2 Day Trip to Colonial Williamsburg, VA

We spent two days soaking up the history and charm of Colonial Williamsburg while staying at the wonderful Club Wyndham Kingsgate. The resort had plenty of space and fun stuff for the kids, making it a great home base for exploring the old streets, watching reenactments, and grabbing some tasty local eats. It was the perfect mix of history and family fun! Below is how we spent our time, plus some helpful tips!

Day 1 – Stepping Back in Time

We started our family adventure with a short drive to Colonial Williamsburg, Virginia—an easy trip that still felt like we’d traveled centuries into the past. We had purchased our tickets online ahead of time, which made entering the historic area quick and easy.

From the visitor entrance, we strolled along the scenic path into the heart of the Historic Area, where costumed interpreters brought the 18th century to life. We watched skilled artisans practicing traditional trades, from blacksmithing to weaving, each eager to share their craft and answer curious questions.

One of the highlights of the morning was the court trial performance. Audience members were invited to take part as townspeople and jurors, adding a fun, interactive twist. Later, we gathered in the crowd to hear some of America’s earliest presidents—portrayed by talented actors—field questions about life, politics, and the challenges of a new nation. It was both entertaining and surprisingly thought-provoking.

When our stomachs started to rumble, we headed over to Merchants Square, just a short walk from the historic area. We chose Mellow Mushroom for lunch—a colorful, welcoming spot that was perfect for families. We ordered a couple of pizzas for the table, and they were a hit with both kids and adults. We were glad we arrived just before 12:30, because by then a line had already formed at the door.

On our way out of the Historic Area we stopped at the Governor's Mansion. We took the guided tour which was a highlight for the whole family. The kids especially loved walking through the gardens and getting lost in the maze—it was a fun, hands-on way to experience history.

The combination of rich history, interactive performances, and a hearty lunch made our first day in Colonial Williamsburg both educational and enjoyable. It set the perfect tone for the rest of our trip.

Tips for Visiting Colonial Williamsburg

1. Wear comfy clothes – Once you get into the Historic Area, there’s a lot of walking. Comfortable shoes are a must.

2. Bring a smaller cooler for snacks – There are a few sit-down restaurants in the Historic Area, but if that’s not your style, Merchants Square is a 10–15 minute walk. We recommend planning a couple of hours in the Historic Area, walking to Merchants Square for a meal, and then heading back.

3. Look for the flags – When strolling down the cobblestone streets, houses with flags outside are open for you to explore! Sometimes the doors are closed because tradespeople are working inside, but you’re still welcome to go in and look around.

Day 2 – Merchants Square & Pool Time

We began our Sunday morning with a stroll through Merchants Square, where the weekly farmers market was in full swing. It was the perfect way to mingle with locals and sample regional flavors. We indulged in fruity popsicles, fresh-squeezed lemonade, and warm donuts—admittedly a lot of sugar to start the day!

After wandering the market, we did a little souvenir shopping in the square and then settled at the outdoor tables to people-watch while the kids played and ran around. It was a relaxed, cheerful way to spend the morning.

By midday, we headed back to the hotel for an afternoon of swimming, giving everyone a chance to cool off and recharge.

Where We Stayed – Club Wyndham Kingsgate

We stayed at the Club Wyndham Kingsgate, which turned out to be the perfect spot for our large family. Our suite was spacious, with two bedrooms, a living and dining area, and a full kitchen—almost too good for the price and tempting us to stay even longer!

The resort offered endless ways to keep the kids entertained. We played a round of mini-golf, swam in the pool, and cooled off with icees by the water. Inside, the game room was a huge hit, featuring arcade games and pool tables. Outdoors, we enjoyed lawn games like cornhole and even tried axe throwing. Honestly, we could have planned an entire day just enjoying the resort itself.

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Have More Time? Here’s What’s on Our Next-Trip List

We didn’t get to explore the other two corners of the Historic Triangle this time, but they’re high on our list for next time.

• Jamestown Settlement – Step back into the 1600s at the recreated ships, fort, and Powhatan Indian village. We’d love to board the Susan Constant replica and try hands-on activities like grinding corn.

• American Revolution Museum at Yorktown – Featuring immersive galleries and an outdoor Continental Army encampment, this museum offers a fascinating glimpse into the daily lives of Revolutionary War soldiers.

For a break from history, we’d also like to spend a full day at one of the area’s amusement parks:

• Busch Gardens Williamsburg – Known for its thrilling rides, themed villages, and family-friendly shows.

• Water Country USA – Perfect for hot summer days with waterslides, a wave pool, and a lazy river.