In the summer of 2019, I went on an extended 15-day East Coast road trip with my two kids. With so many East Coast road trips I looked at online, they were only one way! Like, how did you get back home? To me, a road trip involves leaving your home in your car, and rolling back into your driveway in your car sometime later. Here, I’m talking about a East Coast US History road trip from our home in New Hampshire down to North Carolina, and then back home (because we were already at 15 days at that point, and how long can you sustain that for?)
I would have loved to have gone all the way down the east coast to Florida, but then we’d have to drive all the way back up and it becomes super long and expensive at that point. As a wedding photographer, I don’t have that much time off during the summer. For this trip, I had two Saturdays in a row that I did not have a wedding booked, so I snatched that opportunity to plan a trip with my family in between those dates.
New Hampshire to North Carolina
Sleepy Hollow | Washington DC | Williamsburg | NC | Monticello | UVa | Gettysburg | Philadelphia | New York
Day 1: Sleepy Hollow and New Jersey
We took off on our first day of driving. Dave was with us in the beginning, so he did the driving which was wonderful because I was on my own after the 4th day. We were heading towards Washington DC but it’s a really long drive from New Hampshire, so I planned an overnight stop in Edison, New Jersey to break it up a little. I absolutely hate driving more than about 3-4 hours per day. Also, to avoid us having to drive directly through New York City, I scheduled a little detour to Sleepy Hollow, NY. This actually ended up being one of my favorite little discoveries of the whole trip.
Walking through this little hamlet, it is not a big stretch of the imagination to be transported back to the tale of the Headless Horseman. I actually had no idea the Old Dutch Church or the bridge were real, but they are and were!
Back on the road, we got turned around in a few places and went over bridges I hadn’t meant for us to go over. In fact we needlessly went over all of Staten Island, somehow, at great expense of like a $15 toll. Oh well. We finally made it to New Jersey and landed at the Home2Suites in Edison. They had a nice gym that Parker enjoyed.
Days 2-4: Alexandria, VA and Washington DC
We escaped from NJ and made it to our first “real” destination: Alexandria VA. Dave’s brother lives in Alexandria and as a result Dave and the kids have been down to visit him many times! For me, this was the first time I had been to DC in almost 20 years. We stayed at the trusty SpringHill Suites on Eisenhower Ave near Old Town which is where Dave and the kids always stay when they go to visit because it’s very close to Doug’s place. We were there for 3 nights, and Dave’s brother was a wonderful tour guide for all things DC and Alexandria.
The Mall, Museums, and Monuments
The first day, we explored all the fun things on the Mall. We hit the Metro and made our way into the city.
Our first stop was the National Archives where we saw the Declaration of Independence, the Constitution, and the Bill of Rights. Then, Dave, Doug, and the kids went to the Air and Space Museum while I went to the National Museum of the American Indian, which I loved. I loved how the landscaping included plantings of native crops and flowers, as well as moving water features, totems, and the four cardinal directions. There was so much to look at and appreciate around the outside before I ever even went into the building. I was mesmerized and could have spent hours there, but we needed to meet back up as a group and keep going.
It was super hot that day, as it often is in late July, so we dragged ourselves all over the mall. Ice cream was in order. The Washington Monument was closed, but the Lincoln Memorial was open. I know the kids had been there before, but I wished they could fully appreciate the magnitude of that memorial. The Lincoln Memorial is magnificent and I was verklempt as always by the succinct and solemn eloquence of the Gettysburg Address which I memorized a few years ago. Excited to finally be going to Gettysburg in a few days!
After passing by the WW2 and Korean War memorials, we walked all the way around the basin to get to the Jefferson Memorial, in the sweltering heat. And guess what? It was closed for renovations to the dome. Two of the major monuments were closed at the same time, which was super annoying. I was bummed because I really wanted this Jefferson lesson to tie into our visit to Monticello later in the trip.
Alexandria Old Town and Farmer’s Market
One morning we spent exploring some of the sights in Old Town, including the amazing farmer’s market. We all really enjoyed the samples of peaches which were beyond delicious.
