This trip started because my 13-year-old mentioned that she wanted to visit Monticello.
As soon as she said it, I remembered my parents taking me there when I was a kid. I also remembered visiting James Monroe’s home, which was called Ash Lawn back then. I was not exactly trying to recreate that childhood trip, but it made me think Charlottesville would be a good place to take both of them.
We visit a lot of museums and historic places, so this felt like a natural little educational getaway. I could return to places I had not seen in decades, while mixing in enough other activities that the trip did not feel like one long history lesson.
It also became our first overnight getaway with just the three of us.
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How the Trip Came Together
I had already planned to take my vehicle in for some maintenance, so I decided to rent a car for the trip while mine was in the shop. I had reserved a minivan, but when I arrived, I was given the choice of waiting for one or taking a Kia Telluride at no additional cost. I took the Telluride.
It was roomy, drove nicely, and had captain’s seats and plenty of charging ports. Both of them liked it, and overall, I did too.
We loaded the car and left around 12:30, then almost immediately ran into traffic. Between the tunnel and bridge construction and the usual Hampton Roads congestion, we sat in traffic for about an hour. Once we finally made it through Hampton and Newport News, the rest of the drive was easy.
During the ride, I told them I had a surprise planned for later.
My daughter immediately wanted to know what it was.
“I don’t like surprises. Tell me.”
She kept asking, so I finally told her the surprise was that we were going out to eat.
“That’s the surprise?”
“Yep.”
Apparently, dinner was not a very impressive surprise, but it stopped the questions. 😂
We arrived in Charlottesville around 3:45 and checked into the Holiday Inn Express in the Pantops area. I did not want to stay downtown. I wanted easy parking and a location that would make it simple to get to Monticello, restaurants, and the other places on our itinerary.
Check-in was quick and easy. I had requested a high floor, and we ended up on the fifth floor, which was the top floor. Our room had a nice view of the mountains in the distance. The room itself was decent, with some normal wear and tear, although I did have to return to the front desk for extra towels and bedding for the pullout couch.
Breakfast was good both mornings and had plenty of options. The pool area was also a nice surprise. The pool was warm, the hot tub was actually hot, and everything worked. We even had the whole area to ourselves when we used it.
After checking in, we rested in the room for a little while. My daughter and I also looked through the brochure rack in the lobby, which is something we always enjoy doing when we travel. Sometimes we find another place we might want to explore or something we did not know was nearby.
One of the brochures was for Unlocked History Escape Rooms. We picked it up and said something like, “Oh, an escape room,” but neither of them had much of a reaction. Nobody said they wanted to go, so I put the brochure back and acted like nothing was going on.
Meanwhile, I knew exactly where we were going.
A little later, I told them it was time to leave for “dinner.” I missed the turn and had to circle back, but when I finally pulled up in front of the building, my daughter recognized it from the brochure.
“Oh, this is that place we just saw.”
They were still waiting for me to explain where the restaurant was.
“We’re not going to a restaurant,” I told them. “We’re going here.”
“We’re going to the escape room?”
“Yes!”
It was the first escape room for all three of us. We did The British Are Coming, and our mission was to find the Declaration of Independence, which had been hidden somewhere inside Thomas Jefferson’s home at Monticello.
The theme fit our trip perfectly because we were touring the real Monticello the following morning.
Inside the room, we had to solve codes, open locks, use coordinates on maps, and connect different clues. My daughter rang the help bell once, and the host also checked on us and gave us a couple of small hints when we needed them.
We found the Declaration of Independence and finished with about three minutes to spare.
They both said it was so much fun, and it ended up being one of the biggest highlights of the trip.
After the escape room, we went to Riverside Lunch for dinner. Riverside has been serving Charlottesville since 1935 and is known locally for its flat-pressed burgers and classic diner atmosphere.
It was exactly the type of local restaurant I enjoy finding on a trip. You walk in, sit wherever you want, and someone comes over to take your order. The menu includes more than burgers, but we were there for the thin, flat-top hamburgers.
The burgers came plain, and you could add toppings for a small extra charge. We also ordered a basket of crispy fries and breaded jalapeño-cheddar cheese balls, which were really good.
The food was simple, casual, and exactly what I hoped it would be. Riverside did not feel like a restaurant trying to reinvent a hamburger. It felt like a longtime neighborhood spot that already knew what it did well.
We made it back to the hotel just as it started raining, and storms continued off and on for the rest of the evening.
Monday at Monticello
We had a 9:15 a.m. Highlights Tour reserved at Monticello on Monday morning. The Highlights Tour is one of Monticello’s official house-tour options.
I had an America 250 Virginia pass booklet that qualified us for 15 percent off admission after collecting more than one stamp. I had already purchased our tickets online, but Monticello refunded the discount when we arrived. I was also able to use the same discount at Highland the following day.
Our guide was Steven, and he was excellent. He was very knowledgeable but explained everything in a way that stayed interesting and easy to understand.
