My parents were scheduled to go on a week-long Virgnia roadtrip, to culminate at the FSU vs. UVA football game in Charlottesville, VA at the end of the week. My mom ended up not being able to go on the trip, so I stepped up to go with my dad!
I haven’t spent much time in Virginia, I was in need of a break from work, and of course I was excited to spend some quality time with my dad on a historic Virginia roadtrip!
Day 1 – Lexington, VA
Day 2 – Lexington, VA and Appomattox, VA
Day 3 – Colonial Williamsburg
Day 4 – Jamestown, VA and Charles City, VA
Day 5 – Yorktown, VA
Day 6 – Williamsburg, VA
Day 7 – Charlottesville, VA
You can scroll through the full details below!
Historic Virginia Roadtrip Day 1 – Travel
We started our trip in Tallahassee, FL (we went to the FSU vs. ULM football game on Saturday) and got on the road on Sunday before the sun was up. We drove over 11 hours to Lexington, VA for our first night in Virginia. After checking into a hotel and asking the front desk where the best local place to eat was, we ended up at The Palms restaurant in downtown Lexington.
Check out my review of The Palms restaurant.
After a long travel day from Florida to Virginia, dinner was the highlight of the day.
Historic Virginia Roadtrip Day 2 – Lexington and Appomattox, VA
Not knowing what to expect, a visit to Lexington, VA and Appomattox, VA was recommended to me for some of the best Civil War history in Virginia. It did not disappoint!
A drive through the very unique-looking campus of the Virginia Military Institute, to Washington and Lee University where the Lee Chapel and Museum was our first historic stop.

The Washington and Lee University is a beautiful campus, and right in the center is the Lee Chapel and Museum where you can learn all about the history of General Robert E. Lee, his connection to George Washington and the University. There was a free tour guide in the chapel (donations accepted) that told us about the history of the chapel and the statue of Lee that was also in the chapel.

Downstairs, the office of Lee was closed off after his death. You can now view it exactly how he left it, like stepping back in time. The chapel building also includes a museum, gift shop, and crypt where Lee’s relatives are buried, including his horse Traveller right outside the door. We spent about an hour at the Lee Chapel and Museum.

After that we walked around downtown Lexington (right next to the University) and over to the Stonewall Jackson House, which is also very close to the Virginia Military Institute. The house that General Stonewall Jackson owned and lived in for a short time before joining the war was restored to look just like it did when he lived there. The paid tour will take you room by room to get a sense of the man Jackson was and how he lived.

After spending about an hour at the Stonewall Jackson house, we left the quaint town of Lexington, VA and drove an hour and a half to Appomattox, VA.
The Appomattox Courthouse National Historic Park is where you can view the homes and businesses that existed when the Civil War ended in their little village.

The McLean house, known as the “Surrender House” is within the Appomattox Court House village and is open to go in. This is the site where Confederate General Lee signed the surrender to Union General Grant. Could you imagine living in that house and witnessing the end of the Civil War right in your living room (or parlor rooms as they called it then)?

It was really cool to go into the home and see where history took place.
While at the park, we listened to a period talk presented by the tavern owner in the village. He was in full 1865 character and did a fantastic job giving you a good picture of what it would be like to be a part of this historical day.
We spent about 2 hours at the Appomattox Historical Park and then drove into the tiny downtown Appomattox for lunch before heading out of town.

Check out my review of Granny B’s restaurant.
The drive from Appomattox to Williamsburg, VA took about 2.5 hours, plus a stop in Petersburg, VA to tour the Petersburg battlefield. Civil War fighting lasted over 9 months in this area. You could easily spend a whole day here, but we only spent about an hour driving through the Eastern and Western front unit tour.
We finally arrived in Williamsburg at about 6:00 pm, in time to check into our place for the rest of the week, The Colonies at Williamsburg, and head on over to our dinner reservations at a Tavern house in Colonial Williamsburg called King’s Arms. We were told to check out one of the taverns to get a Colonial American experience.

