beginning at 4pm. The actual tour schedule isn’t listed. on the website, so you might want to do this first thing in the morning if you’re interested or on your way back from lunch. We arrived just after the last tour had departed so we visited on our own but there were costumed interpreters in each room to share information.

I do want to point out one performance that you need to put on your schedule and another you should probably include. First up is the Fife & Drum March, the several-times-weekly procession of musicians along DoG Street. I still remember it vividly from my own childhood and I’m glad I could share it with my kids! The military-style procession’s starting time and location vary a little by day but you’ll see about 40 young people in full costume parading through Colonial Williamsburg playing the tunes of the era. It lasts about 15-20 minutes and you’ll want to catch the whole thing – many people (including me) walk next to the procession. Fifes & Drums members start in 5th grade and continue through high school, so you’ll find the performance in later afternoon on weekdays and mid-day on weekends.

I also really like the interactive Order in the Court activity, which is scheduled for several sessions every day. It’s appropriate for elementary school on up and takes participants through several court cases that actually occurred during the colonial era in Williamsburg! There are numerous participatory roles available, and after each case the interpreter shares the real history (including the outcome).

There are so many other performances, from comedy to music to political debate. There’s no way to see them all in one day! One notable performance does require a separate ticket: the evening program To Hang a Pirate. This is a classic that I remember attending as a kid. It’s a recreation of an actual pirate trial that occurred in the very courtroom where you’ll sit and vote on the fate of one of Blackbeard’s men! It’s such a neat experience that your kids will love, though it’s best for tweens and up since it can be pretty intense. This show is typically available once or twice per week (either once or twice each evening) and is worth arranging your visit around in my opinion. Pro tip: This trial is held in the courtroom inside the Capitol building, which is not the small courthouse in the middle of DoG Street.

I do recommend that you leave CW briefly to grab lunch at The Cheese Shop, just past the western edge of the historic area. It offers simple, excellent sandwiches and plenty of outdoor seating to rest your tired legs after a morning of walking. Pro tip: Head downstairs for a glass of wine while you wait for your order, and ask for a sample from nearby Barboursville Winery.

Unfortunately there aren’t great casual eateries within Colonial Williamsburg – there are taverns (I’ll get to those in a minute), snack shops at hotel restaurants. There are a few good pick-me-up options like Dubois Grocery for ice cream and Raleigh Tavern Bakery for cookies or traditional Ginger Cake. The only quick lunch places these days are Chowning’s Garden Bar, which isn’t open every day and will run you at least $20 per person out the door, and Shields Tavern which serves a fixed menu.

Please don’t think me a hater, though. You should absolutely visit one of Colonial Williamsburg’s taverns for dinner if it’s within your budget! They’re somewhere between historically-accurate fine dining and dinner theater and you’ll learn so much about the culture of the time by going.

There are currently two historic taverns operating for dinner: King’s Arms and Christiana Campbell’s. At the most basic level, Christiana Campbell’s specializes in local seafood like shrimp and crab cakes while King’s Arms offers a more diverse array of options. Both buildings are faithful reconstructions of their historic predecessors. We opted for King’s Arms because it met our family’s dietary needs well and we were not disappointed the food was genuinely good and the overall experience was excellent. Our servers at King’s Arms tavern were costumed interpreters and a musician also joined us for part of the time.

You definitely need a reservation and can expect to be at the tavern for about two hours. Since all of the historic buildings close down at 5pm, you could easily do a 5:15 dinner reservation followed by To Hang A Pirate at 7:30. It’s the perfect end to your very busy one day in Colonial Williamsburg!

Day 2: Jamestown + Yorktown

If you only have two days in Williamsburg and the rest of the Historic Triangle, you’ll need to either have a jam-packed day in Jamestown and Yorktown or be choosy about what you do. I recommend that you visit Jamestown first and Yorktown second for two reasons: first, Jamestown is just 15 minutes from Williamsburg; and second, one of the two sites at Yorktown is accessible much later than everything else you’ll do today.

But first, breakfast. There are actually a lot of great breakfast spots in Williamsburg, but Colonial Pancake House was the clear winner for us. It’s just beyond the eastern edge of Colonial Williamsburg, it has great food and there are plenty of options to satisfy all dietary needs – from pork-free breakfast meat options to actually delicious gluten-free pancakes, waffles and more. There can be a short wait if you arrive at peak time, so try to arrive a little before 9am if you can (or before 8am if you’re going to try to do everything).

Morning in Jamestown

The story of Jamestown, the first permanent English settlement in North America, is told at two different unrelated sites: Historic Jamestowne and Jamestown Settlement. If you grew up visiting Williamsburg and are thinking “why have I never heard of these places?” that’s because they didn’t exist as tourist attractions until the 1990s.