The house was filled with unusual features and details. My daughter especially liked the parlor doors that moved together when one side was opened, while my son liked the underground passage beneath the house.
I was impressed by Jefferson’s enormous range of interests. The house included books, maps, fossils, taxidermy, marble busts, inventions, and all kinds of reminders of how curious he was about the world.
One of the best parts for us was recognizing rooms and details that had inspired the escape room the night before.
As we walked through Monticello, I kept saying, “See? This is the room we were in last night.”
They would look around and say, “Oh yeah, it is!”
That little connection made both activities more memorable. The escape room gave them details to recognize, and seeing the real house made the escape-room story come to life.
After the tour, we walked through the gardens and grounds, visited Jefferson’s gravesite, explored the museum, and looked around the gift shop. The gardens were beautiful, especially the sunflowers, and the property had some amazing views.
I also added another magnet to my collection, off course.
We had lunch at the Monticello café before leaving. My son ordered a children’s turkey sandwich, although he was disappointed because the center was extremely cold. My daughter and I ordered turkey-and-Brie sandwiches with soup. The sandwiches came on warm baguettes with melted Brie and were delicious.
I chose the tomato soup, while she ordered the chicken-and-sausage soup. Hers was thick and full of vegetables.
After lunch, we went back to the hotel and relaxed before heading down to the pool. The warm water and hot tub felt perfect after spending the morning walking around Monticello.
That evening, we ate at Tip Top Restaurant. I had breakfast for dinner, my son ordered spaghetti, and my daughter had dolmades and soup. Before leaving, we chose three large slices of cake to take back to the hotel: New York cheesecake, chocolate cake, and tiramisu cake.
We ate our desserts in the room while watching a marathon of The Office, including my favorite episode, “Stress Relief.”
Sitting in the hotel eating cake and laughing together was not a major part of the itinerary, but it became one of my favorite memories from the trip.
Tuesday Before Heading Home
On Tuesday morning, we ate breakfast, packed the car, and checked out. Our first stop was Carter Mountain Orchard.
We had visited once before when my daughter was younger, and somehow my husband had pulled our travel trailer up the mountain with my Pathfinder. Driving up again in the Telluride made me wonder how we had ever managed it.
The climb has some steep sections, but the views over Charlottesville were worth it.
They were not offering peach picking that day, so we walked around the market instead. We purchased nectarines, packaged apple cider donuts, and a large glass jug with a lid for only $2.
I plan to fill the jug with shells and sea glass, which has absolutely nothing to do with an orchard, but that is what it is becoming.
From Carter Mountain, we drove to James Monroe’s Highland. Highland was one of Monroe’s residences from 1799 to 1826 and is now owned by William & Mary.
Highland had a simpler and more rustic atmosphere than Monticello. The interior did not impress me as much. There was quite a bit of decorative interpretation, and I do not remember seeing many belongings that were directly connected to James Monroe.
The grounds and animals were the stronger part of the visit for us.
Highland had two donkeys, four sheep, chickens, and a working apiary. We were able to pet the donkeys and two of the sheep, which my son named Willie and Cornflake.
When we started walking away, the sheep began baaing after us.
They also completed a small scavenger hunt and chose prizes afterward. I love when historic sites include activities like that because it gives younger visitors something specific to look for while they explore.
Highland’s working apiary offered a one-pound jar of honey with a $25 donation, so we made the donation and brought a jar home.
We finished at Highland earlier than expected and decided to head home. Once we reached the Petersburg area, I left the interstate and took Route 460. I did not want to deal with the tunnel construction again, and I was tired of the fast-paced interstate driving.
We stopped at the Virginia Diner for lunch. My daughter was excited because Guy Fieri had visited. She ordered pulled pork, I had a fried-chicken sandwich, and my son chose a cheeseburger.
Shortly after we returned to the road, it began pouring. We drove through alternating patches of light rain and heavy downpours for much of the final hour.
Route 460 was calmer traffic-wise, but the weather made the drive stressful. We made it home safely, unloaded later when the rain eased, and returned the rental car.
That was a wrap on our first overnight getaway with just the three of us.
Is Two Nights in Charlottesville Enough?
Two nights worked really well for this trip.
We had enough time to tour Monticello, visit Highland, stop at Carter Mountain Orchard, try an escape room, eat at local restaurants, swim at the hotel, and still have time to relax.
Monticello was the biggest historical highlight. The escape room was the unexpected favorite, especially because its theme connected so well with our Monticello tour. The animals were the best part of Highland, and eating cake while watching The Office became one of my favorite memories.
The trip was educational without feeling like school. We learned some history, solved puzzles, enjoyed mountain views, ate good food, met friendly animals, and spent time together.
For a short family getaway, that was exactly the balance I wanted.
Find More Things to Do in Charlottesville
We chose Monticello, James Monroe’s Highland, Carter Mountain Orchard, and an escape room, but there are plenty of other tours and activities in the Charlottesville area.
Browse Charlottesville tours and activities on Viator
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