The tavern is set up to look like a tavern from the 1700’s. The only lighting is candlelight at your table and the servers are dressed in colonial clothing. The menu also features a few items that were likely to be served during that time. I got the pork chops and they were very good. My only complaint is that the food took a really long time and since we were tired from our full day, we were getting impatient.
Check out my full review of King’s Arms Tavern.
Historic Virginia Roadtrip Day 3 – Colonial Williamsburg
Colonial Williamsburg is an area of Williamsburg, VA where you can walk (or bike) around the historic area of where the original settlement in Williamsburg was, check out the original Capital building and the Governor’s Palace, among other historical landmarks. We decided to rent bikes at a local shop right down the street called Bike The Burg. This was a great way to see Colonial Williamsburg!

Before heading over to the Colonial area, we first biked through a scenic route down S. England street, known only by the locals as a great biking or walking area away from town. The owner at Bike The Burg was nice enough to give us this fantastic biking recommendation.

After spending some time biking through nature, we turned around and headed back to Colonial Williamsburg. We biked through the college of William & Mary, which is right next to Merchant’s Square and the main Colonial Williamsburg area. The college is beautiful, all brick and very clean. We then biked over to Merchant’s Square which includes a bunch of shops and restaurants. We parked our bikes and ate a sandwich at The Cheese Shop and then walked around some of the shops.

Check out my review of The Cheese Shop.
My dad’s favorite in Merchant’s Square was The Peanut Shop. Every flavor peanut you could imagine! We went back a couple times during our trip.

After biking around Colonial Williamsburg and checking out some of the historical buildings, we biked back to the bike shop and turned in our bikes.
A nap back at the condo was welcome after a full day biking. After that, we went to dinner at another recommended place in Williamsburg: Food For Thought, and then caught a movie, Peanut Butter Falcon (I recommend!) before calling it an historic day!

Check out my review of Food For Thought.
Historic Virginia Roadtrip Day 4 – Jamestown, VA and Charles City, VA
Day 4 of our historic Virginia roadtrip started off with a drive on the very pretty and peaceful Colonial Parkway to Historic Jamestowne. We saw a baby fawn standing in the brush off the road. So cute!
Historic Jamestowne is a National Park area (be sure to bring your NP pass) and was the first British settlement in North America in 1607. You can walk around the grounds and museum where archaeologists have dug up remnants of buildings and artifacts from that time and get a feel for what it was like to be a Jamestown settler. Sounds like they had a rough time learning how to survive here.

There was an archaeological dig in progress in one area that we walked over to and watched for a bit. The lead archaeologist was nice enough to come over and chat with us a bit about what they found and are hoping to find in the area.
We also stopped at the Jamestown Glasshouse for a cool demonstration of the glassblowing. It was interesting to compare the differences and similarities to the glassblowing I toured on my recent Italy trip.
You can also drive over to the Jamestowne settlement museum, which is nearby Historic Jamestowne for an additional fee. We decided to pass on this and headed out of Jamestown along route 5 to Charles City, VA. We were told there were plantations to tour along route 5 and decided to check them out!
We first stopped at the Culs Courthouse Grill in Charles City, VA for lunch. This is a popular place for bikers to stop along their route 5 ride that goes all the way from Williamsburg, VA to Richmond, VA. The homemade bread by Viv is a must-try!

Check out my full review of Culs Courthouse Grill.
After lunch, we continued along route 5 to the Shirley Plantation. This is a beautiful working plantation that you can tour (house and ground for $25 fee). Our timing wasn’t right for the house tour (family members actually still live in the house), but we did the self-guided grounds tour ($11.00 fee) and enjoyed that. The house sits right on the James River and is beautiful.