Historic Jamestowne sits on the site of what was the original James Fort and the town that grew up next to it. Part of the property is managed by the National Park Service while the other part is managed by Preservation Virginia, each requiring separate admission. This is an active archeological excavation site and research center. There are almost no original buildings standing here, but there are guided tours included in your various tickets with the goal of bringing this important historic site to life. A few of the tours (typically one or two per day) are guided by costumed interpreters, while others are run by NPS rangers or archeologists.

Pro tip: Your admission to the NPS portion of Historic Jamestowne is covered by the America the Beautiful National Parks Pass. If you have a 4th grader, they can bring the family with their free Every Kid In A Park Pass – but be sure to have them play the game and print out a paper copy of the voucher to exchange with a ranger and receive the actual pass.

Just up the road is Jamestown Settlement, which offers a huge multi-media museum following Jamestown’s history from before its founding in 1607 to its destruction in 1699. The museum does a great job of honoring the three distinct cultures and peoples that contributed to Jamestown: the Powhatan who originally inhabited the region, the Angolans who were brought by force and the English who sought fortunes in the Colony. There’s an excellent mix of artifacts, movies and written panels to make the information accessible to a variety of readers. When I asked my husband if there was anything he would have changed about our day, he highlighted wanting more time in the museum (and I agree).

Outside at Jamestown Settlement there’s a living history that used to be called Jamestown Festival Park. It includes a recreation of James Fort, a Powhatan Village and three boats that brought colonists to Jamestown. You can touch and experience everything with the guidance of costumed interpreters; there are hands-on activities, gun demonstrations and more. It’s like Colonial Williamsburg in many ways, but much smaller.

When trying to piece together all of the parts of our Historic Triangle itinerary, I knew it would be difficult to squeeze in everything. We opted to skip Historic Jamestowne in favor of Jamestown Settlement. I feel satisfied with that choice, though I’d love to go back sometime to check out the archeological excavation. For kids, Jamestown Settlement makes the history approachable and engaging; for adults, the museum offers a wealth of information that illuminates a facet of history that’s often glossed over with a sentence in history books. I also really appreciate that the museum confronts Virginia’s history of slavery head-on.

In total we spent about three hours at Jamestown Settlement, including the museum, the living history exhibits and a quick lunch in the on-site cafe. The food there was pretty good, with enough variety to satisfy our family. In such a packed day, it was extremely convenient to stop there!

Afternoon in Yorktown

Our next stop was the American Revolution Museum at Yorktown (ARMY), which is also run by the Jamestown-Yorktown Foundation and organized similarly: there’s a well-done, contemporary, multi-media museum and a living history exhibit outside. This site and Jamestown Settlement were covered by a discounted combo ticket we purchased.

As any Hamilton lover knows, the Battle of Yorktown in 1781 (mostly) marked the end of hostilities between British and American troops in the American Revolution. The museum here covers the entire war, again with immersive exhibits and meaningful artifacts. We didn’t spend as much time in the museum itself because our whole family has a pretty solid handle on that period, but it offers a great overview for those who are still learning.

At the end of the museum there’s an incredible 4D movie The Siege at Yorktown. Honestly if you do nothing else in the museum, you need to go watch that movie! It’s the perfect complement to your subsequent visit to Yorktown Battlefield.

The outdoor living history museum at the ARMY is also fascinating. There’s a Continental Army encampment, complete with all the different types of tents you would have seen at the time, numerous types of artillery and a working tobacco farm! We thought the historical interpreters here did an excellent job, particularly those portraying the camp doctors – they answered so many questions and explained everything thoroughly. Every afternoon there’s an artillery demonstration… with audience participation!

In total we spent about two hours checking out the American Revolution Museum at Yorktown, though we would have spent a little longer if we could have.

The final stop on our (and your) adventure through Historic Triangle is Yorktown Battlefield. This site is run by the National Park Service to preserve and educate the public about the battle of Yorktown. If you visited the NPS portion of Historic Jamestowne in the morning, you’ll use the same ticket here (or your America the Beautiful pass). One thing that’s really helpful to know is that the visitors center is only open until 5pm, but once you check in to pay, grab a map and download the audioguide you can visit the grounds until dusk. It offers the most flexibility of any site in the Historic Triangle, which is why I suggest saving it for last.

We skipped the movie and exhibits at the visitors center here, having just come from the larger museum nearby. Most of the visit at Yorktown Battlefield is a self-guided driving tour narrated by a free audioguide app (which also has a section covering the town). The visitors center provides a map and there are signs to direct your route, but we found it a little tricky to follow at times. While the park rangers theoretically offer free walking tours of some parts of the battlefield, unfortunately as of this writing they are virtually non-existent on the schedule (likely due to staffing cuts).

