Feasting and Festivities

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.

Celebrate Thanksgiving with traditions rooted in early American history.

11:00 AM at Hennage Auditorium

• Hear a portrayal of George Washington reading the 1789 Thanksgiving Proclamation.

• A moving moment of gratitude set just after the Revolutionary War.

• Only a short walk from our downtown location.

11:00 AM–7:30 PM

• Enjoy a colonial-style, multicourse Thanksgiving meal.

• Rustic décor, candlelit ambiance, and costumed staff recreate an authentic 18th-century dining experience.

• A perfect mix of history, comfort, and holiday cheer.

The Friday & Saturday after Thanksgiving (and again Dec 22–23)

• Duke of Gloucester Street lights up from 6–9 PM.

• Iron cressets filled with burning wood illuminate the colonial streets.

• Carolers, musicians, and lively crowds create one of the most enchanting scenes of the season.

Daily at 11:30 AM

• Meet a different colonial figure each day.

• Hear stories of how Christmas was celebrated more than 200 years ago.

4:00 PM every Monday, Thursday, and Saturday (starting Thanksgiving weekend)

• An hour of festive music, dance, and song.

• A tribute to beloved Christmas traditions through an 18th-century lens.

Celebrate Christmas with a historic feast in one of Williamsburg’s most storied taverns.

• Known for seafood — especially the famous crabcakes.

• Enjoy a three-course holiday meal, seasonal sides, and desserts (the sweet potato muffins are a must!).

• Live music fills the tavern with warmth and joy as you dine.

Need more dining suggestions? Here are some of the best places to eat in Williamsburg. 

• Seasonal brews like the beloved “Evil Santa” milk stout.

• Rotating food trucks serving mac & cheese, brisket, fish & chips, and other hearty winter favorites.

• Early December Holiday Market: local artisans, handmade gifts, festive drinks, and relaxed afternoon shopping.

• Just two blocks from your Fife and Drum Inn room.

• A treasure-trove of holiday gifts, décor, and locally made treats.

• Perfect for finding unique, meaningful presents.

 

• Steps away from your room at the inn.

• Start your evening with comforting pub dishes at DoG Street Pub — burgers, shepherd’s pie, chili, and more.

• Enjoy holiday performances including the Williamsburg Symphony Orchestra’s annual Holiday Pops, a favorite local tradition.

• After the concert, head into the Historic Area for fireworks and festivities.

• Fife and drum performances, storytelling, and brilliant fireworks at the Capitol and Governor’s Palace.

• A free event that draws visitors and locals alike.

• Hosted right in our building.

• Featuring the beloved Jim Hines (formerly “Yankee Candle Santa”).

• A charming stop for families visiting during the season.

Choosing our inn for your holiday stay means:

• A short walk to Colonial Williamsburg, Merchants Square, and local dining.

• Warm, inviting rooms — perfect for relaxing after candlelit strolls and festive events.

• Daily excitement just steps outside your door: markets, music, taverns, and holiday celebrations.

• A blend of history, comfort, and authentic Williamsburg charm.

 

A few tips to make the most of your holiday trip:

• Check event times: Schedules vary year to year — always confirm before your visit.

• Book early: Taverns and holiday shows sell out quickly.

• Dress for winter: Layers and walking shoes recommended for the Historic Area.

• Plan to walk: The magic of Williamsburg is best experienced on foot.

Stay with us and celebrate the holiday season in Williamsburg with delicious meals, colonial ambiance, and nightly entertainment!