In October, we took a weekend trip to Williamsburg, Virginia for a little history and a lot fun and games. Located along the state’s coast, just a few miles from the Chesapeake Bay, Williamsburg is the northern point of Virginia’s Historic Triangle with Yorktown and Jamestown to the southeast and southwest respectively.
We both visited with our families as kiddos and on public school fieldtrips with our friends in middle school, but this was our first time exploring the area as adults. And after just a weekend here, it’s safe to say that this region is a great destination for families with kids of all ages, and twenty/thirty-something couples alike, so we’ve put together an ideal itinerary for who are interested in the intersection of history, adventure, and the Coastal VA food and beer scene (which is impressive, to say the least). Below is our three day, two night weekend road trip itinerary filled with amusement parks, historic towns, wineries, breweries, and restaurants.
Getting There: We drove to Williamsburg from Washington, DC, and our trip clocked in at just under 2.5 hours. Our drive was super easy as we spent about 5/8 of the drive on 95 South. Williamsburg is a great road trip destination, and because so many area attractions are spread out throughout the city and surrounding towns, having a car is virtually a must.
That said, if you happen to be an avid biker, you could take the Amtrak from another East Coast city and either carry on your bike or rent one in town. If you plan to take this route, the Virginia Capital Trail, which connects Richmond to Jamestown Settlement, and is dotted with numerous historical sites and businesses as it traverses through the Historic Triangle, offers a beautiful ride. More bike trips in/around Williamsburg can be found here.
Day 1: Sailing and Sipping on the York River
–Check into your hotel, motel, or Airbnb. If you enjoy unique stays and are willing to stay a bit outside of town, we recommend staying at the Williamsburg Winery’s Wedmore Place. This European-style boutique hotel boasts 28 uniquely designed rooms and suites, each designed and decorated based on a different different province. Its located on the grounds of the Williamsburg Winery and your stay comes with a complimentary wine flight.
–Take a Scenic Sunset Sail. We set out with Yorktown Sailing Charters for a sunset cruise along the York River. We went out on the Schooner Alliance II and our tour lasted about two hours. This experience costs $55 and is designed to be a more tranquil experience. So while you shouldn’t expect a tour, our captain and deck hands were super kind and knowledgeable, and happy to chat, point out wildlife, and answer any questions that we had. Chips and beverages (beer, wine, and soda) are available for purchase as well. Sails run daily until November, and tickets can be purchased up to 30 days in advance.
– Have dinner at Yorktown Pub. When our sail ended, and the sun had almost set, we were starving! We somehow had enough self control not to buy any of the Route 11 chips that were being sold on board, and were ready for a feast. Luckily for us, the Yorktown Pub was the perfect place for that, and is located steps away from our disembarkation point on the York River. They serve up delicious pub-style meals as well as fresh, local seafood; We could not recommend their oysters more! They were so good, we ordered an additional half dozen after we’d slurped down our first. Side note: If you can squeeze it into your itinerary, Fat Tuna Grill & Oyster House is another really solid option to consider if you enjoy seafood.
– Grab a nightcap at a local pub or brewery. If you’re not ready to call it a day, there are dozens of local spots to grab a drink.
- DoG Street Pub is an upscale tavern that serves craft beers and Brit-inspired comfort food.
- Precarious Beer Project is a hip brewery located in Williamsburg’s Merchant Square with pinball, pool, tacos, burgers, and of course, local craft beer.
- Virginia Beer Company is another great spot, with outdoor fire pits, a food truck, and a laidback, local vibe.
Day 2: Colonial Williamsburg & Howl-O-Scream
We started our morning at the Williamsburg Farmers Market. This market operates from 8am – 12pm every Saturday and is located in Merchants Square which is adjacent to Colonial Williamsburg. It was the perfect place to grab some fresh, local breakfast.
-We spent the rest of our day at Busch Gardens for their annual Howl-O-Scream Halloween event. Busch Gardens is an amusement park themed around six European countries and has been named one of the nation’s top 10 best amusement parks by USA Today. The park itself is beautiful, and decorating for events like Howl-O-Scream is taken very seriously! We were so impressed with how thoughtfully each village was “dressed up” for Halloween.
Logistics: Operating hours range depending on a variety of circumstances; click here to view the park’s hours and plan accordingly. A day at Busch Gardens involves a lot of walking, so be sure to have on comfortable shoes. You should also plan whether you will pack food, leave the park for lunch, or eat at one of the many themed eateries. Beware of extremely inflated prices within the park, but do know that the food is delicious, and just maybe worth the splurge. We highly recommend the turkey legs from Trappers Smokehouse in New France and the loaded fries at Les Frites in France!
Day 3: History in Virginia’s Historic Triangle
-We devoted this day to visiting all of the living history attractions that Williamsburg is known for. We started the morning at Colonial Williamsburg. Tickets range from $20 – $45 for adults and grant you access to two on-site museums, 40 historic buildings, trade re-enactments, gardens, and free parking. Tickets are required to enter the historic sites and engage with the live programming, but are not needed to walk around the grounds, which is how we choose to explore Colonial Williamsburg.
– We then checked out Historic Jamestowne, which is the original site of the Jamestown colony – the first successful, permanent English settlement in the Americas. While you’re there, be sure to check out the Jamestown Glasshouse where you can watch glass blowers create beautiful pieces as they would have 400 years ago.
Exploring the Historic Jamestown settlement, is also an option. Both Jamestown locations offer a glimpse into early colonial life via artifact museums, costumed interpreters, recreations of the settlement grounds, building ruins, and so much more. Each also have their own entrance fees. Pro tip: If you have a National Park Pass, you’ll receive a discounted rate to Historic Jamestown.
-Have a late lunch and a wine tasting at Williamsburg Winery just outside of Jamestown. The Gabriel Archer Tavern is located on site, and this farm-to-fork restaurant serves impeccable food. We sampled a smattering of things on the lunch menu and have not one bad thing to say about meal, service, or experience. The winery also offers live music on their outdoor pavilion each week and private tasting tours in their wine cellar.
Between soaking in all of the rich history at Colonial Williamsburg and Historic Jamestowne, to getting our adrenaline fix at Busch Gardens, to indulging in the laid-back local foodie scene throughout the entire Historic Triangle, there’s something about Williamsburg that makes it the kind of place that makes you feel like you’ve stepped into a different world while you’re there, and leaves you wanting to plan a return trip as you’re driving home.
