Colonial Williamsburg with Kids and Grandma: History, Ghost Tours, and Tavern Dining
Colonial Williamsburg was our next stop on our summer 2025 road trip from Florida to Pennsylvania. After traveling through Georgia, South Carolina, and North Carolina, we continued north into Virginia for a destination that combines history, historic accommodations, family activities, and some fun experiences beyond the usual sightseeing.
We stayed at the Bracken Executive House, spent time exploring Colonial Williamsburg, enjoyed dinner at Shields Tavern, and took a ghost tour that turned out to be one of our favorite experiences of the trip.
Staying at the Bracken Executive House
We stayed at the Bracken Executive House, one of the colonial-style accommodations associated with Colonial Williamsburg. Staying in one of the houses on the property comes with access to the hotel’s pool and other amenities, which is a nice bonus, especially when traveling with a kid.
Our son took advantage of the pool during our stay, giving him a little break from all the history.
There was, however, one important detail I wish I’d paid more attention to before booking: the bedrooms and bathroom were upstairs.
My mom, aka Grandma, has mobility issues and would much rather avoid stairs. She managed them during our stay, but it was definitely a challenge.
I do my best to find unique places to stay because I love accommodations that add something special to a trip. Unfortunately, those character-filled properties aren’t always the easiest to navigate.
If you’re traveling with someone who has mobility limitations, I’d recommend asking specifically about the layout of the accommodation before booking. Photos don’t always make the number of stairs or the location of the bedrooms obvious.
Exploring Colonial Williamsburg
Most of our time was focused on exploring Colonial Williamsburg and experiencing the historic area.
There’s something special about spending time somewhere that feels so different from everyday life. Rather than simply visiting a museum, you’re walking through a historic setting and getting a sense of the architecture and atmosphere of an earlier time.
It’s also a destination that works well for a family trip because you can mix sightseeing with other activities. Our son got his pool time, while the adults enjoyed the history and atmosphere.
Dinner at Shields Tavern
No stay in Colonial Williamsburg is complete without a meal in one of its historic taverns!
We had dinner at Shields Tavern, where the peanut soup is a must-try. If you know, you know!
Eating in a historic tavern is part of the fun of visiting Williamsburg. After a day spent wandering through the historic area, sitting down for a meal in a setting that fits the destination really helps bring the experience together.
If you’re planning a visit, I’d recommend making a tavern meal part of your itinerary rather than treating it as an afterthought.
The Williamsburg ghost tour: A 10/10 experience
During our stay, we also took a Williamsburg ghost tour, and it was a 10/10!
The young woman leading our tour was a fantastic storyteller. She really knew how to breathe life into her spooky stories, making the experience much more engaging than simply listening to someone recite historical facts.
The tour ended up being a favorite for both our son and Grandma. That’s not always easy to accomplish when you’re traveling with different generations, so it was especially nice to find an activity that everyone enjoyed.
The walking was manageable enough for Grandma to keep up, and although there were some stairs, she was able to handle them.
For us, the combination of storytelling, history, and spooky tales made this one of the highlights of Williamsburg. If you’re visiting with kids or older family members, I’d definitely consider adding a ghost tour to your plans.
A little time outside the historic district
Just outside Colonial Williamsburg, there’s a small downtown-style area with restaurants, shops, and a wine bar.
My husband and I enjoyed the wine bar while our son and Grandma did some shopping. It was a nice opportunity for everyone to do something they enjoyed without needing to plan an elaborate activity.
I always appreciate destinations that offer a mix of experiences. Sometimes you want to spend the day immersed in history, and sometimes you just want to browse shops or relax with a drink.
Would we return to Colonial Williamsburg?
Absolutely!
Colonial Williamsburg is a beautiful area with plenty to do, and it’s definitely on our list of places to revisit. In fact, I should probably create a dedicated list of all the places we want to return to and keep it somewhere on this site!
Between the historic setting, the tavern dinner, the ghost tour, and the family-friendly amenities, there was enough to make our stay memorable.
My biggest takeaway is to pay closer attention to accommodation layouts when traveling with Grandma. The upstairs bedrooms and bathroom were manageable, but not ideal. The ghost tour, on the other hand, was a definite win.
If you’re planning a trip to Colonial Williamsburg, I’d allow enough time to explore the historic area, enjoy a meal at a tavern, and fit in a ghost tour. It’s a destination that offers more than just a quick walk through history.
Continue Following Our East Coast Road Trip
This stop was part of our summer 2025 road trip from Florida to Pennsylvania, where we explored seven states along the East Coast. Follow along with the rest of our journey for more historic sites, quirky roadside attractions, honest hotel reviews, and practical tips for traveling with family.
Read the full trip itinerary: Summer 2025: Our East Coast Road Trip from Florida to Pennsylvania
Explore more stops along the way:
- Georgia and South Carolina
- North Carolina’s Pickle Adventure
- Colonial Williamsburg, Virginia
- Crystal Grottoes Caverns and Antietam, Maryland
- Shepherdstown and the Bavarian Inn, West Virginia
- Flight 93, Punxsutawney Phil, and Erie, Pennsylvania