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Old-World Charm, Carriage Rides, and Seafood: Why Williamsburg, Virginia Is the Perfect Winter Getaway

Insider Guides
by Hayley Hutson Feb 3, 2023

As the centerpiece of Virginia’s Historic Triangle, Williamsburg is known as the heart of America’s colonial preservation. While millions of visitors flock to the city each year to experience the world’s largest living history museum, it’s also grown into a vibrant tourist destination for artisans, nature lovers, history buffs, anyone who appreciates delicious food.

Best things to do in Williamsburg in the Winter

Williamsburg is home to a wide array of exciting things to do in any season for all types of travelers. During the winter months, there are a few activities you won’t want to miss.

Colonial Williamsburg walking tours

Before Richmond took over as Virginia’s capital in 1780, Williamsburg was the political center of America’s largest and most influential colony. With such a rich depth of history and culture, a guided walking tour is the best way to learn about everything you won’t find in a textbook. On the tours, you’ll hear first-hand about fascinating local legends, scandals, and the ghosts that lurk around to this day. Fun fact: Colonial Williamsburg is the birthplace of “rock, paper, scissors” and the home where it was invented (which still stands) is believed to be the most haunted house on the Eastern Seaboard.

Colonial Williamsburg Walking Tour: Various starting locations

Historic Jamestowne

Photo: Jamestown Rediscovery

Located just 15 minutes from Colonial Williamsburg, Historic Jamestowne was the first successful English colony in North America and now serves as a dramatic reminder of how our nation got its start. You can chat with living history interpreters at the Black Smith’s Forge, explore the exhibits inside Memorial Church, and witness excavation in action at the archaearium. Over the last 25 years, archaeologists have excavated around 3 million artifacts from the original settlement, many of which can be viewed at the on-site museum.

Historic Jamestowne: Start at the visitor center located at 1368 Colonial Pkwy Jamestown, VA 23081

Carriage rides

It’s near impossible to walk through Colonial Williamsburg without seeing a few horse-drawn carriages trotting about. There’s something truly special about experiencing the sights and sounds as they did back in the 18th century, so it’s no surprise that booking a carriage ride is one of the most popular things to do in Williamsburg. You can purchase a same-day ticket at any Colonial Williamsburg ticketing location, but keep in mind that tickets sell out quick so you’ll want to arrive early. Virginia is quite chilly in winter, so be sure to bundle up so you can enjoy the leisurely ride without freezing your tail off.

Carriage wagon rides: Various starting locations

Historic Yorktown Village

Yorktown is known for its waterfront charm, famous battles, and year-round events. No visit to the Historic Triangle would be complete with stopping by Yorktown for at least a few hours to explore the area’s historic sights and the local shops found in Riverwalk Landing. In 2022, Yorktown hosted its first-ever nighttime Christmas Market on Historic Main Street. An enchanted evening here boasts live music, local vendors, food trucks, ice carvings, roasted chestnuts, and a kids’ craft area. Yorktown Market Days run February and March for the winter market.

Historic Yorktown: Start at the market, located at 401 Water St, Yorktown, VA 23690

Visit a meadery

Williamsburg boasts several breweries, wineries, and distilleries to explore, but I highly recommend channeling your inner colonist and adding a meadery visit to your travel itinerary. After all, mead is what all the cool kids (yes, literally kids, but also adults too) were sipping back in the 1700s. When I visited the award-winning Silver Hand Meadery, I opted for a tasting experience to learn more about the fermented honey-based wine and its origins. The “Dream by the Fire” mead, a three-honey blend made with Virginia apple cider, was my favorite because it tasted like Christmas in a cup. When I told my tasting guide that it would make the perfect holiday candle scent, he surprised me by showing me their handmade candles inspired by the mead flavors.

Silver Hand Meadery: 224 Monticello Ave, Williamsburg, VA 23185

Where to eat in Williamsburg, Virginia

Fat Canary

Set in the heart of Colonial Williamsburg, Fat Canary is an upscale American bistro and one of the most popular restaurants in town. The atmosphere is cozy, the servers are warm and welcoming, and the dishes are beyond impressive. Standouts include locally-sourced oysters, lobster fettuccine appetizer, pan-seared duck breast, and sea scallops with lemon basil risotto.

Fat Canary: 410 W Duke of Gloucester St, Williamsburg, VA 23185

Cochon on 2nd

Cochon on 2nd exists at the intersection of fine dining and small town charm. This intimate restaurant is the perfect place to wind down after a long day with a glass of wine and a fantastic meal. Reservations are highly advised (even if you plan on sitting at the bar) because this is a local hotspot and will likely be packed. Trust me, the fantastic food and exceptional service make Cochon on 2nd well worth a wait. While you can’t go wrong with anything on the menu, the wagyu burger particularly stands out.

