Last Updated on May 15, 2025
Welcome to the charming college town of modern Williamsburg, located in the heart of Virginia. Most people know the town for its colonial heritage and status as part of America’s Historic Triangle. But this quaint city has grown into the 21st century, offering art, culture, shopping, outdoor experiences, and more. Williamsburg is perfect for both tourists and year-round residents, offering a close-knit community and an exceptional quality of life.
Whether you’re vacationing or stay-cationing, Williamsburg offers residents and visitors alike many opportunities to make cherished memories. Here’s our suggested itinerary for a fun-filled weekend in Williamsburg, VA.
Friday evening in Williamsburg, VA
Check into the past
Immerse yourself in Colonial Williamsburg, VA by staying in an historic bed and breakfast for the weekend. There are a number of charming and delightfully welcoming locations from which to choose. For instance, Newport House, Williamsburg’s most historically authentic B&B, was designed in 1756 and is furnished completely in the period. The Fife and Drum Inn is another great option located on the north side of Merchants’ Square. This two-square-block area features some of the best restaurants in the state and more than 40 specialty retail shops, making it the most convenient place to stay downtown.
Dig in at dinner
Old City Barbeque prides itself on the traditional barbecue process by using smokers fueled by hardwood coals. The restaurant focuses on high-quality, locally or sustainably sourced ingredients with a nose-to-tail-inspired menu. Local purveyors are sourced for their integrity and high-quality products, and include Heritage Farm and Anson Mills. Enjoy classic plates of meat and sides. Or branch out with items like the smoked pork belly bahn mi, chopped smoked brisket tacos, and fried Virginia oysters. With so many great options, you’ll be ready to dig in!
Catch a show
The performing arts are alive and well in Williamsburg. The Williamsburg Regional Library system is a standout feature of the community. In addition to books, the library hosts many events each month, including concert series, lectures, and book readings. Other local venues in the area include Williamsburg’s oldest community theater, a world-class symphony, and a multi-purpose arena at William & Mary Hall. Check the local events calendar for concerts, theatrical performances, fairs and festivals, heritage events, and more.
Saturday in Williamsburg, VA
Follow the aroma to breakfast
Start your day in Williamsburg, VA, at Aromas Coffeehouse Bakeshop & Cafe with a delicious full weekend breakfast. The bakeshop roasts their coffee in house, as well as baking their cakes, pies, quiche, cookies, scones, and muffins on site. With gluten free, vegetarian, and vegan specialties, everyone will find something they like. Aromas is also open for lunch and dinner, with great sandwiches, salads, and homemade soups. But their yummy chewy chocolate chip cookies are available any time!
Get fresh at the farmer’s market
If you’re planning to visit Williamsburg over the weekend, you can’t miss their Saturday morning farmers market! More than 1,000 locals gather here each week from March through December to enjoy fresh produce and artisanal products. Williamsburg Farmers Market’s 40+ vendors focus on produce, prepared food, and farm related products grown or made in Virginia. Enjoy live music and more at this open-air market on Merchants’ Square.
Hit the links
Looking for the perfect golf retreat? Golf enthusiasts have come to consider Williamsburg a top golf destination. The area boasts more than a dozen championship courses designed by some of the biggest names in golf, including Arnold Palmer and Jack Nicklaus. At the top of the list are the three courses at Kingsmill Resort & Spa. Play where the pros play on the stunning Pete Dye-designed River Course. Enjoy a round with historic ties on the Arnold Palmer Plantation Course. Or become a member to access the Tom Clark-designed Woods Course, one of America’s top golf courses.
Shop and stroll Merchants’ Square
At its core, Merchants’ Square is a unique destination for shopping and dining. But it’s also so much more. Located adjacent to Colonial Williamsburg’s Historic Area in the heart of downtown, this 18th-century-style retail village features more than 40 shops and restaurants. Specialty shops include Colonial Williamsburg Bookstore, the Cheese Shop & Wine Cellar, and Everything Williamsburg souvenir shop. Shop locally, savor delicious meals, and experience vibrant events, including seasonal concerts, theater, and more.
Take in local art
For those who love art and culture, Williamsburg has an active arts community. The Williamsburg Area Arts Commission hosts several events each month focused on visual arts, literature, music, and theater. Enjoy eighteenth-century exhibits at spots like the American Revolution Museum at Yorktown or Colonial Folk Art Studio & Gallery. Or discover contemporary artists at locations like the award-winning A Touch of Earth or J. Fenton galleries.