One of the most important places to visit at Yorktown Battlefield is Surrender Field, so named because it was the site of the official surrender by British forces after the battle concluded. The Continental Army confiscated plenty of British artillery and you can see it displayed here.

Real talk time: our family didn’t love most of our visit to Yorktown Battlefield. Unless you are very into battlefield tourism (which some people are), you may not love it either… especially after a full weekend of history tourism! However, all that changed when – on the last stop of the driving tour – we bumped into a local history-loving veteran who has made it his retirement goal to learn all about the battle of Yorktown and teach other people. He came equipped with his own maps and was just waiting for someone to share with! The battlefield came alive and we learned so much from our unexpected 30 minute lesson standing on the top of a British redoubt.

The conclusion I can draw from our experience is that Yorktown Battlefield is much better visited with a knowledgable guide. Unfortunately, NPS isn’t generally providing that at this time and there aren’t many guide options available but I’ll share them with you here (I’ve omitted a third option that’s extremely expensive).

First, you could sign up for a full-day tour that includes Jamestown Settlement, ARMY and Yorktown Battlefield with a guide. The tour includes roundtrip transportation from Williamsburg and follows essentially the same itinerary that our family did. Considering it includes all of your admission tickets and transportation, the price is pretty reasonable. Reviews are excellent.

The other good option is to book a private tour for the battlefield only with this tour guide. He also gets great reviews and charges $90 per hour for your group, with a typical Yorktown tour lasting three hours. Admission is not included, so overall this ends up being a more expensive for most families when you account for buying a separate combo ticket for Jamestown Settlement and ARMY. One caveat: while reviews are excellent, the most recent ones date from 2022.

If time allows, pay a visit to the adjacent town of Yorktown as well. You’ll easily spot the Yorktown Victory Monument, and there are a few other historic buildings dotted around Main Street (though some are closed to the pulic and others are open only sporadically). Yorktown has its own fifes and drums that play once or twice per month as well.

You can wrap up your day with a stroll along pretty little Yorktown Beach and dinner at Water Street Grill.

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How long should you stay in Williamsburg?

In this article I’m sharing our weekend itinerary for Williamsburg and the rest of the Historic Triangle, as I know many families will only be able to spend two days in the area.

That said, I’d recommend allowing a little more time if you can. Colonial Williamsburg itself has some different live performances on different days, and many of the shops and crafters alternate opening days.

For Jamestown and Yorktown, there are actually two sites to visit in each town (as I discussed above). We managed to get to three of the four sites in a single day but we were keeping our eyes on the clock to do it. Spreading those sites out over two days would have given us a much more relaxed pace. Even better, I think you could spend a full day in Colonial Williamsburg, a full day exploring Jamestown (with some pool time or other r&r in the afternoon) and then on a third day spend the morning back in Williamsburg and the afternoon in Yorktown – which even has its own little beach if you find that you have some extra time.

If you have more time to work with, there are some excellent family-friendly options in the area. For example, you could fly into Richmond a day early to visit the Virginia Museum of Fine Arts or the Science Museum of Virginia – both wonderful institutions, and surrounded by plenty more to do in the Museum District. Stay at The Boulevard Inn for historic charm and walkability.

You could also add on a day or two at Virginia Beach, which is just an hour south of Williamsburg (and only 25 minutes from the Norfolk airport). It’s a beautiful beach with a huge boardwalk, plus you can get check out the Cape Henry Lighthouse nearby and enjoy a nature walk at First Landing State Park. Embassy Suites by Hilton Virginia Beach Oceanfront Resort is a great choice for both location and amenities. If you’d rather stay for free, you can redeem points from your Chase Sapphire Preferred for either the Hyatt House or Hyatt Place right on the water.

Of course if you don’t want to go far and your kids are theme parks, you can add on a day at Busch Gardens Williamsburg. It’s a European-themed park (weird but true) with nearly a dozen roller coasters plus other rides and shows. While in the past it was a summer-only option, in recent years they’ve started opening the park year-round for events like Mardi Gras, Halloween, Christmas and more. Nearby Water Country USA is open in the summer and has tons of activities to cool the whole family down if you’ve picked a brutally hot and humid time to visit.

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Plan your family trip to Williamsburg and beyond

There’s so much to do in Virginia with kids, plus you’ll have access to the entire DC area! Check out these additional ideas to plan an amazing trip:

• 6 Colonial Williamsburg “Do’s and Don’ts” For A Perfect Visit
• 10 Best Things to Do in Shenandoah National Park With Kids
• The 5 Best Things To Do In DC With Kids
• 11 Fantastic Day Trips From Baltimore