Cochon on 2nd: 311 -106 2nd St, Williamsburg, VA 23185

Le Yaca

Le Yaca serves Traditional French cuisine in a refined dining room setting. The restaurant itself is stunning, from the contemporary light fixtures and brick-lined bar to the heated patio. You can book a reservation for brunch, lunch, or dinner. I dined here for the prix fixe brunch and was absolutely stuffed (in the best way) by the end. I’m still dreaming about those chocolate croissants and the seafood eggs benedict.

Le Yaca: 1430 High St, Williamsburg, VA 23188

La Piazza

After capping off a long day of exploring with the Grand Illumination firework display over the Governor’s Palace (once the home of President Thomas Jefferson), I had worked up quite an appetite. Luckily, La Piazza is located right down the street and serves up northern Italian dishes in portion sizes fit for a king. On the advice of my server, I ordered the meatball appetizer and Tortiglioni alla Bolognese — both were bursting with the delicious, savory flavors I had been craving.

La Piazza: 403 W Duke of Gloucester St, Williamsburg, VA 23185

Second Street American Bistro

If you’re on the hunt for comfort food, Second Street is an ideal choice. This upscale-casual bistro offers a welcoming atmosphere, friendly service, and a hearty menu that serves up American classics with unique culinary twists. The flatbread pizzas are divine, as is the bacon and blue cheese burger. The menu is the same for lunch and dinner, but the brunch menu is only available on Sundays.

Second Street American Bistro: 140 2nd St, Williamsburg, VA 23185


Saladworks opened in Colonial Williamsburg in 2022 and has quickly become a lunchtime favorite for tourists, locals, and William & Mary students looking to venture off campus. The laidback quick-service eatery features an assortment of soups, salads, wraps, and paninis. If you love a good panini, do yourself a favor and order the chipotle chicken ‘n bacon panini.

Saladworks: 110 N Henry St, Williamsburg, VA 23185

Free Range Juice

Whether you’re looking to support your immunity during the colder months or want to kickstart your day with an energy boost, Free Range Juice has just what you need. I’m not a big breakfast person, so I loved starting my morning at this cozy juice bar with a freshly made smoothie or cold-pressed juice. My partner was sick at the time, so he definitely appreciated the wellness shots I brought back for him.

Free Range Juice: 410 Lightfoot Rd Ste G, Williamsburg, VA 23188

Where to Stay in Williamsburg

We hope you love the spaces and stays we recommend! Just so you know, Matador may collect a small commission from the links on this page if you decide to book a stay. Listed prices are accurate as of the time of publication.

Williamsburg Lodge

Located in the heart of Colonial Williamsburg, the Williamsburg Lodge harmoniously blends 18th century style with modern comforts like a full-service spa and high-speed WiFi for an elegant yet homey stay. From the moment you set foot in the lobby, the attention to detail and homage to colonial history is unmistakable. The property itself is massive and features several buildings with rooms that range from Chippendale-style deluxe rooms to spacious suites dripping in Southern elegance. If you have time for a little self-care, walk over to the on-site Spa of Colonial Williamsburg for a revitalizing spa treatment. Pro tip: No matter which service you book, arrive at least an hour early to take advantage of indulgent amenities like the steam room and lounge.

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Williamsburg Inn

To experience the height of luxury in historic Williamsburg, the Williamsburg Inn is a stellar choice. The hotel features elegant guestrooms designed in Regency style, upscale amenities, an in-house restaurant, and 45 holes of manicured golf courses. As the only Forbes Travel Guide Five-Star rated resort in the Historic Triangle, the Williamsburg Inn is a popular choice among the luxury travel sector.

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Hampton Inn & Suites Williamsburg

If you’re traveling on a budget, Hampton Inn & Suites is a great choice located just two miles from Colonial Williamsburg. The pet-friendly hotel features well-appointed rooms and suites, free parking, a fitness center, and daily breakfast. Visiting with children? You can take advantage of one of the hotel’s connecting rooms.

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How to get to Williamsburg, Virginia

When planning a trip to Williamsburg, it’s important to remember that there are no airports in the city itself. However, there are three airports within a one-hour drive: Newport News/Williamsburg International Airport (PHF) located 17 miles south, Norfolk International Airport (ORF) located 45 miles southeast, and Richmond International Airport (RIC) located 45 miles northwest.

Once there, Colonial Williamsburg is incredibly easy to walk around in. That said, the city of Williamsburg is quite large and requires some type of transportation. You can get around by taxi, rideshare, public bus, trolley, or car. Public transit is a great option if you don’t have a car and plan on staying in Williamsburg, but I would recommend bringing a vehicle if you want to explore the other parts of the Historic Triangle.

The best way to get to Williamsburg is by flying to one of the nearby airports and renting a car to get into the city. While public transportation is available via trolley or public bus, you’ll want to have a vehicle to make the most out of your time in the Historic Triangle.

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