Reynolda Village Holiday Stroll

Date(s): Nov. 23, 2–6 p.m.

Location: Reynolda Village

Get into the holiday spirit with a stroll through historic Reynolda Village. Shop for unique gifts at your favorite boutiques, savor a delicious meal at one of our many restaurants and enjoy the beautiful holiday décor inside and outside the shops. The event will also feature a festive mix of entertainment, from Victorian-era carolers and carriage rides to visits with Santa, making it a shopping experience for the whole family. While you’re there, stop by the newly reopened greenhouse at Reynolda Gardens. Now known as the Brown Family Conservatory, the greenhouse sells a variety of holiday gifts and plants, including poinsettias and Reynolda’s annual holiday ornament.

Piedmont Craftsmen Fair

Date(s): Nov. 23-24 (various times)

Location: Benton Convention Center

A beloved Winston-Salem tradition for over six decades, the Piedmont Craftsmen Fair returns to Benton Convention Center the weekend before Thanksgiving, Nov. 23-24. As always, the festival features nearly 100 of the Southeast's top artisans selling handcrafted items in various mediums, from stunning jewelry and home decor to functional art and keepsakes. Named "one of the Top 10 craft fairs in the country" by American Style Magazine, the event is the perfect way to kick off the holiday shopping season. Whether you’re hunting for that perfect present for the hard-to-shop-for friend or simply looking to add to your own collection, the fair is a treasure trove of possibilities. As a bonus, you'll have the chance to meet all of the craftsmen selling items, meaning every gift potentially comes with a personalized story.

Merry Makers Market in Kernersville

Date(s): Nov. 29-30, 10 a.m.–4 p.m.

Location: Ciener Botanical Garden

Celebrate Black Friday and Small Business Saturday at this annual event at Paul J. Ciener Botanical Gardens in Kernersville. Dozens of artisans, makers, and specialty vendors will be on hand, selling items inside and outside, giving you plenty of chances to find unique items you didn't know you needed. Hosted by Purple Wagon Events, the market will also feature food trucks, a gift wrap station, and plenty of holiday cheer.

Sawtooth Spotlight’s Holiday Market

Date(s): Dec. 7 | 11 a.m.–4 p.m.

Location: Sawtooth School

This holiday market pulls in artists from around the region to sell handmade items in the Milton Rhodes Center for the Arts. You’ll find various items from ceramics, jewelry, and textiles to paintings, photography, and woodworking crafts. There will also be hands-on activities and craft demonstrations during the market and food trucks in case you get hungry. Sawtooth’s Juried Exhibition will be going on during this time as well, so you can admire the high-quality work of many local artists. The event is open to all, with a suggested $5 donation to support scholarships and community outreach.

Can’t make the event? No worries. Sawtooth will be selling locally made holiday gifts throughout the season at their onsite shop and gallery.

Holiday Markets by Catbird Events

Date(s): Multiple, check their events page

Location: Varies

Catbird Events was created specifically to increase opportunities for people to support and shop at local businesses. They host various pop-up markets throughout November and December, where you’ll find a great selection of goods sold by local vendors. These markets are set up at local breweries, the Winston Junction Market, Hanes Mall, and more. While you get to support local vendors and finish your holiday shopping, you can also support the small businesses where these pop-up markets are held. Whether you’re looking for locally made art or handmade goods, you’ll find something unique at these events!

Holiday Market at ROAR

Date(s): Saturdays from Nov. 23 to Dec. 21, 11 a.m.–4 p.m.

Location: ROAR

This indoor market will be held at the popular entertainment venue, ROAR, in downtown Winston-Salem. Escape the cold and check out the vendor booths by local artists and makers. Once you’re done shopping, you can check out ROAR’s bowling alley, golf simulators, indoor blacklight putt-putt course, arcade, or grab a drink and gather on the dog-friendly lawn. They also host live music often and have one of Winston-Salem’s only rooftop bars, so look forward to a whole lot of holiday cheer! While downtown, you could also keep the holiday shopping going and check out some local shops within walking distance.

Christmas in the Coalpit

Date(s): Dec. 8 | 12–4 p.m.

Location: Incendiary Brewing

Right outside of Incendiary Brewing Company, in the historic Coalpit gathering space, there will be a holiday market with nearly three dozen local vendors. The Coalpit is part of Bailey Power Plant, which was built in 1947 to provide power for RJ Reynolds Tobacco. Now, Bailey Power Plant houses businesses like Incendiary Brewing, Cugino Forno Pizzeria, and Anchor Coffee Co. In addition to the vendors, there will be live music by William NeSmith and an opportunity for photos with Santa and Mrs. Claus. This is a family and pet-friendly event, so come out for some great shopping and maybe grab a beer at Incendiary while you’re at it!

Village Holiday Market (Kernersville)

Date(s): Dec. 14 | 9 a.m.–1 p.m.

Location: Ciener Botanical Garden

Hosted by Village Family Chiropractic at the beautiful Kernersville Botanical Gardens, this will be a fun event with over 15 local vendors. In addition to the local artisans, you can get free pictures done with Santa by Thistle Weeds Photography. Free Christmas cookies will also be available, and The Given Coffee Truck will be selling coffee and cocoa there. All proceeds made by The Given Coffee Truck will be given back to the community. There are plenty of things to do on a day trip to Kernersville, so make a full day out of it if you’d like. Be sure to check out the multiple boutiques downtown where you can continue your holiday shopping.

ChristmasFest at Old Salem

Date(s): Dec. 14 | 10 a.m.–5 p.m.

Location: Archie Davis Center in Old Salem

Put on by the Moravian Music Foundation & Moravian Archives, this will be a fun-filled event for the entire family. In addition to an arts and crafts vendor fair, there will be food vendors, activities for kids, and even musical performances. You’ll hear Christmas carols as well as other holiday music by a variety of different choirs, bands, brass ensembles, and more. ChristmasFest is modeled after the famous German Christmas Markets and offers an opportunity to experience German and Moravian Christmas traditions.

Looking for more holiday markets and shopping events in Winston-Salem? Our online Events Calendar has a full slate of holiday happenings for you to explore. For an overview of the city’s shopping scene, check out our Insider’s Guide to Shopping in Winston-Salem.