For over 250 years, the holiday season has been one of the most delightful and celebratory times of year in Williamsburg – festive lights line the historic area’s colonial streets, holiday-themed events take place daily around town, and the Williamsburg dining scene is a nightly feast for the senses.
Between Thanksgiving and Christmas, the calendar is full of opportunities to dine, explore, shop, and ring in the holidays with the uniquely colonial-era charm of Williamsburg – it’s all just a short stroll away from our Williamsburg bed and breakfast, located right in the center of the historic district.
Like many historical traditions in Williamsburg, Thanksgiving as a national holiday traces back to the colonial period, when George Washington proclaimed it a nationwide “day of Thanksgiving” in 1789. If you visit over Thanksgiving weekend, you can get a unique and tangible experience of how Thanksgiving became the enshrined holiday we all love and cherish today by attending the 11 am Thanksgiving Proclamation at the Hennage Auditorium (less than a 10-minute stroll from our downtown Williamsburg location) at Colonial Williamsburg. A George Washington interpreter presents his statement on the importance of giving thanks and reflecting on our many blessings. You’ll come away with a renewed appreciation for the holiday, especially in light of that historical moment – when we were only a few years removed from the tumult of the Revolutionary War.
After spending an hour of Thanksgiving morning with Washington, enjoy the crisp early winter afternoon as you walk through the heart of Colonial Williamsburg to the King’s Arms Tavern. From 11 am until 7:30 pm, the history-rich tavern (in operation since 1772) and Williamsburg dining institution serves a Thanksgiving feast, including your choice of starters, entrees, and desserts. The food and pub atmosphere is classic, with everything from the rustic wood interior and pewter candlesticks to the lively staff’s period-appropriate garb setting the scene of an 18th-century Thanksgiving meal, merry and delicious from the first course until the last.
Tap into more holiday festivities throughout Thanksgiving weekend by attending the annual Lighting of the Cressets on the two evenings following Thanksgiving (and again on Dec 22nd and 23rd, if you’re visiting around Christmas). From 6-9 pm, Duke of Gloucester Street comes alive with a ceremonial first winter burning of the Cressets – iron baskets filled with burning wood, the colonial-era version of our modern-day holiday lights. Roaming musicians and carolers provide entertainment while good cheer fills the evening air.
Holiday-themed events are seemingly endless between Thanksgiving and Christmas at Colonial Williamsburg. A Christmas Remembered takes place daily at 11:30 am, when a different historical figure regals the audience with tales of Christmas past, providing insight into how Williamsburg residents celebrated the holiday over two centuries ago. Starting on the Saturday of Thanksgiving weekend and happening at 4 pm every Monday, Thursday, and Saturday through the end of December, A Holiday Medley brings an hour of song, music, and dance, paying homage to all the tried-and-true holiday tunes and traditions.
It all culminates on Christmas Day, when you can celebrate the holiday with a three-course Christmas meal at Christiana Campbell’s Tavern, once frequented by George Washington. Famous for its crabcakes and fish, the Christmas menu will focus on seafood alongside other entrees, sides, and desserts (don’t miss trying the sweet potato muffins). It’s a warm and festive scene with live entertainment from tavern musicians – perfect for feasting and celebrating with loved ones as snow falls and twinkling cressets illuminate the colonial streets outside.
The craft beer scene in Williamsburg is vibrant and exciting, with breweries serving up tasty, award-winning brews and hosting fun-filled events throughout the holiday season. Virginia Beer Company gets into the holiday spirit with specialty beers like Evil Santa, a milk stout made with cinnamon, peppermint, marshmallow, and vanilla, creatively combining all the Christmas flavors in one frosty mug. They also invite local food trucks to set up in their beer garden, a convenient way to try out local eateries as you sip on some of the best beer in town. Nosh Mobile Bistro serves delicious plates like spicy chili garlic chicken and beer-battered fish and chips, while Old City BBQ brings tender brisket, pulled pork, roasted garlic mac and cheese, and smoked stout beans.
Plan to visit during the afternoon of December 9th, 2023, when they host a holiday market at the brewery – sip on a delicious stout or IPA as you shop for unique holiday gifts from various local Virginia peninsula artisans and vendors. Don't forget to explore the Williamsburg Downtown Christmas Market, located just two blocks away, offering a festive array of holiday treasures and treats.
Plan to catch a live show at the historic Kimball Theater during your holiday visit, just two blocks from your Fife and Drum Inn room. Before the show, grab dinner around the corner at DoG Street Pub, where local chef David Everett (a stalwart of the Williamsburg dining scene who also runs the Blue Talon Bistro, one of our favorite Merchants Square restaurants) serves up comfort food like stout chili, corned beef brisket, a variety of burgers (try the lamb), and shepherd’s pie, all extra satisfying on a chilly winter evening.
After your meal, take a leisurely stroll around the block to the Kimball and enjoy the sounds of holiday music. On November 25th, 2023, Bill and the Belles, a Tennessee-based band, will put their country-tinged, rootsy spin on holiday songs. Additionally, mark your calendar for December 2nd, 2023, when the Williamsburg Symphony Orchestra will perform its beloved Holiday Pops program, featuring creative renditions from the timeless holiday music canon.
Following the Holiday Pops show, immerse yourself in the festive atmosphere of Colonial Williamsburg's historic area for the Grand Illumination. This free event features fife and drum performances, storytelling, and fireworks at 7 pm outside the Capitol and Governor's Palace. And right in our building, experience the Williamsburg Downtown Santa event, where Jim Hines, formerly the "Yankee Candle Santa," brings holiday cheer to life.
Stay with us and celebrate the holiday season in Williamsburg with delicious meals, colonial ambiance, and nightly entertainment!