Here’s Our Top 10 Cities We Visited In 2019

In 2018 – the first year of our road trip – Shae and I stayed in more than 50 cities. That number dropped to 37 in 2019 as we realized we’d prefer to stay longer in fewer cities than move more frequently in order to stay in more places.

At the start of 2019 we put together a top 10 list of each of our favorite cities from the previous year, so I thought it’d be fun to look back and create a similar list of our top 10 cities from 2019.

I’ll say now – I found it incredibly hard putting these in order. My top 5 cities could easily be jumbled up in a completely different order and I don’t think I’d be able to argue with the results. Each of those cities had their own unique selling points, so my favorite could also vary depending on how I’m feeling that day.

Anyway, here are both of our top 10 favorite cities from 2019.

Stephen’s Top Picks

1) Waterbury / Stowe, Vermont

Waterbury and Stowe are right next to each other in central Vermont, so I figured I’d pair them together even though we actually only stayed in Waterbury.

Vermont has been one of my favorite states so far as it’s simply stunning. We visited Vermont in May/June of both 2018 and 2019, so it was perfect weather while we were there which certainly helped. There are mountains everywhere you look, while the Waterbury / Stowe area in particular has all kinds of excellent breweries, wineries and distilleries, as well as great places to eat like Ben & Jerry’s.

Neither of us are skiers, but it seems like this is also a great location for winter sports if that’s your sort of thing.

2) Roanoke, Virginia

Before setting off on the road trip, Shae and I lived in Portsmouth, VA for about 7 years. I really liked living there, but a couple of different Virginian cities have made my list.

The first of these is Roanoke which is in the western part of the state. It’s near the Appalachian Mountains, so there’s lots of good hiking including one of my favorite hikes – McAfee Knob. You can get a great view of the city up at the Mill Mountain Star, there are some good restaurants and breweries and the weather is far less humid in the summer than it is in Portsmouth.

We’ve visited Roanoke several times in the last few years and I’ve enjoyed it every time.

3) London, Kentucky

Kentucky was a huge surprise for me when we visited in April. I’d expected it to be fairly boring and backwards, but it’s been one of my top 3 states so far.

Having London be my favorite city in Kentucky was also a surprise as I’d not heard of it until we booked a hotel there. There was a Country Inn that was a bargain when using points and which seemed to be close to several activities people had recommended which is why we ended up staying in London.

As it turns out there’s lots to do, including hikes to Dog Slaughter Falls at Cumberland Falls State Resort Park and Tri-State Peak where you can view Kentucky, Virginia and Tennessee, the birthplace of Kentucky Fried Chicken, great restaurants such as The Wrigley Taproom & Eatery and Sonny’s BBQ and more.

4) Louisville, Kentucky

We didn’t know anything about Louisville before booking a week there, but we got lucky by booking a fantastic Airbnb in the NuLu district. NuLu was the perfect location as it had loads of great restaurants, bars and distilleries, while also being close enough to walk to downtown Louisville. We enjoyed Thunder Over Louisville – an excellent 30 minute firework display set to music – and returned a few weeks later to attend the 2019 Kentucky Derby.

5) Richmond, Virginia

Roanoke was my favorite city in Virginia, but Richmond wasn’t far behind. It’s on the James River and we love heading over to Belle Isle whenever we visit. There are so many great restaurants including Carytown Burgers & Fries, Bottoms Up Pizza and Buz & Ned’s BBQ.

One of the other great things about Richmond is that there are so many free things to do.

6) Washington D.C.

We’ve visited Washington D.C. a number of times before, but we also spent more than a week there in 2019. Similar to Richmond, Washington D.C. has tons of free things to do as there are so many museums, galleries, monuments, etc. that don’t cost anything to visit.

7) Davis, West Virginia

London surprised me as being my favorite city in Kentucky, while Davis surprised me as being my favorite city (well, town) in West Virginia. It has a population of fewer than 700 people, so it’s hardly a bustling metropolis. That’s part of its charm though as it’s a cute town with some decent bars and eateries.

It’s all the outdoor activities nearby that really make Davis shine. Dolly Sods Wilderness, Seneca Rocks, Blackwater Falls State Park, Spruce Knob, horseback riding and more – our 11 days there were unexpectedly fun.

8) Memphis, Tennessee

We stayed in four cities in Tennessee – Chattanooga, Memphis, Nashville and Knoxville. Three of those cities were OK, while there was one I liked far more than the others – Memphis.

There are some excellent Civil Rights places to visit like the National Civil Rights Museum (which is at the Lorraine Motel where Dr Martin Luther King Jr was assassinated) and the Slave Haven Underground Railroad Museum. There’s quirky stuff like the Peabody Ducks at the Peabody Memphis hotel and so much good food, especially BBQ.

9) Lexington, Kentucky

I enjoyed Kentucky so much that three of its cities made it into my top 10 of 2019, with Lexington being the third. We ended up spending 16 nights which was a few nights longer than originally expected as Shae organized a beer and canoeing trip for my birthday.

There was loads to do in the area, from canoeing to Claiborne Farm (where Secretariat is buried) to a race horse retirement farm to lots of great food to the Buffalo Trace Distillery to hiking and even more hiking (albeit 90 minutes away).

10) Newport, Rhode Island

Shae and I stayed in Providence during our time in Rhode Island, but visited Newport a few times as we really liked it there. The cliff walk had some beautiful views, there was a fun kite festival one day and spent an evening on the beach.

Shae’s Top Picks

1) Newport, Rhode Island

Originally, I had Montpelier VT as my top city, but then I realized we didn’t actually stay there in 2019. That moved Newport, RI to the top of the list. I loved that it was by the beach. The weather was nice, the people were friendly and there were great outdoor activities. I’d definitely like to see it in several seasons.

2) Portsmouth, Virginia (Hampton Roads)

This is “home”, so I’m not sure it’s fair to compare it to other places because we know all the best spots to go. But I’ve always maintained that it’s a great place to visit on vacation and now that I’m older, also not a bad place to live (I always wanted to live in NYC growing up).

3) Winchester, Virginia

At first I wasn’t too sure about Winchester, VA but it grew on me after the Shenandoah Valley Apple Harvest Festival where we met a few very cool folks and were invited home for dinner by one couple. It’s not a terrible distance to D.C. either for a day trip. But a highlight was all the great wineries in that area including Barrel Oak Winery.

4) Waterbury, Vermont

I love the Waterbury area. It’s beautiful, centrally located and I love ice cream, so the fact that Ben and Jerry’s is based there just improves it exponentially.

5) Rainelle, West Virginia

Bridge Day was really fun, but I can imagine that the area is even more beautiful in the spring and summer. Given that I loved the area so much in the damp fall weather tells me this could be a great place to head back to in better weather.

6) Lexington, Kentucky

I really enjoyed a fair bit of Kentucky, but the relationships we made in Lexington with Nini at Harkness Edwards Vineyards and with Maggie at kayaking made it better than most locations. I also particularly liked Old Friend’s Farm for retired horses.

7) Brandon, Vermont

The area was ideally located to access the Middlebury Tasting Trail which was fantastic. The accommodation was reasonably priced which meant we were better able to enjoy the area. I also loved Warren Falls nearby.

8) Knoxville, Tennessee

I loved the things in proximity to Knoxville, TN even though we didn’t get to do much right nearby. I really loved the llama trek about an hour away.

9) Ness City, Kansas

I loved the Airbnb we stayed at and the welcome we received from our host. I was surprisingly pleased with Kansas overall, but Ness City was very pretty.

10) London, Kentucky

There was great hiking and great food in London, KY. Plus you can see three states in one spot only an hour from London.