Williamsburg, Virginia: a historic gem with modern-day appeal

Details in this story were updated in September 2024.

For many Americans, Thanksgiving is synonymous with Plymouth, Massachusetts. But we’ve got news for you: The home of the true original Thanksgiving is located many miles south in the Williamsburg, Virginia area. More than a year before the Pilgrims set foot in New England, a group of English settlers landed on the shores of the James River in 1619. Their ship’s captain declared that their arrival must “be yearly and perpetually kept holy as a day of Thanksgiving.”

So what better place to head for the holidays than Williamsburg, which—along with Jamestown and Yorktown—is known as America’s Historic Triangle? It’s the ideal destination for a long weekend getaway, thanks to its cornucopia of food, history, and fun. Just ask Robby Willey, who went to the College of William & Mary and later returned to open The Virginia Beer Company with one of his university friends. “As we discovered Williamsburg as adults, we started to fall in love with the combination of the small town vibe and some of the bigger city aspects,” says Willey. “It’s got an amazing culinary scene and so much access to history and entertainment with Colonial Williamsburg, Jamestown, Yorktown, and Busch Gardens."

Landon Stulen is another local who shares that passion. He pretty much grew up at Colonial Williamsburg: He was in the Fifes and Drums corps as a kid and later took over this historic marching band. According to Stulen, the Greater Williamsburg region does an excellent job of balancing past and present. “There’s no other spot in the world where you can be totally engulfed in Revolutionary history and also experience a new, young modern energy,” says Stulen.

We can’t think of a better reason to give thanks, so let’s head to Williamsburg to start the holiday season off right.

Golfers. Families. Sweethearts. Foodies. History buffs. Nature lovers. There’s literally something for everyone at this sprawling 3,900-acre resort on the banks of the James River. Here, you don’t just stay in a basic hotel room: The accommodations are massive condos with full kitchens, ranging from one-bedroom apartments to spacious riverfront cottages to the four-bedroom Estate, complete with an infinity pool. Explore the bike trails. Spot bald eagles roosting in the trees. Float along the lazy river or splash around in one of the three pools (inside and out). Rent waverunners at the full-service marina. Check out the old Civil War site, overlooking one of the championship golf courses. The perfect end to the day: devouring local oysters at the James Landing Grille as the sun sets over the river.

Honorable hotel mentions

It doesn’t get more picture perfect than the Williamsburg Inn, especially during the holidays when the Regency-style property is transformed into a twinkling winter wonderland.

Immerse yourself in history with a stay in one of the 18th century-style houses—complete with canopy beds and working fireplaces—set right in the heart of Colonial Williamsburg.

A pair of friendly innkeepers run this boutique B&B in the center of town that defines Southern charm.

Kids will love this action-packed resort with an indoor waterpark, a bowling alley, a ropes course, themed suites, and more.

This condo resort is built around a manor house dating to 1735 and is surrounded by hundreds of acres of woodland.

This area is fast becoming a foodie powerhouse. “It’s always been a melting pot, thanks to immigrants who originally came from England and, later, from all over the world,” says Willey. “You see the history of how the Americas were founded in the culinary offerings—with some people interested in nostalgia and others bringing new flavors to town.”

Shorty’s Diner - “Williamsburg has a handful of retro diners and this spot has been a mainstay for as long as I can remember,” says Willey. Expect oversized pancakes, huge omelets, and decadent biscuits and gravy.

Five Forks Cafe - Another traditional diner that’s known for its overflowing plates. The fan favorite: corn cakes topped with honey butter.

Tipsy Beans Cafe - Want a more sophisticated breakfast scene? Tipsy Beans is the place to find dishes like avocado toast and crab cake eggs Benedict.

The Cheese Shop - It’s more than just cheese at this not-to-be-missed spot in Merchant’s Square. Be sure to try a sandwich topped with the cult-like house dressing (a secret blend that is also sold by the bottle).

Precarious Beer Hall - Just steps from Colonial Williamsburg is this modern-day taco bar and beer hall with arcade games and pinball machines that appeal to both kids and grownups.

Bellissimo Pizza Cafe - “Traditional New York-style pizza in a little strip mall,” says Willey. “It’s constantly slammed. They do a barbeque chicken pie and a pickle pizza that’s renowned around here.”

Casa Pearl - “A small taco and oyster restaurant—the chef brought some tastes of Charleston, South Carolina with him,” says Willey.

Second Street Bistro - Americana with a dash of international fusion, plus great cocktails. “If you’re a restaurant that’s survived 20-plus years and a pandemic, you’re doing a lot of things right,” says Willey.

Old City Barbecue - “This is a coming-of-age story,” says Willey. When Willey came back to Williamsburg, Old City’s founder, Vernon Geddy, was working in real estate and doing home-smoked BBQ on the side. Lo and behold, Vernon Geddy became a chef. "Now he serves our beers at his restaurant, and we host his food truck regularly at our brewery,” says Willey.

Green Leafe Cafe - This is one of the town’s famous “delis,” which is the name for the local college bars that also serve simple pub dishes. “The Green Leafe is where my business partner and I discovered our love of craft beer,” says Willey. “It’s got a dark, British pub vibe.”

