5-Day Roadtrip from Washington D.C. to Greenville, South Carolina.

I did the most unusual roadtrip earlier this year for work.

I had to drive from our office in Washington D.C. down to Greenville, in South Carolina, stopping off at Lynchburg in Virginia for two nights enroute.

It was while I was working at Amazon, so I was there to visit two of our largest sellers, and follow one of them as they moved warehouses to a different state.

It was super cool and I managed to see and do a little bit in the local areas in the evenings and on the weekend, so I wanted to take you through how you can do this slightly unusual but fun roadtrip!

Two Nights in Washington D.C.,Virginia

Stay at: St Regis Washington D.C.

My roadtrip started in Washington D.C., as I needed to go into our Arlington office to meet some of my colleagues in-person.

I recommend staying at the St Regis Washington D.C., undoubtedly one of the most luxurious hotels in the city, and the perfect position to see all the main sights.

If you need something more mid-range, Moxy Washington D.C. is also great – the Moxy brand is one of my favourites in Marriott’s portfolio!

Things to do in Washington D.C.

My colleagues gave me some great tips about where to go and what to see in Washington D.C., as well as Lynchburg and South Carolina as well! I was also very fortunate that one of my colleagues took me for a fancy dinner and drinks in the city on my second night in D.C., which was so much fun!

Although I was working most of the time, because of the jetlag I woke up crazy early in the morning so had a few hours to actually explore the city.

I started with a delicious classic diner breakfast Bob & Edith’s diner in Arlington, then got an Uber over to Lincoln Memorial and started my walk there.

Seeing Lincoln Memorial in person was so wild. Like I couldn’t believe I was actually there?! It felt so humbling.

Also, you know how in political action movies set in D.C., you always see people jogging in the park? WELL IT ACTUALLY HAPPENS. There were actually joggers eeeeverywhere!

After Lincoln Memorial I walked along the reflecting pool, and up through the park towards the WW2 memorial and Washington Monument.

What struck me, was how quiet it was in the park? There’s a huge ring-road going around the outside, and yet the trees blocked out all the traffic noise.

It’s at Washington Monument that you can divert to your left and walk over to The White House. But, the St Regis is opposite the White House, so if you stay there you can see it any time you leave the hotel.

From there, continue your walk through The National Mall park and up towards the State Capitol building.

From there, head to Sonoma Restaurant and Wine Bar for lunch. It’s a super cute restaurant that specialises in local, fresh and sustainable ingredients.

While I had to work in the afternoon, you can check out the nearby museums: the National Museum of African American History and Culture, the National Museum of Womens in the Arts, and the Smithsonian National Air & Space Museum. Then get an Uber over to Arlington Cemetery to pay your respects to President John F. Kennedy.

Enjoy pre-dinner drinks at Zaytinya by José Andrés. Their Mediterranean-inspired cocktails are incredible!! I loved the ‘Pomono’, which was a combination of Ouzo, lemon, pomegranate, and Moroccan mint.

Book a table at Cranes, a restaurant and sake lounge focusing on Japanese x Spanish cuisine, for dinner. This beautifully designed restaurant has a super interesting menu and my colleague and I really loved their tasting menu and cocktails (total bill was around $150 per person, but it was 100% worth it).

Finish the evening with drinks at Old Ebbitt Grill round the corner from the St Regis.

Best Things to do in Washington D.C.:

  • Breakfast at Bob & Edith’s diner
  • Lincoln Memorial
  • Lincoln Memorial Reflecting Pool
  • White House
  • Washington Monument
  • State Capitol
  • Lynch at Sonoma Restaurant and Wine Bar
  • JFK Grave at Arlington Cemetery
  • National Museum of African American History and Culture
  • Smithsonian National Air & Space Museum
  • Cranes Japanese restaurant
  • Drinks at Old Ebbitt Grill

Drive to Culpeper, Virginia

Pick up your hire car in D.C., and start your roadtrip by driving down towards Lynchburg, Virginia.

Stop off in Culpeper enroute to stretch your legs and see this adorable town! I LOVED Culpeper, despite only walking around the streets as everything was closed (I arrived around 5pm in the evening).

It’s this ridiculously cute tiny little town, with stereotypical American streets – if you close your eyes and imagine a small town in America in the 1940s, this is what will come to your mind.

Then, continue driving until you get to Lynchburg.

One Night in Lynchburg, Virginia

Stay at: Craddock Terry hotel

Every colleague who knew I had to go to Lynchburg told me how sorry they were, and even the sellers told me it’s not a great place and that’s why they’re moving, so I was shocked – *shocked* – to find I really liked it, haha.

I also loved the hotel I stayed at, the Craddock Terry Hotel, which is a Marriott Tribute Portfolio hotel. In 1888, The Craddock Terry Shoe Company was founded in Lynchburg by John W. Craddock, and grew into the 5th largest shoe company in the world.

Craddock Terry Hotel Lyncburg Exterior

The hotel is housed inside their old shoe factory, and the property has been tastefully renovated around the shoe theme.

During the renovation they managed to retain the original industrial feel by exposing the wood beam ceilings, brick, stone exterior walls, and nine-foot-tall windows. Book a stay at the Craddock Terry!

