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Graylyn Estate
Stay at this 1920s country estate and feel as though you're in a movie. Graylyn Estate covers 55 acres just 10 minutes from downtown, so you can reach the city easily but won’t hear it. For the full royalty experience, request one of the antique guest rooms in the Manor House, which were once the Gray family’s bedrooms and sitting rooms. Dress up for dinner in the formal dining room, or try for breakfast in the Persian Card Room, said to have been the Grays’ favorite place for entertaining. Not staying the night? The Manor House dining room is open to the public for lunch and dinner, and the monthly Tour Pour du Jour adds a butler-led tour with wine and appetizers.
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Other accommodation ideas
Reynolda House and Gardens
Katharine and RJ Reynolds completed this sprawling home in 1917, and the bungalow now houses a collection of American art. Look for the lion’s feet in the Reception Hall, then head upstairs to the second-floor bedroom galleries. Outside, the gardens unfold along winding paths and over stone bridges toward an iconic greenhouse. Then follow the walking trail across the Lake Katharine Bridge for a view of Reynolda’s waterfall. You could even bring along a picnic if you're bundled for the weather. Don't miss nearby Reynolda Village, where charming local shops and restaurants fill the estate’s former auxiliary buildings.
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Get the Reynolda Village shopping guide
Old Salem Museum & Gardens
German-speaking Moravians founded Salem in 1766, and today their village unfolds across nearly 100 acres of costumed interpreters, working trade shops, heirloom gardens and centuries-old buildings. Begin at the visitors center and stroll across the covered Heritage Bridge, one of the most romantic spots in Winston-Salem, especially when glowing Moravian stars line the way during the holidays. Linger in the award-winning garden behind the 1769 Single Brothers House, then head to Winkler Bakery. Open since 1799, it is the oldest operating bakery in the country, still turning out Moravian sweets and Lovefeast buns. Peek at the original beehive oven, then head upstairs to Winkler Book & Gift for locally made candles and ornaments.
Walnut and Broad
Walnut & Broad sits where the historic Old Salem, West Salem and Washington Park neighborhoods meet, and the redevelopment kept the buildings’ distinctive historic character. The anchor is East of Texas, a concept from local restaurateur Claire Calvin that serves Tex-Mex barbecue. Next door is easytalk, from the team behind Ginger Fox. It handles everything from custom cocktails to coffee and fresh sodas, and it even offers cocktail classes so you can up your mixology skills. That makes it just as good for a slow morning latte as for an evening drink. Make it the final stop after a day wandering in Old Salem.
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Find easytalk cocktail classes
The Arts District
Winston-Salem’s creative spirit is on full display in the Downtown Arts District, which runs along Trade and Liberty streets between Fifth and Seventh, packed with galleries and boutiques selling local apparel, vintage pieces and original art. The cornerstone is Piedmont Craftsmen Gallery, which represents nearly 400 of the country’s finest craft artists and sells handmade goods. A few steps away, Fancy Groceries offers a more personal kind of shopping for gentlemen, with its own coffee bar to fuel your browsing. For a gift that will spark your memory, stop by Kin & Cottage, where candles and incense carry Southern scents like Spanish Moss and Appalachia.
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Get your Arts District shopping guide
Earl’s Restaurant & Bar
Earl’s Restaurant & Bar sits in downtown’s Industry Hill, a neighborhood that was once home to furniture factories, tobacco warehouses and produce dealers, and it's grown into a hub for makers, creatives and entertainers. Earl’s fits right into that spirit with a lively atmosphere, top-notch whiskey bar, authentic Southern fare and live music. Grab a seat near the stage and share a round, whether you’re out with your favorite person or your whole crew. Earl’s also makes an easy first or last stop for a bigger night out since it's just steps away from The Ramkat, an intimate live music venue.
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Keep the night going at these Winston-Salem spots
Bookmarks
Downtown Winston-Salem is made for an unhurried afternoon of browsing. Start at Bookmarks, a literary arts nonprofit and independent bookstore that opened in the renovated Nash building in 2017. Inside, cozy nooks with comfortable chairs invite you to settle in with coffee and conversation. Try a sweet bookstore ritual: Split up, have each person choose a book for another, and then swap over coffee. Your purchase also does some good, since the store reinvests its proceeds in community outreach. Next door is Design Archives Vintage and Handmade Emporium, where individual makers and curators each run their own mini booths. The mix is equal parts vintage clothing, retro decor and boho gifts.
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Browse more local shops and boutiques
a/perture cinema
Up for a night out with some indie charm? Head to a/perture cinema, Winston-Salem's independent, locally owned movie theater. Since opening in 2010, this intimate four-screen nonprofit has built a loyal following for its programming, so you can't miss this spot if you're a film lover. The lineup mixes first-run indies, international releases and festival favorites. Whether you choose to enjoy a matinee or catch a late showing, a/perture is downtown right in the middle of it all, which makes choosing your next scene even easier.
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Explore dining options downtownLittle Pep
For a romantic meal or nightcap after catching a film, pop by Little Pep. Tucked into downtown’s Arts District, Little Pep is a cozy wine bar and shop that delivers on modern ambiance and hospitality. The focus here is natural, low-intervention wines and small plates, paired with an ever-changing menu built around local and seasonal ingredients. Drop in for chic snack, order several plates and make a meal of it, or even grab a bottle to take home.
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Sip through Winston-Salem's nearby wineries
Tanglewood Park
When winter comes, Tanglewood Park turns into one of NC’s most beloved holiday traditions. About 10 miles west of downtown Winston-Salem, this stunning display is built on a 5.1-mile route that winds past 80 unique displays lit by more than a million lights. Most visitors drive the route, but the most magical way to see it is cozied up in a horse-drawn carriage. Tanglewood’s stables offer these highly sought-after rides in a traditional white carriage with room for you and up to three guests. After the ride, stop at the Red Barn, where you can browse gifts and roast marshmallows over firepits.