A Quick Escape

Williamsburg, Virginia

This past Labor Day weekend we took a fun family trip to Williamsburg, Virginia. Looking back, it turned out to be one of those surprisingly smooth vacations that we’ll remember fondly.

The Story Behind the Trip

Last year for our 10-year anniversary, my husband and I renewed our vows in Las Vegas. While we were there we sat through a timeshare presentation and “won” a free trip. Well, this was that trip. So our agenda was simple: leave early Friday morning and hit the road for roughly eight and a half hours.

Road Trip with Kids: What Worked

Traveling with the kids for that long could’ve been… daunting. But over the years, we’ve found some things that have made traveling easier:

• I didn’t plan it ahead of time this trip, but the kids thoroughly enjoyed looking through my magazines. Next time I’ll bring kid-friendly magazines specifically (instead of using my Food & Wine magazines)

• I try to keep coloring books and crayons readily available

• Sometimes, I give the boys magnatiles and Legos for in-car entertainment

  
  

I always try to put off the iPads as long as possible, but about half way through our trips, I end up giving them their iPad entertainment. Towards the end of this drive I started a Disney movie on my phone and propped it up so we could all watch together in the car. It truly wasn’t nearly as bad as I thought it would be.

First Evening in Colonial Williamsburg

We arrived a little before dinner and checked into our hotel (not fancy—but free thanks to Vegas—and totally fine for what it was). Then we made our way into Historic Colonial Williamsburg and simply walked the streets. It was so beautiful, and our kids absolutely loved exploring. I highly recommend going later in the day when fewer people are around. We did just that, then found a little restaurant nearby for dinner at DoG Street Pub. We all had fish & chips and they were spectacular.

Saturday: Breakfast & History

The next morning we got up and ate at Shorty’s Diner in Williamsburg. The food was very, very tasty and filled us up big time. We were going to try a pancake house (there are a ton of pancake houses in the area… Our eight-year-old told us that it’s because George Washington loved pancakes… Google it), but those were all super packed, so we switched to Shorty’s and were glad we did. After breakfast we headed to Jamestown Settlement. The indoor museum outdoor village experience was so much fun! The kids especially loved the Indian village and seeing how they made canoes, and later touring two different ships and imagining life on board. I was amazed at how much there was to see. 

After that, we drove through some of the battlegrounds on the way to Yorktown, Virginia, which turned out to be a highlight for me. In Yorktown, we wandered the shops and let the boys get their feet (and eventually whole bodies) in the water. The setup was just so charming in Yorktown

with local shops on one side of the street, the little beach on the other, no high-rises blocking the view, and the bridge right there beside us. It felt relaxed and unhurried, which is right up my alley. For lunch we stopped at Yorktown Pub. We shared seafood and nachos while watching the Georgia game. They had great food and a fun vibe! 

Sunday: A Scenic Drive & Onward Home

The next morning we headed for the Chesapeake Bay Bridge‑Tunnel, which made me nervous at first, but it turned out to be super cool. We had to explain to the boys that we were going underwater in the tunnel and coming out a little further along. Later, as we were driving across the bridge portion, we saw a huge container ship passing in front of us, and it finally clicked with them that the tunnel was going underwater. By that point, my four-year-old was holding his breath to pretend he was underwater too. They (and we) thought it was super cool traveling underwater like that. Hours later, we made our way home and by the time we pulled into the driveway we were beat, but we were grateful we had that Monday off for Labor Day. Long story short, don't sleep on the excitement of Williamsburg. We had a blast!