Things to do in Lynchburg, Virginia

Don’t get me wrong, it’s a random little town and you really only need one night there, but it’s fairly cute, had great food, fun street art on Art Alley, and beautiful views from the LU Monogram. You should also visit the American Civil War Museum while you’re there.

Food-wise, make sure you stop by My Dog’s Diner for breakfast, and Bootleggers for dinner. I had the best burger of my life at Bootleggers. And when I say the best, I mean the best. It was absolutely insane.

Burger and ice-cream at Bootleggers, Lynchburg VA

Best Things to do in Lynchburg:

  • LU monogram
  • Lynchburg Museum
  • Monument Terrace
  • Amazement Square
  • Viewpoint at River Front Park
  • Street Art on Art Alley on 11th Street
  • American Civil War Museum
  • Breakfast at My Dog’s Diner
  • Burgers at Bootleggers

Stop off in Charlotte, North Carolina

Now, you’re gonna drive from Lynchburg to Greenville in South Carolina. But if you have some extra time you can stay overnight in Charlotte and really explore the city!

I personally just stopped off their for lunch on my way from Lynchburg to Greenville, as I didn’t have time to stay overnight.

From what I could see it’s just your standard American city, but one of my colleagues recommended I visit Optimist Hall, and I really, really loved it!

It’s very similar to Meracto Mayfair and Victoria Market Halls in London, but much nicer and bigger.

Optimist Hall has over twenty food stalls, three dine-in restaurants, a craft cocktail lounge, plus a whole load of adorable retail shops.

They even have a brewery on-site!

It was the perfect place to stop-off at because it was on the edge of the city and had a large car park next to it. I also loved all the choices of food and drink.

I was a little devastated though because I was still ridiculously full from my iHop breakfast, so I just got a green juice. It was an incredible green juice though!

Two Nights in Greenville, South Carolina

Stay at: The Westin Poinsett

Check-in at The Westin Poinsett and spend two nights there to explore Greenville!

Greenville is a beautiful town in South Carolina with lots to see and do in the local area. There are dozens of parks, trails and other nature spots to walk and cycle, and plenty of museums too.

Stay at The Westin Poinsett, a beautiful luxury hotel in the heart of the city. There aren’t many luxury hotels in Greenville, so The Westin is definitely the best option, and it’s super easy to get around and see everything from the hotel’s central location. Book a stay at The Westin Poinsett! 

Things to do in Greenville, South Carolina

Make sure you go to Liberty Bridge to see the Reedy River Falls, before exploring Falls Park itself. The Downtown Trolley tour is a great way to see the city, I went on one of these in Salt Lake City as well and it was so much fun.

The town is packed with history. Museum-wise you can visit the Greenville County Museum of Art and the Upcountry History Museum, the Kilgore-Lewis House, and the History Museum of Travelers Rest, which previously operated as a grocery store in the 1920s.

Greenville is also a foodie hotspot with the most incredible restaurants and bars!

Food-wise, you need to go to Soby’s in the centre of Greenville, and Fork and Plough further out towards Greer for dinner. Both are just amazing and were some of the best food I’ve ever had in the US (and I’ve visited 22 states now).

Soby’s offers ‘new south’ cuisine, so I enjoyed a Peach Mule, Fried green tomatoes, Fried chicken cooked in hot honey and served with broccolini and black truffle mac & cheese, and then I finished with their famous White chocolate and banana pie!

The whole meal was out-of-this-world good. Just make sure you book in advance (or be prepared to sit up at the bar).

We then went to Fork & Plough for dinner with one of our Amazon sellers, and it was the cutest neighbourhood restaurant, market and butchery that specialises in local ingredients. The menu changes twice a day because everything is local and regional, so it depends on what they have in that day. We got a variety of dishes and everything was incredible!

Finish your evenings at Jack n Diane’s bar (note: you might have to queue, and there is a small cover charge), where you can watch the dueling piano performances and join in with the singing. This was a recommendation direct from our seller!

It’s such a vibe and my colleague and I loved this place! Make sure you get the Key Lime Pie martini – it’s heaven.

Best Things to do in Greenville SC:

  • Falls Park on the Reedy & Liberty Bridge
  • Take the Downtown Trolley tour
  • Greenville County Museum of Art
  • Upcountry History Museum
  • Walk or cycle the Swamp Rabbit Trail
  • Art in Public Places Self-Guided Tour
  • Visit the Kilgore-Lewis House
  • History Museum of Travelers Rest
  • South Carolina Botanical Garden in Clemson SC
  • Dinner at Soby’s
  • Lunch or dinner at Fork and Plough
  • Cocktails at Jack n Diane’s dueling piano bar

The Most Random Roadtrip

Is this the most random roadtrip I’ve ever written about?! Absolutely. But even though I was working most of the time, it was so much fun and I loved seeing towns I would never usually visit on vacation!

I honestly think these areas are so underrated and I’d 100% recommend taking a roadtrip along this route for something a bit different.

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Catherine Lux
Catherine Lux

Catherine Lux is a veteran travel blogger by night and the Head of Content Marketing at Amazon by day. Originally from Surrey, she spent four years living in Australia (2007-2009, and 2016-2018), and now lives in London. An ex-party girl sometimes prone to relapses, she loves nothing more than sharing her fine dining and luxury travel experiences with her loyal readers.

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