If you’re visiting Williamsburg, VA, on the second weekend of the month, don’t miss 2nd Sundays Williamsburg – Art & Music Festivals. These regular street fairs showcase 180+ unique artisans, musicians, street performers, food vendors, and more!
Have a shell of a dinner
The history of York River Oyster Company flows back to the 1960s. But over the last few years, YROC Coastal Bar & Grill has transformed into a true local favorite, being voted “Best Restaurant” in Coastal Virginia in 2024. Today, YROC adds flare to local and coastal favorites on a seasonally rotating menu. Plus, their legendary hand-pressed crushes and unique craft cocktails have made them an East Coast staple. Enjoy indoor and outdoor dining with stunning coastal views.
Toast your time together
Williamsburg is home to a surprising variety of craft beverage options, including breweries, meaderies, wineries, and distilleries. Copper Fox Distillery was the first North American distillery to build a traditional malt floor and kiln since the repeal of Prohibition. And since they opened in 2006, Alewerks Brewing Company has become one of the preeminent breweries in Virginia. Whether you visit for a tour or a tasting, take a moment to drink in your surroundings and toast to a great weekend!
Sunday in Williamsburg, VA
Become a biscuit believer
Old Chickahominy House has been a local favorite for breakfast and lunch since 1955. They are known for their great Southern food, charming gift shop, and cats. But it’s their hot biscuits that made them famous. Be one of the thousands who try them each year, and you’ll see why! Or try a stack of Miss Melinda’s pancakes. Stewie is the gift shop’s current cat mascot. He loves to greet customers, but he’s trained to never enter the restaurant or the kitchen.
Enjoy the great outdoors
It’s easy to embrace the great outdoors around Williamsburg, VA. From biking the iconic Colonial Parkway to hiking and horseback riding off the beaten path, there’s something for every interest. Nature lovers can hang out at one of the city’s 19 parks, which provide walking trails, tennis courts, and picnic shelters. But if you have more time before you head home, we recommend taking advantage of the area’s great scenic waterways. Watersports abound in Williamsburg, with swimming, kayaking/canoeing, fishing, and boating all popular options. Nearby beaches are great spots to soak in the sun, including the dog-friendly beachfront park in Jamestown.
Plan your next trip to Williamsburg
There is far more to do in Williamsburg, VA, than can be fit into a single weekend!
Williamsburg is home to a number of iconic theme parks and attractions that are worthy of their own weekend. From escape rooms to zip lines, it’s easy to appeal to the thrill seeker in everyone. Williamsburg is home to Ripley’s Believe it, or Not!; the eight-acre Go-Karts Plus; and Water Country USA, featuring Virginia’s first water coaster. Busch Gardens® Williamsburg pairs 17th-century charm and 21st-century technology for 130 acres of European-themed family fun. One highlight of the park is the all-new Pantheon®, the world’s fastest multi-launch coaster.
Throughout 2025, Williamsburg is celebrating the 250th anniversary of American independence. Now is the perfect time to explore immersive museums, take fascinating history tours, and enjoy a variety of commemorative events.
And don’t miss Williamsburg’s rich calendar of annual events! There’s no better time to visit than July 4th, when you can celebrate in the spot where American independence was won. The city also pulls out the stops for Juneteenth, their Halloween harvest festival, and winter holiday events.
Spend every weekend in Williamsburg, VA!
For residents of the unique and beautiful area surrounding Williamsburg, it is much more than its history—it is home.
Williamsburg is an independent city that partners with neighboring James City County to offer civic services at a level unusual in such a small area. For instance, residents benefit from top-rated schools through the Williamsburg-James City County Public Schools system, as well as an active library system. Real estate here is equally varied and offers something for everyone. Whether you’re looking for a luxurious condominium or townhouse with all the amenities or a traditional single-family home nestled in a wooded lot, now is the time to find your dream home in this picturesque town full of colonial architecture and scenic landscapes.
Does that sound like the perfect lifestyle for you? Find your dream home in Williamsburg, VA now!
____________________
Allen Tate is the Carolinas’ largest real estate company based on closed sales volume, with more than 70 offices and 1,800 Realtors in the Charlotte, Triad, Triangle, High Country, Highland/Cashiers and Asheville/Mountain regions of North Carolina and the Upstate and Low Country regions of South Carolina. Allen Tate is a partner of Howard Hanna Real Estate, the largest privately held real estate broker in the United States. The full-service real estate company has 480 real estate, mortgage, insurance, title, and escrow service offices and more than 15,000 sales associates and staff across 13 states. For more information, visit www.allentate.com and www.howardhanna.com.
