Insider’s Guide to Williamsburg

Wren Building Wiliam and Mary Williamsburg Virginia

Williamsburg, Virginia is one of the great tourist towns of America. Millions visit each year to experience the recreated colonial town and relive an important era in American history. However, there is much more to Williamsburg than tri-cornered hats, outlet stores and pancake houses. I lived in the ‘Burg full time as a college student and got to know the real hidden treasures of Williamsburg that do indeed make this a great town.

Colonial Alternatives

If you visit Williamsburg, then you will visit the downtown, colonial core. There is no doubt about it and it is after all the reason you are there. But for a fun twist on the colonial theme, explore Duke of Gloucester Street after hours.

Gambols – By day, Josiah Chowning’s Tavern is a typical Williamsburg colonial eatery, offering a great atmosphere and period food. At night though, Chowning’s hosts the always fun, sometimes bawdy gambols. Gambols are games and songs from the 1700s that were popular in taverns at the time. Patrons are encouraged to participate and before long, you will find yourself

Creative Commons License photo credit: cameracarrie

singing along with the rest of the house in raucous songs and limericks. Essentially a colonial bar, Gambol’s is a lot of fun and offers a unique activity in the sometimes stale Colonial Williamsburg experience. There is some light fare, but the main draw are the beers and the fun. The Liebotschäner Cream Ale alone is worth the visit. Gambols usually start around 9:00 pm, but check with the tavern first.

On Duke of Gloucester Street next to Market Square and the Courthouse.

Ghost Tour – Ok, this is a little touristy, but it’s a lot of fun and you learn more about the real history of Williamsburg. The ‘Burg is indeed an ancient city (by American standards) and has been witness to a lot of history, from the earliest days of the country to the present. Along with this long history comes some bizarre and spooky stories. There are several companies offering ghost tours, but the best is the ‘Original Ghosts of Williamsburg Candlelight Tour‘.  The docent leads the group through the Colonial area by candlelight, detailing some of the best ghost stories the town has to offer. It’s a fun experience that is very well priced ($11 per person, 6 & under free) and offers a darker side to a usually saccharine town.

How to Avoid Pancake Houses

Williamsburg has no shortage of dining options. A short drive down Richmond Road will reveal dozens of chain restaurants and pancake houses, drawing the majority of the tourists. If you want to escape this cycle of homogenized meals, be sure to visit what is arguably one of the best BBQ places in the country – Pierce’s Pit BBQ.

Creative Commons License photo credit: The Two Ks

Pierce’s Pit BBQ – Simply put, Pierce’s is a Tidewater institution. Pierce’s began in 1971 as a hole-in-the-wall restaurant that the owners literally built by hand. Now Pierce’s caters to thousands of guests every year, traveling from around the world for this unique BBQ experience.  Located in Lightfoot, VA, just a couple of exit stops away from Williamsburg, Pierce’s is a quick drive up the road from the center of town and well worth the visit. My favorite meal is the J.C. Special: 5 oz. of  pulled pork bar-b-que in “Doc” Pierce’s Original Bar-B-Que Sauce, layered with  homemade slaw, French fries, homemade cookie and a drink all for $7.29.

Visit Pierce’s web site for directions and full menu.

Another dining option is one with which every college student in Williamsburg is familiar – the Delis. Even though these small establishments draw in hundreds of students at night for their cheap beer, during the day they make for affordable and decent eats.

The Delis – Located opposite the College of William of Mary on Scotland Street near the Colonial district, are several small eateries simply called the Delis. Two of my favorites are the Green Leafe and Paul’s Deli. The Green Leafe is a traditional Irish pub with classic fare and beverages. The Leafe tends to be a little more expensive than the other delis, but the food is great and they have 66 beers on tap. Paul’s is a typical deli, offering a wide assortment of burgers, subs and sandwiches. Step back to peruse the menu before ordering, or you may be caught in a Seinfeld Soup Nazi situation. Lining the walls are hundreds of photos and articles illustrating the best of William and Mary athletics through the years.

Unless you want to get caught in a college student drink fest, do not visit the delis at night. Lunch is a perfect time to enjoy the comfort food options here.

Communing with Nature

[stextbox id=”custom” caption=”LandLopers Tip” collapsed=”false” float=”true” align=”right”]The Cheese Shop, on Duke of Gloucester St., sells bread ends and house dressing – perfect for a snack or light lunch.[/stextbox]

Williamsburg can get very hot and very crowded, particularly if you visit during the prime summer months.  Here are two activities that will help you return to your happy place while enjoying some gorgeous scenery.

The Williamsburg Winery – Even though the winery is a very short 10 minute drive from the center of town, it feels like a million miles away. Located on the historic Wessex Hundred property, the winery brings back a tradition of

Creative Commons License photo credit: travit

winemaking to Virginia not seen since Jefferson’s day. The winery started very humbly in the late 1980s and was modeled after a colonial farm. Today the winery is one of the top in the state, producing more than  100,000 cases of wine a year. Visitors may take a tour of the winery and enjoy a tasting of some of their best offerings. For a nice lunch, stop by the Gabriel Archer Tavern and find yourself wondering if this gorgeous vineyard landscape can really be Virginia.

Colonial Parkway – The parkway is a twenty-three mile scenic roadway connecting the Colonial triangle of Jamestown, Williamsburg, and Yorktown. Driving down the parkway is not only an  easy way to reach the area’s top attractions, but is a gorgeous drive as well. Following the James River, there are many areas to stop off to take some pictures and enjoy a picnic lunch.

Even though Williamsburg is a tourist mecca, it is possible to enjoy some unique experiences while at the same time sampling the best the area has to offer.

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By: Matt Long

Matt has a true passion for travel. As someone who has a bad case of the travel bug, Matt travels the world in order to share tips on where to go, what to see and how to experience the best the world has to offer. Also follow Matt on Twitter, Facebook and

One Response

  1. Beverly/@TravelMaestro

    Nice post, Matt. I live in the Tidewater area and frequently enjoy visiting the “locals” parts of Williamsburg. One annual event that is fun for visitors and locals alike is the Grand Illumination at the beginning of the holiday season. All the colonial homes are traditionally decorated with greenery and fruit, fire pots line the streets for warmth, fife and drum corps play, and there are four identical and simultaneous fireworks displays set to music. It draws thousands and is great fun! See you there next year?

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