That evening we went to Blue Talon Bistro with some local friends for dinner in Merchant’s Square.
Check out my review of Blue Talon Bistro.
Historic Virginia Roadtrip Day 5 – Yorktown, VA
Another pretty drive east this time on the Colonial Parkway to Yorktown Battlefield. By this point in the trip, I was feeling really smart and proud of my American history knowledge learned on this trip. I’m not sure I would have appreciated the trip as a kid or teenager, but found it very interesting as an adult.
Yorktown Battlefield is part of the Colonial National Historic Park (same as historic Jamestowne is, so if you bought tickets at either one, you can use it at the other within 7 days) and your admission is free with a National Park Pass. Yorktown was the last major battle of the Revolutionary War where General George Washington with allied American and French troops overtook General Cornwallis’ British army in 1781. The Park is a driving tour of the different battlefields and landmarks.

Along the tour you can stop at the Moore House where General Cornwallis signed the surrender and essentially ensured American independence.

Even cooler than the battelfield tour was stopping in downtown Yorktown area where you could tour the Nelson House, home to Thomas Nelson, Jr, one of the signers of the Declaration on Independence. You can still see the cannon balls stuck in the outside walls of the house from when when the British were occupying Yorktown and the American and French armies were taking it back in that final battle of the war.

We walked around the Riverwalk in Yorktown, a cute area with several shops and restaurants. We ate lunchat the Riverwalk Restaurant before heading back to Williamsburg where we took the afternoon to relax.
Check out my review of Riverwalk Restaurant.
Other things to do in Yorktown:
- York River State Park
- American Revolution Museum at Yorktown
Historic Virginia Roadtrip Day 6 – Williamsburg, VA
Our final day in Williamsburg, my mom flew up to join us for the weekend. We took her around some of our favorite spots in Williamsburg, including some new things we were saving. We started breakfast off at the Astronomical Pancake House. Williamsburg is loaded with pancake houses. I’m not sure why but we couldn’t leave without giving at least 1 a try. I picked this one because I like the name, and it had a pancake on its menu called the “chocolate insanity pancake”!

Check out my review of the Astronomical Pancake House.
After breakfast we went to the Yankee Candle store down the street. This is the biggest Yankee Candle store I’ve ever seen. It is more like a mall and toy store in one. They have toys, clothes, kitchen supplies, a popcorn and ice cream stand, Christmas shop, and of course candles.
After we loaded up on some candles, we headed out to the Williamsburg Winery for a wine tour, tasting, and lunch with friends that have moved to the area.

Next stop was a walk around Colonial Williamsburg to show mom, another stop at The Peanut Shop in Merchant’s Square, a drive along the Colonial Parkway and then back on route 5 to the Sherwood Forest plantation. We did another self-guided tour of this plantation. It was very different than the Shirley Plantation. Sherwood Forest was the home to President John Tyler, and his family still lives there. It felt kind of weird walking around someone’s house, but I guess they are probably used to it.

After a fun and long day of checking everything off our Williamsburg, Virginia list of things to do, we had 1 more dinner at Food For Thought. This was the only place we ate at twice, we really enjoyed it.
Historic Virginia Roadtrip Day 7 – Charlottesville, VA
Our last day in Virginia we traveled to Charlottesville for the Florida State versus University of Virginia football game. We didn’t spend any time in the town of Charlottesville itself, but walked around some of the campus, tailgated, and headed to the stadium. The game was a lot of fun, but we lost, not the greatest end to our historic Virginia roadtrip.

I admit that I didn’t know much about Civil War or American Revolution history before this trip. I never enjoyed history classes in school, but being able to visit these historic places and learn more about the individuals involved gave me a greater appreciation for the early years of our country.
I was also thankful for some fun quality time with my dad. My biggest recommendation from this whole trip isn’t a historic landmark or a favorite restaurant. It is to go on a trip somewhere, anywhere with your parent. The quality time away with them without your spouse, children, or siblings is priceless. I will always be grateful for this trip with my dad and hope we can do another one sometime!
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