The scenery in Old Town Alexandria is simply beautiful, with all the historic homes and buildings. It’s a very vibrant community with plenty of pedestrians, public transportation, coffee shops, restaurants, and parks.
One night we went out to eat at a Mexican restaurant called Tacos and Tequila. The food was great and the margarita was refreshing! After all that sweating I had done walking around DC, I was happy for that salted rim.
Finally, after three nights, it was time to say goodbye to DC and continue on our way. It was also time to say bye to Dave, as he couldn’t spend the full two weeks on the road with us. He flew back on a quick flight to Manchester, while the kids and I hit the road towards Williamsburg.
Day 5: Williamsburg VA
After a few hours of driving, we arrived at our hotel for the night: the Embassy Suites in Williamsburg. This hotel had an amazing cooked to order buffet breakfast, as well as wallpaper that looked like historic maps and scenes.
After we checked in, we didn’t stay long because we ran out again for an early supper at the nearby Red, Hot, and Blue barbecue place (which is now permanently closed). All of us love bbq so it was an easy choice. Drew’s favorite food is ribs.
The next morning we had a wonderful hot breakfast at the hotel, packed our stuff, and went over to Colonial Williamsburg. It was a good thing that we went early because it got hot quickly and we melted, gasping. Strangely, there were not a lot of people around and it wasn’t at all like I remembered it from when I went as a kid. It was not my favorite place that we visited on this trip. Still, we needed a midpoint between DC and NC.
Eventually we got tired of walking in the crazy heat, so we made our way back to our car in the 21st century and started a very tough 4 hour drive to North Carolina to my parents’ house. We traveled some very remote state highways with remnant signs for old plantations all along the way. We also got caught up in the most intense and violent rain and thunderstorm that scared the mess out of Parker. We had to pull over on the side of the road under a bridge and wait for it to let up because I literally could not see out the windshield. Parker still talks about that storm to this day.
Days 6 and 7: North Carolina
When we finally got to my parents’ house, we had reached the southernmost point of our trip and we were happy to be out of the car! So glad to be home where we can rest, visit Mom and Dad, do some much needed laundry, clean out the car and listen to the sizzle bugs while rocking on the front porch. Happy to hang out there for a couple of nights and recuperate. My old clunker of a car was holding up just fine so far, which was my biggest worry.
I would have liked to keep going but the trip was already massive and we weren’t even halfway and I had weddings to get to. Enjoyed dinner with my brother and sister in law, with awesome leftovers for breakfast before we hit the road in the morning! Loved the locally made peach 
ice cream from Homeland Creamery– a summertime favorite. Also happy to be able to see the pretty southern flowers blooming like the crepe myrtle which I have missed, and I enjoyed seeing the four-o-clocks opening the past couple of evenings.
Day 8: Monticello and Charlottesville, VA
Our goal for this day was to arrive at Monticello for our 3:00 kids tour, and I’m not bragging but I timed the entire day so that we arrived exactly when we were supposed to. Our day started out driving north and eventually we hit downtown Lynchburg to grab some lunch. I had found a place on Trip Advisor that I thought would be fun, and it was wonderful! Market at Main has a huge menu, and a quaint interior.
We rolled into Monticello for our 3:00 kids’ tour which was very detailed and involved. The guide had us sit on the floor in each of the rooms and explained the architecture, influences, and historical relevance to Thomas Jefferson’s life at Monticello. We were the only ones, so it was a 40 minute private tour that kept the kids heavily engaged. I’m still bummed that the Jefferson Memorial was closed in DC because that would have been a great tie-in. For the rest of the day, we explored on our own. Since it was later in the afternoon, the crowds had gone so it was pretty quiet by the time we left.
We headed towards our hotel and stopped at Mission BBQ which was just around the corner. Great place! I had never heard of it, but it’s a chain. We can never have enough barbecue. And Parker lost a tooth there!
