chicago to asheville, greenville & wilmington – a road trip guide

After a long hiatus of not being able to travel, we were desperate for a change of scenery and planned a short road trip to visit friends in North Carolina and South Carolina at the end of the summer. What ended up being a two week trip, could have easily been extended for longer and we loved every city we visited.

wrightsville beach in wilmington

asheville

Our first leg of the trip, Chicago to Asheville, was only a 10 hour drive. The route we took through Indianapolis, Louisville and Knoxville, meant plenty of cities to stop for coffee, lunch or a snack to avoid fast food off the highway.

We only planned to stay for one night before heading to Greenville the following day, so we stayed at the Foundry Hotel, which is a Curio Collection by Hilton hotel. It’s in an incredible location, walking distance to downtown, the South Slope Brewing District and the River Arts District.

the foundry hotel in asheville

We were blown away by Asheville. So much so, that we stopped again on our way home at the end of the trip. Not surprisingly, goop named Asheville one of the four most underrated American food cities. While a lot of the top restaurants were closed due to the pandemic or booked with limited indoor seating, we have a list of places to try next time we visit.

the antidote bar in asheville

For a full recap on Asheville and each spot we visited, check out my Asheville guide here.

farewell coffee in asheville

things we loved in asheville

start your first morning off with coffee at farewell and a walk around the brewery and arts districts

pick up picnic supplies or gifts at south slope cheese co.

try every single donut at hole doughnuts (don’t bother with vortex doughnuts)

grab chai pani for lunch and try not to crave it for the next meal

enjoy a cocktail or two at the antidote bar

settle in for a flight of beers at wicked weed brewing’s funkatorium

hole doughnuts in asheville
wicked weed funkatorium in asheville

places we wanted to try

grab a to go picnic set from the rhu

try a beer at green man brewery, twin leaf brewery or any of the dozens of other breweries nearby

visit sovereign remedies, rhubarb or gan shan west for cocktails and date night

cap the night off at the montford, a downtown rooftop bar

chai pani in asheville

 greenville

After our quick overnight in Asheville, we hit the road for Greenville to visit our friends, Shawn and Laura, and their new baby girl, Eliza.

We arrived in Greenville on a Friday, spending the beautiful weather weekend downtown at their favorite spots. The rest of the week, we found so many great remote working spots and could’ve worked remotely from them for weeks.

gather greenville

You’ll probably find Greenville on a ton of lists for great cities to visit and move to and we love exploring all of the surrounding areas in addition to downtown.

Years prior, Kevin and I visited Greenville for Shawn and Laura’s wedding, so a few of the places below are from that trip, but still stand as solid Greenville options.

For a full recap on Greenville, check out my Greenville guide here.

methodical coffee in greenville
fork and plough in greenville
the village grind in greenville

places we loved in greenville

enjoy a local, farm to table dinner at fork and plough

spend the afternoon outside at gather greenville

grab a coffee or work remotely from methodical coffee or the village grind

pick up a few designer staples at augusta twenty

splurge on date night at jianna

grab a thaiPA or blood orange wit from fireforge crafted beer

take advantage of bogo açaí bowls from southern pressed juicery

fireforge crafted beer in greenville
gather greenville
downtown greenville

wilmington

After spending almost a week in Greenville, it was time to make our way to the coast.

When planning the trip, we wanted to avoid staying in hotels for a long period of time due to the pandemic and stretch our travel budget for a two week trip. Our friends, Austin and Christian, live in Wilmington, so it was the perfect second destination of our trip.

If we’re being honest, we had low expectations, thinking Wilmington was going to be a typical, coastal beach town. We were proven SO wrong and absolutely loved the vibes of downtown and the wide range of restaurants and coffeeshops. Our friends were also the best hosts, filling our days with active activities and off the beaten path spots around the city.

downtown wilmington
edward teach brewing in downtown wilmington

As you’ll see the below list is so full of solid recommendations and our friends had even more that we had to skip because of timing or COVID closures. We can’t wait to go back!

For a full Wilmington recap, check out the Wilmington guide here.

our favorite wilmington activities

start your workday by grabbing coffee at drift or social coffee supply

grab coffee from the workshop and go paddle boarding at sunrise

treat yourself to an açai bowl at zeke’s post-paddle boarding

visit sundays and take your coffee and breakfast to the beach

the jetty bar on wrightsville beach

enjoy the sunset and a cocktail at the jetty bar at oceanic before having dinner at ceviche’s

taste a few beers at palate before grabbing a few local bottles to go

settle in for a pint of teach’s peaches and games at edward teach brewing

walk around downtown and grab lunch at the copper penny

try not to spend all of your money on the decor and furniture at threve mercantile

threve mercantile in downtown wilmington
the outpost in wilmington

stop by the outpost for an afternoon beer in the sun

opt for a mouthwatering thai and vietnamese dinner at indochine

palate bottle shop in downtown wilmington

As our trip came to an end and we drove back to Chicago, we kept reminiscing on how fun road trips are and couldn’t wait to plan the next one. While flying post-pandemic will be easier, it was so nice to map our own routes, stops and take our time along the way. While we plan the next one, what routes have you taken that made you love road trips again? West coast is definitely high up on our list.

Leave a Reply

Your email address will not be published. Required fields are marked *