Virginia is for Families: The perfect three day weekend in Colonial Virginia

Virginia doesn’t get its due for the role it played in American history and for how great that history is to explore with a family, even with little ones. Virginia’s historic triangle of Williamsburg, Jamestown, and Yorktown encompass the first permanent settlement in America, the seat of Colonial power, and the final decisive battle of the American Revolution. All within about half an hour of each other, the three towns and main attractions make for a perfect family trip.


It’s also not just the history here that makes the area worth visiting. The Triangle has recently become home to fantastic restaurants, many situated in historic taverns and inns. There’s also a growing craft brewery scene with some great locations and plenty of awesome brews to find at bars and restaurants. With warm weather pretty much all year, the outdoor spaces on patios and decks are also great. Cornhole is pretty much found everywhere.

The area, especially the big attractions like Williamsburg and Busch Gardens get very busy in the summer. The weather can also be oppressively hot through September, so a visit in the fall can be perfect. The other historic sights like Jamestown and Yorktown don’t get as much tourism either, so they make for a nice reprieve. When visiting the area, here are the best things to do with a long weekend in Virginia.

Day One: Williamsburg

As long as it isn’t a weekend, starting in Colonial Williamsburg is a must. While always crowded, weekdays are less hectic and you’ll still get to see just as much going on. It’s grown a ton since I was a kid and we took family road trips there with tons of live performers, educational talks across the whole town, and tons of taverns for food and drink. Check the schedule online ahead of time for reenactments, especially those with the fife and drums. Tickets are only needed to go into the buildings and for many events, but not to just walk around the town or take part in the reenactments. With fairly steep ticket prices it’s definitely worth skipping the tickets with toddlers who won’t get the most of lectures and learning about Colonial pharmacies and the like. They’ll love just seeing the horse drawn carriages, oxen, other animals, and the costumes. The architecture is worth visiting alone.


While staying in Williamsburg, there’s not better location than Williamsburg Woodlands Hotel and Spa. Right across from the visitor center, it’s easy to just walk right into Colonial Williamsburg. It’s a massive hotel and can be pricey in the high season, but off-peak it’s quite a deal. The included breakfast isn’t high cuisine, but it’s good for families to get a quick and filling bite before a long day exploring the site. There’s even an outside area to eat while feeling less crowded.


From Colonial Williamsburg, it’s a short and pleasant walk down the old main street to the campus of William and Mary, a historic and picturesque campus from Colonial days as well. The campus is rife with beautiful classic buildings, tons of trees, a flower garden, and a picturesque fairy-tale inspired bridge in the middle. A walk around is a great way to continue the connection with America’s historical roots.

Near the campus is a perfect place for a family bite, DoG Street Pub. The front patio has a bunch of seating, perfect for the family to enjoy the weather under an umbrella. Dogs are even allowed, so it’s possible to bring Fido – also allowed on the grounds of both Colonial Williamsburg and William and Mary. The menu is classic pub food – the sandwiches and burgers are awesome – and the beer menu matches with a bunch of great local craft choices. Unlike Busch Gardens it’s far more than just Budweiser here.


A bit further out from the center of town is the incredible Virginia Beer Company. This brewery has an incredible front patio with tons of picnic bench seating and even a few fire pits. Of course there’s also cornhole and sometimes even live bands. The beer list is pretty huge for a brewery with a wide range of options. The big outside area means kids have space to run around without being confined inside and around brewing equipment like so many other breweries. Plus the beer is pretty great.

For dinner, stop in to Hound’s Tale, a dog themed restaurant, of course inside of an old tavern right between William and Mary and Williamsburg. With dog themed décor everywhere including a bulldog statue on one table and dog bowls for snacks like popcorn before the meal, it’s sure to amuse kids and parents alike. It’s not just the décor either, the food and drink are great on the own. There is a kid friendly menu and the food for adults is a great mix of southern comfort, pub food, and modern American cuisine, featuring dishes focused around fresh local veggies and seafood. Of course the beer menu features a ton of local craft brews too.


Day Two: Jamestown

While the breakfast at the hotel is good, there’s always room for a donut. Head over to one of the branches of local favorite Duck Donuts for some of the best donuts and breakfast sandwiches. The bacon on the maple glazed donut is a perfect combination, though you’ll definitely need a knife and fork for it.


The main attraction in Jamestown is of course the historic Jamestown settlement, site of the first permanent settlement in America. Along the water is a recreation of one of the boats that brought colonists over, a church, and some buildings from the settlement. It’s a great place to learn about not only the settlement of the colonies, but also the native people and the interaction between them and the colonists.

Right down the street from Jamestown, tucked along the water at the harbor is Billsburg Brewery. With an awesome location that features a large deck that overlooks the water and another big outside area with picnic tables, food trucks, and of course cornhole, it’s actually a great place to spend part of a day even with a family. The variety of beer makes it perfect for a light brew on a hot day in the sun or a more robust darker one if there’s a chill in the air.

Head back to Williamsburg for the night for food and maybe another drink right next to the hotel at Huzzah’s. The outside patio is the place to be – also more cornhole – and some good food too. If you’re sick of the humidity that somehow exists even in February, there’s a massive inside too. After so much fresh air and sun, it’s ok to head back to the hotel early.


Day Three: Yorktown

Yorktown is often overlooked for it’s importance in the American revolution. While the battle was actually fairly small scale, the surrender of British forces under Cornwallis to a combined Colonial and French force marked the turning point in the Revolution. French Naval superiority was established along the coast and public sentiment in England turned away from continuing the war. Exploring the battlefield is the best way to experience this firsthand. The battlefield is really only walkable in a small part between British fortifications where a bunch of cannons are on display.


Driving along the marked route through the rest of the battlefield is a good way to get a sense of the slow and determined advance of the American and French lines that eventually squeezed the British out. There’s also a massive victory column that celebrates the victory while memorializing the fallen soldiers from the allied side.


Yorktown itself is worth exploring as well, especially the waterfront with a beautiful esplanade that even connects to the battlefield for a longer walk. The town is small, but historic and overlooks the river where the French fleet established control and were able to drive the British away. Town is where Washington and Lafayette met the French commanders and established the strategy that led to victory.

Along the waterfront are several restaurants, but perhaps none has better atmosphere than Riverwalk Landing, a bar and grille with a perfectly pleasant patio right on the water. It’s even covered to get out of the brutal sun. The menu is massive but everything is tasty from the pizzas to the fish tacos. There’s a great beer menu too featured on a huge electronic display that shows temperature, amount remaining, and several other metrics of quality. You’re sure to get a great meal here.


Virginia isn’t just for lovers these days. Families will find a ton to do, even in the relatively small area of the historic triangle. With Colonial Williamsburg, Jamestown, and Yorktown all in short distance from each other, it’s easy to spend a few days exploring the area without having to change accommodations. Even young toddlers will love the variety the area’s attractions that feature historic sights, great food, animals, and lots to see. The kids don’t need to be old enough to study history to enjoy Virginia.

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