Twenty years ago, Greenville, South Carolina, might not have been on your radar for a long weekend getaway. But over the past two decades, this vibrant city has emerged as one of the biggest small cities in the South, blending a nationally recognized food scene, thriving arts and culture, and stunning outdoor spaces. Best of all, it’s less than a five-hour drive from anywhere in the Triangle, making it a perfect driveable destination for a refreshing escape. Whether you’re looking for a culinary adventure, unique shopping, live entertainment, or outdoor exploration, Greenville delivers. While this three-day itinerary offers great ways to experience the city this spring, there’s so much more to explore – from charming boutique hotels and independent restaurants to hidden gems tucked throughout town.

DAY 1

As you arrive downtown and turn onto Main Street, the first thing you’ll likely notice is just how green Greenville is. With trees lining the sidewalks, the city center feels like a serene oasis with pedestrians roaming the oversized sidewalks, popping in and out of the boutiques and restaurants that welcome you into the town.

You’ll feel like you’re stepping back in time when you check in to the Westin Poinsett, which celebrates 100 years this June. When the Poinsett Hotel opened in 1925, it was one of the most beautifully furnished hotels in the country. Named for Greenville statesman Joel R. Poinsett (who introduced the red plant synonymous with Christmas to the United States), the hotel has been the centerpiece of downtown Greenville ever since.

Drop your bags and head out the front door to explore Main Street. Stop into M. Judson Booksellers to peruse the shelves lined with books, many from regional authors. Don’t overlook Camilla Kitchen, tucked inside the independent bookstore, where Chef Teryi Youngblood pours her heart and soul into each of the snacks and sweets. If it’s “Golden Hour” (after 4:00 PM), the small bites menu is the perfect means to hold you over before more exploring.

No visit is complete without a stroll through Falls Park on the Reedy. As many as 24,000 flowers are planted in the 32-acre urban oasis each year. Take a moment to watch the Reedy River waterfalls crash beneath you and find yourself surrounded by nature in the middle of downtown. Be sure to find Dale Chihuly’s sculpture, Rose Crystal Tower, located at the park’s West End entrance. It’s one of more than 120 pieces of public art throughout the city.

Your hardest decision all day will be where to eat dinner, as down-town Greenville boasts more than 200 independent restaurants. Jianna is just outside the main entrance to Falls Park. You’ll know it when you see the light blue chairs on the second-floor outdoor patio overlooking Main Street, the best seats in town! Inside, Chef Michael Kramer is extruding pastas by hand and serving up modern Italian dishes and raw oysters. And after dinner, head to Group Therapy for some fun; each hole of their indoor miniature golf course is uniquely designed for both nostalgia and challenge. Try your hand at ice curling, axe throwing, or the new golf simulators for more fun before turning in for the night.

DAY 2

Start your morning at Sully’s Steamers, known for their over-the-top steamed bagel sandwiches – a Greenville staple. Then, channel your inner chef with a hands-on cooking class at The Cook’s Station. Classes range from Southern comfort classics like biscuits and gravy to international cuisine like Asian fusion. After you’ve sharpened your skills, head downstairs to explore their massive kitchen shop, a boutique dedicated to all things cooking where you’ll find every gadget and tool you never realized you needed.

Continue your retail therapy by exploring some of the other downtown boutiques. Find the penny candy barrels at Mast General Store, taste dozens of on-tap oils and vinegars at Oil & Vinegar, and find the perfect gift at Samantha Grace Designs before stopping by Greenville Soy Candle. Candle-making classes are offered regularly, and you’ll select everything from the scent to the color before hand-pouring your own candle.

For a DIY history lesson, take a tour of Greenville via Eugenia Duke’s Unofficial Guide to Greenville. Greenville’s story as it relates to Duke’s Mayonnaise is legendary. In 1917, Eugenia Duke began selling homemade sandwiches to help make money for her family during the war. Due to requests from soldiers at nearby Camp Sevier just outside the city, she started bottling her mayonnaise around 1923. The mayo trail includes 20 of the tastiest dishes in town featuring the condiment, plus four historical stops.

Plan to spend the rest of the afternoon and evening in The Village of West Greenville, the creative hub that reflects the city’s growth over the past decade. Stop in the Greenville Center for Creative Arts, located in a former mill, to enjoy their latest exhibition. Then head over to Poe West where you can take the tour at Six & Twenty Distillery to observe how they craft their spirits by hand using locally grown grains, enjoy a beer flight at Carolina Bauernhaus, or a chocolate and wine tasting at La Rue Fine Chocolates.

For dinner, experience The Anchorage, a James Beard Best New Restaurant Semifinalist that takes farm-to-table dining to the next

level. Many of The Anchorage’s ingredients are sourced from Horseshoe Farm, which was started by the restaurant’s first Executive Chef and local farmer, Chris Miller.

Cap off the evening with dessert and drinks at Carmella’s Dessert Bar & Café, the perfect spot to wind down with decadent cakes and a surprisingly extensive cocktail and wine list. For a livelier night scene, head to Juniper. Located on the roof of the AC Hotel, this massive Instagram-worthy bar restaurant offers stunning views of downtown and equally as interesting cocktails, along with a full Zero-Proof menu.

DAY 3

Kick off your final morning with a cold-pressed juice or açaí energy bowl from Southern Pressed Juicery before heading off to Reedy Rides to rent a bike or e-bike. Head out on the Prisma Swamp Rabbit Trail, which starts in downtown Greenville and runs out of town through the beautiful Furman University campus and into the small neighboring town of Travelers Rest. Along the way, you’ll see coffee shops, restaurants, breweries, and people galore. The mostly flat trail welcomes cyclists and pedestrians of all skill levels.

Once you’ve enjoyed your two-wheel experience, head to Heritage Green where you can delve into the past at the Upcountry History Museum, view important works by Andrew Wyeth and Jasper Johns at the Greenville County Museum of Art, and enjoy interactive exhibits that celebrate music through the ages at the Sigal Music Museum. Before heading home, grab a bite at brewery Fireforge Crafted Beer, where the patio is always full of activity from live music or a special event.

Whether you’re drawn to Greenville’s booming food scene, its thriving arts community, or its scenic outdoor spaces, this three-day itinerary is just the beginning. With countless restaurants, shops, museums, and hidden gems to discover, you could visit multiple times and never have the same experience twice. So why not make your next quick and easy getaway – whether it’s a romantic weekend, a foodie escape, or an outdoor adventure – one to remember? Less than five hours away, Greenville offers a perfect balance of southern charm and modern energy, making for an unforgettable long-weekend destination that’s well worth the drive.

For more ideas and travel inspiration, visit VisitGreenvilleSC.com.

Photo courtesy of VisitGreenvilleSC.com.