Amber Ox Public House - A gastropub known for its fresh, locally sourced ingredients.

Oceans & Ale - The place for great seafood and an all-you-can eat crab night. “Don’t miss the seafood spring rolls,” says Stulen.

La Tienda Tapas Bar & Market - An old house has been retrofitted and turned into a restaurant with Spanish tapas and a showroom for wines, meats, olives, and other imports. “It’s completely different from anything else in the greater Williamsburg area,” says Willey.

Masala Craft - “A family-owned Indian craft kitchen with small-batch dishes and an Indian-themed cocktail bar,” says Willey.

Le Yaca - “This French restaurant is one of my favorites in Williamsburg — the food here is absolutely amazing,” says Stulen. Don’t miss the Grand Marnier soufflé.

Cochon On 2nd - “A warm and cozy high-end restaurant where everything hits the right spot in terms of the flavor profile. It’s some of the best salmon I’ve ever had,” says Willey.

Kings Arms Tavern - At this reproduction of a 1772 tavern in Colonial Williamsburg, everything is true to the time period. “It’s a cool experience to be served by folks who are dressed up and speaking in Colonial fashion and serving dishes like game pie,” says Willey.

Fat Canary - This tiny high-end bistro always has a wait. (A tip: The Cheese Shop transformed its wine cellar into a speakeasy-style spot where you can order dishes from the Fat Canary).

The Virginia Beer Company - This microbrewery has a taproom and beer garden in Williamsburg’s up-and-coming Edge District. Active philanthropy is at the heart of the business, and the beer is damn good, too. During the holidays, the Evil Santa—a creamy dark beer with cinnamon nutmeg and allspice—is a cult favorite.

Billsburg Brewery - This brewery has an ideal location at the Jamestown Marina, overlooking the water. “I love the atmosphere, and we sell their Kingsmill lager at the resort,” says Stulen.

8 Shires Coloniale Distillery - A Colonial-themed distillery where you can taste rum as it was meant to be enjoyed in the 1800s.

Copper Fox Distillery - A modern, speakeasy-style distillery in an old motel. Head through the secret bookcase for flights and cocktails. “It’s an off-the-beaten-path spot in Williamsburg,” says Willey.

Silver Hand Meadery - Learn how mead (a honey wine) is made at this forward-thinking spot. “They’ve done some carbonated meads, and they are cultivating their own honey as well,” says Willey.

Williamsburg Winery - A massive winery on a 300-acre farm with tastings and a vibe that is straight out of old Europe.

The largest living museum in the country, Colonial Williamsburg is an historic gem where actors in period costume stroll the streets, work at the stores, and reenact daily life from the Colonial era. Navigating a place like this can be challenging when you only have a weekend, so we got Robert Currie, Colonial Williamsburg’s director of entertainment, to share the five things not to miss.

1. “Take a carriage ride throughout the historic district. Getting a look at this 18th century town from a horse-drawn carriage is a wonderful experience and the drivers are really knowledgeable. But the availability is limited, so when you’re booking your admission tickets and your hotel, you need to book this, too.”

2. “Check out the historic trades—but make sure you find out what’s open because not everything is open every day. The most popular are the blacksmith, the tinsmith, and the armory.”

3. “Encounter the Nation Builders, who portray real figures that made significant contributions to the American story. I personally love James Madison, but they’re all great to see, from Thomas Jefferson to the Marquis de La Fayette.”

4. “Set aside an hour and a half to visit the two onsite art museums—the DeWitt Wallace Decorative Arts Museum and the Abby Aldrich Rockefeller Folk Art Museum—which recently had a $40 million expansion. It’s something to do later in the day, since they’re open a little later than the historic district.”

5. “Stick around after 5 p.m. Don’t miss a pirate trial in the evening at the Capitol, which is a trial based on actual events that took place in the Williamsburg area. Another great experience: a music ensemble in the ballroom of the Governor’s Palace.”

Roots run deep in these parts. After you’ve strolled through history in Colonial Williamsburg, here are two other spots to check out.

Jamestown Settlement - Learn about the founding of America in recreated settings including a Paspahegh town, three ships from 1607, and an old fort.

American Revolution Museum at Yorktown - Another living-history museum where visitors can experience a Continental Army encampment and Revolution-era farm.

When you’re ready to enter the modern era, the Greater Williamsburg area provides plenty of entertainment.

Busch Gardens - From the Anheuser-Busch family comes this epic amusement park with seven world-class roller coasters, plus a Sesame Street area and Virginia’s largest water park. No surprise: The beer offerings are pretty spectacular. The place comes alive during the holidays with over 10 million twinkling lights, a Santa Village, an ice skating show, and more.

Colonial Parkway - Don’t miss a drive along this 23-mile tree-lined scenic roadway that connects Williamsburg, Yorktown, and Jamestown.

Spoke + Art Provisions - A cutting-edge art gallery in the center of town.

Sweethaven Lavender Farm in James City - Visit for the Christmas festival over the weekend of December 3 and bookmark this magical place for a future visit: Its lavender fields blossom from May through July.