An Epic Fall Weekend in Williamsburg, Virginia

In October, we took a weekend trip to Williamsburg, Virginia for a little history and little fun and games. This VA city, just miles from the Chesapeake Bay, is a great weekend trip for families, couples, and solo travelers alike. Below is our 3 day, 2 night itinerary filled with amusement parks, historic towns, wineries, and restaurants. Note: We arrived on a Friday night, so the first “day” is a little light.

Getting There: We drove to Williamsburg from 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 attractions are spread out throughout the city, having a car is virtually a must.

-Day 1-

Check into your hotel, motel, or Airbnb. Because we planned this trip sort of last minute and most places were already full, we ended up staying at a Travelodge just outside of town.
Hit the town for some food. Whether you’re into fast food, upscale dining, or small family owned restaurants, you can find them all here. We had dinner at Fat Tuna Grill & Oyster House and lets just say, add it to your list of stops to make during your visit (provided you enjoy seafood).
Stay out for an after dinner drink or two at DoG Street Pub. This upscale tavern serves craft beers and Brit-inspired comfort food…if you have room for snacks.

-Day 2-

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-

-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 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.

Life-size outdoor recreations of historic structures can be found throughout Historic Jamestowne.

Some original structures are still standing.

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.

Recreations of the three ships, Susan ConstantGodspeed and Discovery, that brought the first permanent settlers to Virginia in 1607 can be explored at Jamestown Settlement.

-Have a late lunch and a wine tasting at Williamsburg Winery just outside of Jamestown. There are two locations on the winery’s grounds to dine at, but we can only speak to one: The Gabriel Archer Tavern. 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.

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