Top 5 Tuesday: Williamsburg, Virginia

Posted by Margaret Anderson in Top 5, Virginia, Williamsburg

CW in the Spring

This week, our travel hot-spot is Williamsburg, Virginia, though climatically speaking, the weather has been far from hot. Yes, the employees at Tripbound do have a fond appreciation for our nation’s history and theme parks, but Williamsburg is also home to Tripbound headquarters. Whether you were born and bred in the ‘Burg, you went to Colonial Williamsburg on a 5th grade field trip, or you can’t find the town on a map, let Tripbound give you the word on Williamsburg.


Top 5: Where To Eat

  • You’re on vacation, of course you can eat a doughnut for breakfast! Duck Donuts offers a warm, delicious, and made to order morning meal. 
  • Contrary to the name, The Cheese Shop is not a popular lunch location for the mice of Williamsburg. Order your sandwich of choice, but be sure to order it with extra house dressing.
  • Here’s some food for thought, dine at Food For Thought. At this restaurant, the good conversation will never cease, and the good food will never cease to amaze.
  • Take a step back in time at Kilwins, an old-fashioned confectionery  selling chocolates, ice cream, and handmade sweets. Trying a little bit of everything is highly recommended!
  • Though the DoG Street Pub is located at the beginning of Duke of Gloucester Street, it is the ideal place to end your evening. The extensive drink menu will cater to everyone from the beer sommelier to the beer amateur.

Top 5: What To Do

  • Just because our town is educational, doesn’t mean it can’t be entertaining too! Travel back in time to Colonial Williamsburg. Interact with the costumed interpreters, march to the Governor’s Palace with the Fife & Drum Corps, and embark on a haunted ghost tour. Your teenager can even Instagram a selfie in the stocks.
  • Experience unique shopping, dining, and special events in Merchant SquareThis area plays host to everything from Saturdaymorning farmer’s markets to live, outdoor music.
  • Ale and beer was a significant staple in the colonial diet, so it should be a significant staple in your Williamsburg diet. A $9 tour of  local brew house Williamsburg AleWerks offers an opportunity to taste the hand-crafted ales, loved by native Virginians and traveling tourists alike.
  • Experience both nature and history at the Eco Discovery Park. Explore Jamestown Island by way of paddle board, canoe, or kayak. For those of you that haven’t grown your sea legs, bikes are also available for rental.
  • The Abby Aldrich Rockefeller Folk Art Museum combines Mrs. Rockefeller’s love of Williamsburg and America folk art. This collection contains painting, sculptures, and objects created by both colonial and contemporary artists.

Top 5: Hometown Tips

  • Monticello Market Place is your one stop shopping center. You need it, want it, or forgot it? Chances are you’ll be able to find it at here.
  • The Kidsburg playground, at Mid County Park will entertain your energetic little one for hours. The  best part, you don’t have to purchase a ticket or day pass to play!
  • San Francisco isn’t the only city with streetcars! The Williamsburg Trolley will take you ’round the town for just $.50 per round trip.
  • Feeling guilty about that Duck Donut now? Walk, run, or bike it off on the Virginia Capital Trail. The route runs all the way from Jamestown to Richmond, so you might as well have that second and third doughnut too.
  • Sometimes you need a vacation from your vacation, (or your family). The men of the group might enjoy an afternoon of golf at the Golden Horseshoe, while the ladies pamper themselves at Nails Uptown.

Top 5: Day Trips

  • Richmond, the capital of the state, was also the capital of the Confederacy. Experience the historical significance of the American Civil War by visiting Monument Avenue or one of the many battlefields.
  • Is the ocean calling your name? Virginia Beach provides the best atmosphere for sunning in the sand and biking on the boardwalk.
  • Charlottesville is home to Monticello and mountains. Tour the home of Thomas Jefferson, and then tour the wineries of the Blue Ridge Mountains.
  • If you can’t get enough history or seafood, make your way to Yorktown. Feed your mind with the significance of the Revolutionary War surrender and feed your stomach with Chesapeake Bay oysters and crabs.
  • Hop on board the Jamestown-Scotland ferry to Surry. In this rural area you’ll find a range of agriculture, from colonial plantations to present-day farms. Click for the ferry schedule

Top 5: Fun Facts

  • Locals affectionately refer to Williamsburg as the ‘Burg, even though 12 other cities in Virginia end in “burg”.
  • Grammy award winner and Grateful Dead band member Bruce Hornsby calls Williamsburg home.
  • Disney’s animated feature film, Pocahontas, is based on the life of the real Native American princess and her interaction with the English settlers at Jamestown.
  • The second-oldest college in America, William & Mary, was founded in Williamsburg in 1692.
  • We hate to break it to you, but colonial impersonators also get their gas at 7-11. Don’t be alarmed if you see “Patrick Henry” fueling up at the gas station on his way home from declaring liberty or death at the Colonial Williamsburg Courthouse.

Banner photos by Tiffany Broadbent Beker.


Ready to book your Williamsburg vacation?

Shop Suite Deals

« Top 5 Tuesday: Reasons to Stay at Star Island | Top 5 Tuesday: End-of-Summer Family Fun »