In Charlottesville we stayed at the Hyatt Place at which I used points to take care of 50% of the cost. Great deal! This hotel had a pool which the kids loved, and it also had an amazing breakfast.
Day 9: UVa and Gettysburg
The morning that we woke up in Charlottesville was an unusual one because I found myself with a rare empty morning. All we had to do was get to Gettysburg by the evening. I decided that we’d go over to the University of Virginia and see the Rotunda and the historic part that Thomas Jefferson designed. This, along with Monticello, is a UNESCO world heritage site. On the top floor of the Rotunda, there is a little museum where we learned about the great fire that destroyed the whole thing in 1895.
The university was completely empty since classes had not started yet, and we enjoyed wandering around. We even found Edgar Allen Poe’s old room which fascinated me. I did not know he had a connection to UVa, so I was pleased at that serendipitous discovery.
We hit up a snack at Duck Donuts before hitting the road. We’d been to one of these in NC, but a donut is always welcomed!
We enjoyed an easy but long drive up to Gettysburg, and I’m pretty sure it was the first time I’d ever been to Pennsylvania.
I am in love with this peaceful small town with a big place in history. Cornfields come right up to the commercial areas and the people are friendly. This was the most important stop for me on this trip and I feel our time here is too rushed (will have to come back *without kids*). We went to the historic town center which is adorable.
Our hotel was the Hilton Garden Inn on York Road. We kept it simple that day, and grabbed Arby’s next door, and snacks at the grocery store right behind the hotel. A little pool swimming finished off this relaxing day.
Day 10: Gettysburg Battlefield, Pretzels, & Philadelphia
First half of the day in Gettysburg was incredible. After watching the Ken Burns Civil War documentary a number of times over the years, I’ve always wanted to go to Gettysburg and today that came true. We did the whole experience: the film, cyclorama, museum, and TWO HOUR bus tour of the battlefield. The kids did great and I know it wasn’t easy for them to endure or even understand any of it. It’s pretty heavy stuff. I just hope that when they study it in school maybe it will ring a bell somewhere in their lizard brains.
Immediately after the long morning at the battlefield, I needed to lighten the mood for these guys so we did a lunch at McDonald’s which provided a view of the entrance to Soldier’s National Cemetery, just up the hill. This is where Lincoln gave the Gettysburg address, and unfortunately we didn’t make it over there on this trip. I think this just leaves the door open for another visit!
Then, for levity, we went to the Utz Snacks factory to see how they make potato chips! And also went to the Snyder’s of Hanover Factory Store. Drew was in heaven because he’s my pretzel boi. 
At Utz they provide a self guided tour to see the factory, and they give you a little bag of chips on the way out. It was amazing to see the whole process from a viewing platform over the factory floor, from potato to finished product in the bag.
At Snyder’s (just a short drive away) there is no tour, but you can shop in their factory outlet which was amazing to see all the varieties that you can’t always find at your own grocery store. Great prices! We got a huge bag of stuff for $9, and one thing you definitely need on a road trip is snacks.
Then, we hit the road to Philadelphia and that is where the day was ruined because what was supposed to take 2.5 hours was actually 5 hours. I was super annoyed. We parked in the garage at Reading Terminal Market, and I used a super smart Spot Hero pass to save 50% on that. We just chilled in our swanky hotel that night which I scored with a Hotwire secret hot rate (it’s supposed to be a blind booking but you can totally figure out which one you’re getting–google it). We were there for two nights on the 17th floor (no view, but they don’t give views to the Hotwire customers). We stayed in the Loews Philadelphia Hotel in the heart of City Center, and it was the first skyscraper in the US. And Parker lost another tooth that night!
Day 11: Philadelphia Old City
I was pleasantly surprised by the history in the Old City of PHL. I knew there was a lot, but there is so much more than I ever realized, and it’s all so compact and walkable. We took a guided walking tour in the morning through the National Constitution Center. That tour covered some incredible places, and it was short enough at 75 minutes that the kids could handle it. I was able to get the tickets for that tour for free using my points! Then we went back to many of those places afterwards to spend a little more time in each.
