A Weekend Getaway to Winston-Salem, NC: The Coolest Hyphenated City in the South

Old Salem: Winston-Salemites, would prefer that you not refer to Old Salem as the “mini-Williamsburg (VA),” but if that helps present a mental picture for you, then that’s ok by me. Old Salem is a living history museum that takes you back in time to the 18th Century. Visitors can experience the distinctive culture of the Moravian settlers and explore their squares, homes, gardens and workshops. Make sure to grab a coffee and traditional sweets at Lot 63.

NCMA - Winston-Salem: Nestled on the scenic Hanes estate (if you are thinking underwear brand, that’s the one), the NCMA Winston-Salem is a prime example of the past meets present vibe of Winston-Salem. The former SECCA is a historic home with a modern wing where you can experience contemporary art and culture both inside and outside on the expansive grounds.

Reynolda House & Gardens & Village: Winston-Salem didn’t just originate in Hanes. The Reynolds tobacco family grew out of the soil, too. One of their family estates is right down the street from NCMA-WS. Meander through two miles of wooded trails, stroll the formal Gardens and enjoy the charming shops and restaurants in Reynolda Village. Ticketed admission to the historic house will allow you to walk through the rooms bursting with impressive American art and fashion. Keep your eye out for the indoor pool and bowling alley.

Discover Downtown: Downtown Winston-Salem blends a rich history, showcased in beautifully preserved Art Deco buildings, brutalist architectural structures and turn-of-the 21st century modern skyscrapers. Former tobacco warehouses turned into lofts, a thriving arts scene, several green spaces and a brand-new children’s museum have revitalized downtown and transformed it into a dynamic destination for any visitor. Head over to Trade Street for some shopping at Fancy Groceries, Mast General Store and Visual Index.

Urban Nature Break: Tucked in between the historic estates off Reynolda Road and Downtown, don’t miss an opportunity to have a countryside experience in the heart of Winston-Salem. Bring your hiking shoes for an up to 3-mile walk on the Stuart & Emma Thomas Memorial Trail. Offering trails through rolling pastures, hills and forests, hikers will also appreciate scenic city skyline views and maybe come across a grazing cow or two.

Pilot Mountain State Park: If you look off into the distance to the northwest, it’s hard to miss the geologic phenomenon that is Pilot Mountain. Located 20 miles away from Winston-Salem, Pilot Mountain centers around the iconic knob that has served as a navigational beacon since the Saura Native Americans lived in proximity. Nowadays, there are numerous trails for hiking and horseback riding, as well as rock climbing spots and overnight camping.

Stand Up Paddle at Salem Lake: Triad Eco Adventures has several SUP tours available on Salem Lake, located on the east side of Winston-Salem, for those looking for some “active”ities. It’s a picturesque lake with a paved trail running seven miles around the lake (for those who don’t want to be on the water). It’s a gathering spot for local anglers, distance runners and mountain bikers as well as ducks and geese.

Bobby Boy Bakeshop: Owners John and Lucia Bobby have stints in much-admired kitchens around the world. Now they have one of their own artisanal bakeshops in the Buena Vista neighborhood of Winston-Salem. Featuring pastries and baked breads that taste as good as they photograph, Bobby Boy often has lines out the door. It’s a special treat after a walk across the street on the Thomas Trail.

La Victoria: Head to the back of the La Victoria Grocery and Meat Market for an authentic Mexican lunch. This gem includes large portions, homemade tortillas and a salsa bar for all spice levels. The Ques birria is worth the extra wait.

PBs Takeout: A local favorite since 1987, you’ll have to sit inside at the small counter area or outside on the picnic tables to savor the hot dogs on toasted buns spread with buttery goodness with a side of crispy fries and homemade chili.

Lexington BBQ: Head 20 miles South on US 52 to the town of Lexington, home of the “True Western-Style Carolina BBQ.” Nationally recognized Lexington BBQ cooks their barbeque slowly over wood coals, not gas and only serves the pork shoulder. Order a Cheerwine or Sweet Tea with your BBQ plate and save room for their Peach Cobbler.

Mission Pizza Napoletana: MPN’s menu rotates with frequency and features a precise selection of small plates and entrees, pasta and pizza Napoletana, often pulled from the brick oven by owner Peyton Smith. MPN has a slim but superb wine list, often featuring wines from small Italian producers. Reservations are strongly encouraged.

The Caviste: The Caviste is a local wine bar and bottle shop that specializes in small estate producers from all over the world. Grab a seat at the bar for a glass of wine and some bar snacks, prepared by the team at Bobby Boy Bakeshop. They share the same building and often present special wine dinners together. Make sure to check out The Caviste on Instagram to see their daily bar snack menu and wine specials.

Mozelle’s: On a busy corner in the West End neighborhood, Mozelle’s is a modern southern bistro serving tasty favorites like tomato pie, shrimp and grits and fried chicken. Sit outside along the street during warmer weather and inside for a cozier, swanky diner-like vibe in the cooler months. Also, a great spot for Sunday brunch.

Little Pep: Newest to the scene, Little Pep is a welcome addition to Trade Street and the arts district. With a design-friendly vibe, you’ll feel like you stepped into a European wine bar to enjoy small plates and natural wines. Their signature merch and assorted pantry goods make perfect souvenirs or gifts for your house, dog or babysitter.

Easy Talk: An all-day beverage spot, come at night for the drinks. Cocktails are enjoyed downstairs with a consistently changing menu of eight core cocktails in their “easy” bar. Upstairs in their more sophisticated “talk” bar, you’ll enjoy a bespoke drinking experience of finely crafted cocktails and conversation. Grab a bag of imported Lays chips to snack on, spice it up with one of the more exotic flavors.