The season takes on a timeless glow at Old Salem Museums & Gardens, where costumed interpreters, candlelit streets, and the warm aromas of Moravian sugar cake and crisp spice cookies invite groups to step straight into centuries-old holiday traditions. With a single ticket, visitors can spend several unhurried hours exploring this nearly one-mile-long living-history museum from historic trade shops and heirloom gardens to the acclaimed Museum of Early Southern Decorative Arts (MESDA), celebrated for its extraordinary collection of Southern fine art, furniture, and craftsmanship. Don’t miss the beloved Heritage Bridge, a favorite holiday photo spot that twinkles under the Moravian stars and frames the perfect keepsake of a day steeped in history. Dive deeper into the history of the area at Historic Bethabara Park with their Christmas at Bethabara celebrations.

No holiday visit is complete without Moravian cookies: delicate, paper-thin, and baked with generations of tradition. At Mrs. Hanes’ Moravian Cookies, groups can tour the bakery and watch as cookies are still hand-rolled and cut by “the artists in aprons,” just as they’ve been for more than 60 years. At Wilkerson Bakery, this family owned and operated baking dynasty still bakes Moravian sugar cake fresh daily, filling the air with the aroma of Christmas past. And at Dewey’s Bakery, a Winston-Salem institution since 1930, groups can stock up on Moravian sugar cake, crisps, and other holiday favorites that make perfect stocking stuffers—available year-round. 

The history continues at Reynolda, the former estate of R.J. and Katharine Reynolds, where holiday exhibits and seasonal décor fill both the Reynolda House Museum of American Art and the boutique shopping of Reynolda Village.  Donned with boughs of holly and red ribbons galore, Christmas at Reynolda is a wonderous time to tour the historic house and its array of exhibits. Groups can cap off a visit with a bite to eat at one of the Village’s cozy cafés or restaurants. 

For a quieter moment, Reynolda Gardens offers a peaceful retreat. Winter light glows across formal gardens and wooded trails, creating a natural pause in the bustle of the season. Combined with nearby shopping and dining in Reynolda Village, groups can enjoy two experiences in one outing—another win-win for your itinerary. For a grand finale, see the grandeur of the Graylyn Estate, opening their storied doors with guided butler tours that offer a glimpse into Winston-Salem’s gracious hospitality in a setting dressed for the season.

Winston-Salem shines as a shopping destination, especially during the holiday season. A stroll through the Downtown Arts District offers gallery hopping and handcrafted finds at Piedmont Craftsmen’s Gallery, where artists from across the country are represented. Throughout the district, you can find an array of dining options and outdoor spaces, like the inspired Artivity on the Green Park that sits adjacent to Red Dog Gallery and Chad's Chai Tea House. 

Every year, the weekend after Thanksgiving, the Benton Convention Center fills to the brim with artists, woodworkers, artisans, and other makers for the annual Piedmont Craftsmen Fair. The southeast's premier holiday showcase of art, this weekend is not one to be missed for early holiday shopping and unique finds. Throughout the season, local art markets pop up around the city perfect for exploring, such as Angelo's Artisan Market, The Firefly Market, The Holiday Atrium Market, and the Sawtooth Holiday Market and Juried Exhibition.

Expand your group’s experience by adding a shopping excursion to include the Reynolda Road Shopping District with its boutiques and specialty shops, the Stratford Road Shopping District with its mix of national retailers and local gems, and the historic West End neighborhood, where you’ll uncover charming stores and unique treasures.

No holiday tour in Winston-Salem is complete without a drive through the Tanglewood Festival of Lights, one of the largest light shows in the Southeast. More than a million twinkling bulbs line winding park roads, creating dazzling displays that wow first-timers and repeat visitors alike. 

Pair the lights with a stop at the on-site town square for a mug of hot cocoa, holiday décor, and shopping for locally made goods, and your group will leave glowing inside and out. 

There’s magic in making something with your own hands. At Sawtooth School for Visual Art, your group can design personalized gifts such as ornaments, ceramics, or even handmade jewelry that become treasured keepsakes. Pair that with our team’s planning, and you’ll find it easy to build a meaningful, hands-on moment right into your holiday tour.

To book a group tour experience- during the holidays or any other season- contact Kay Calzolari, Senior Group Tour & Services Manager!