We saw Independence Hall, another UNESCO world heritage site, the Betsy Ross house 
and the Liberty Bell 
, Ben Franklin’s grave and the site of his house and print shop.
There was a small light bulb moment 
when in Independence Hall, the ranger explained that the original Declaration of Independence is in Washington DC at the US National Archives and Drew goes “we saw it!” And so my work is done. All I’m hoping for is a small flicker of recognition or connection between the things and places that we’re seeing.
Lunch: There is one great cheesesteak shop in the Old City: Sonny’s Famous Steaks. This one was super easy for us to get to, and so that’s where we went for lunch. I kinda entertained the idea of taking them to Geno’s and Pat’s which are right across the street from each other, but they are not in the neighborhood at all so I couldn’t be bothered to figure out transportation down to South Philly. Sonny’s was fine for us, and we enjoyed it although we found it wasn’t that different from the shaved steak or cheesesteak that we get in New England.
Right next door to Sonny’s is a dessert café called Happily Ever After that has cereal puffs in liquid nitrogen called Dragon’s Breath. We had to sign a waiver to eat it! It was fun although we were all terrified at the time.
Day 12: New York
Wrapped up Philadelphia in the morning with a quick walk through Love Park and then hit the road to New York, the final stop in our East Coast road trip. We’re just getting our bearings but we had amazing pizza and took a ride on the Roosevelt Island tram 
. Then hit up Dylan’s Candy Bar. The troops’ morale is low, they’re all homesick. They can’t keep up with this rolling stone. 
We stayed at the Fairfield Inn Midtown Manhattan, just a block down from Madison Square Garden and overlooking Penn Station. It was a great location for everything we wanted to do, and close to all the trains.
Day 13: New York
Took the ferry from lower Manhattan over to DUMBO and explored for a bit before walking back over the Brooklyn Bridge. So neat! Had lunch at the same pizza place as yesterday, so good. Got some banana pudding from Magnolia Bakery, and it’s legit (although not exactly hard to make or screw up). Grandma Faye would approve 
Then I wanted to introduce the kids to my personal favorite thing to do on trips which is a food tour! We did a sweets/dessert tour in the Chelsea/High Line/West Village areas and had a great time. Finally made a last stop at Seinfeld’s diner because I couldn’t not do that.
Day 14: New York
Had a long and interesting day on what I like to call a “lazyman” tour where you get carted around on a little bus at breakneck speed to see like 4 days’ worth of highlights in 6 hours. The day was jam packed but sooooo nice to be driven around. This tour was run by USA Guided Tours NY and I booked it on Chase travel using all points. This would have been a $247 cost if I’d paid cash! The 9/11 memorial is very moving. Finally got an enthusiastic reaction out of Parker–he was so impressed with the Statue of Liberty on the boat portion of the tour. We also found the NBA store which he loved 
. I tried to get to the NY Public Library before it closed but failed, but still saw those staircases with the lions that creeps me out to this day. And went back to see our frens at NY Pizza Suprema yet again bc it’s just awesome.
Day 15: New York & Pez
Took a short walk from our hotel to the brand new billion dollar+ Hudson Yards mall where the newly-famous “vessel” is, which looks like a beehive to me. It’s free to go up, but you have to have timed tickets. Sooooooo dizzying. Headed home, stopped at the Pez Visitor Center in CT which was a bit of a museum dedicated to vintage and contemporary Pez dispensers. We ate lunch in a seafood shack in West Haven CT, and we were definitely feeling back on New England turf. Home at 6pm!
Note that we did not visit Boston because we have already been there so many times, and it’s easy to get to any time we like. If you were looking to do a similar American History road trip, then Boston would absolutely be a place you cannot miss. Like the Old City of Philadelphia, the historic part of Boston is compact and easily walkable (see the Freedom Trail).
Check out our 2018 road trip through Upstate New York!
