The LandLopers Guide To Williamsburg, Virginia

By Matt Long,

I went to college in the colonial town of Williamsburg, Virginia; an odd place for a college student, no doubt. I also spent most of my breaks in town, working and getting ahead on studies and through that experience I got to know the town as a local instead of just a student. Those years also instilled a fierce love of this quirky community that I still have today. I recently returned to this popular tourist destination and thought I’d share an insider’s view on what to see and do through a personal guide to Williamsburg, Virginia. 


What To Do


Fall in Williamsburg Virginia
Photo by Bart CC BY 

We have to start with the obvious reason why millions visit every year – the colonial stuff. Jamestown is just a few miles away and was the first permanent settlement by colonialists in the modern-day United States. So Williamsburg is an old town, very old by American standards, and at one time was the capital of the Virginia Colony and home to the first form of democracy on the continent, the House of Burgesses. Today Colonial Williamsburg is a reconstructed look at what Williamsburg looked like a few centuries ago. Using the original buildings themselves whenever possible and rebuilding others on the exact sites where they once stood, a visit to Colonial Williamsburg really is a very accurate representation of 17th and 18th century American life. As you walk down the mile-long Duke of Gloucester Street (or DoG Street, as locals call it) you’ll notice scores of people in period dress, doing chores or leading groups. This is all a part of the Colonial Williamsburg experience and these actors bring that era back to life.

Hats in the D of G Market Williamsbutg, VAPhoto by Ron Cogswell CC BY 

Certainly suitable for families, Colonial Williamsburg is a great destination for adults too. In the evenings, one of the colonial restaurants, called taverns, turns into Gambols – a colonial pub. Head there at night for huge beers, plenty of snacks, period music and games. It’s actually a lot of fun and a must-do experience. The Kings Arms Tavern is also an important place to eat at least one evening of your trip, bringing to the table authentic colonial recipes to a fun, fine dining experience.

Of course there’s a lot more to Williamsburg than just the colonial part, and one of the best things to do is actually adjacent to the colonial areas. The College of William and Mary was chartered in 1693, making it the 2nd oldest university in the United States. Notable students include Thomas Jefferson, George Washington, James Madison and more recently Glenn Close and Jon Stewart! The oldest part of campus is known as the Ancient Campus and includes the original three buildings of the College, including one designed by famed-architect Sir Christopher Wren. Bring a picnic lunch from the Cheese Shop restaurant and eat it on the Sunken Gardens, the expansive green space in the middle of campus. Watch as students play Frisbee or just relax in this tranquil part of the university.


Where To Eat


 Pancakes by Laura D'Alessandro CC BY
Photo by Laura D’Alessandro CC BY 

Since Williamsburg is a major tourist destination, there is no shortage of great places to eat. To start the day, be sure to visit one of the town’s many pancake houses. I’ve never quite understood why Williamsburg has so many, but it does and they’re all excellent. For lunch and dinner, be sure to spend some time in the historic downtown of the town.

The Cheese Shop Williamsburg
Photo by The Cheese Shop Facebook 

The Cheese Shop has been popular amongst locals and students for decades and in addition to gourmet foods and sandwiches, they make their famous Bread Ends and House: a bag of bread loaf ends with the café’s signature House dressing. Believe me, it’s amazing. As I mentioned, be sure to make reservations at one of the classic colonial taverns in town at least one evening. It’s a little corny, but the food is excellent and the experience really is fun.

cheeseplate_bedfordcheeseshop
Photo by Bedford Cheese House Facebook 

If you have a sweet tooth, then dessert and a nightcap at The Trellis Restaurant is something you’ll really enjoy. Way back in the late 80s they invented their signature Death By Chocolate, a dessert that has since been copied all around the world.

The Trellis Restaurant Dessert
Photo by The Trellis Bar and Grill Facebook 

If you want to feel like a student, then stop by one of the so-called delis. The row of small delis/restaurants next to the heart of the campus feature great sandwiches and entrees along with a comprehensive drink selection, as you’d expect for a popular college haunt. Lunch is the best time to grab a bite to eat and in the evenings, especially Thursday through Saturday, be prepared for massive crowds as most of the university’s 5,000 undergrads all try to crowd into one of these three delis.

New York Deli Williamsburg A Currell CCBY
Photo by A. Currell CC BY 

I’m a BBQ fanatic and the best in the country, at least in my opinion, is a very short drive from downtown Williamsburg in a neighboring community called Lightfoot. For decades, Pierce’s Pitt BBQ has been delighting those in the know with simple but amazing BBQ plates. Chicken, pulled pork and more with all of the fixings, this is an experience and not just a meal. Look for the restaurant’s iconic bright orange roof from the highway.


Non-Colonial Activities


Williamsburg Winery
Photo by Williamsburg Winery Facebook

While you may initially visit for the colonial charm of the town, there’s a lot more to Williamsburg than just tri-cornered hatsThe Williamsburg Winery started life in the late 80s and since then has become one of the best wineries in the state and even the country. Set on acres of rolling vineyards, even though it’s a short drive from the center of town, it feels like you’ve traveled to the middle of the French countryside. Go on the winery tour, try a selection of their fine wines and even enjoy a leisurely lunch at their tavern.

Busch Gardens Stephen Dettling CC BY
Photo by Stephen Dettling CC BY 

If you’re more into action, then Busch Gardens is for you. This European-inspired theme park has everything you’d want for a day of thrills: roller coasters, flume rides and many other fun-filled experiences. There are also shows and pretty good food, so plan on spending the day. Not far from Busch Gardens you’ll also find the James River, a beautiful spot to just relax or go on a boat ride.

Ok, I have to return to just a couple of more colonial activities: Jamestown and the Historic Triangle are well worth exploring. This truly is the birthplace of America as we know it, and learning more about the early settlements is fun for folks of all ages. Along the way be sure to stop off at one of the riverside plantations to learn more about the well-heeled of the 17th and 18th centuries and what life was like in antebellum Virginia.

Williamsburg is a fun place to visit for a weekend or longer, just make sure you take advantage of everything the town has to offer!


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Cover image Aaron Burden, Unsplash