The Graylyn Estate
1900 Reynolda Road, Winston-Salem, NC 27106
Wedding day anchor.
The ceremony and celebration will take place at The Graylyn Estate. Save this one for arrival, parking, and wedding-day directions. In 2026, it was named the No. 1 Best Boutique Hotel in the United States by USA TODAY 10Best readers.
Kimpton Cardinal Hotel
51 East Fourth Street, Winston-Salem, NC 27101
Official wedding weekend hotel.
A polished downtown stay inside the historic R.J. Reynolds Building. The discounted wedding room block is now closed, but guests are still welcome to book the Kimpton directly at its current public rates; booking details are on the Travel page.
The Katharine Brasserie & Bar
401 North Main Street, Winston-Salem, NC 27101
Elegant Kimpton-adjacent dining.
A refined French brasserie and bar in the heart of downtown, especially convenient for guests staying at the Kimpton Cardinal.
Rooster's Wood-fired Kitchen
380 Knollwood Street, Winston-Salem, NC 27103
Polished Southern wood-fired cooking.
A strong option for guests from out of state who want Southern food in a refined setting, with wood-fired dishes, thoughtful ingredients, and a comfortable dining room.
Mozelle's Fresh Southern Bistro
878 West Fourth Street, Winston-Salem, NC 27101
A modern Southern bistro in West End.
A locally owned Southern bistro known for fresh regional ingredients, a cozy setting, and Winston-Salem staples like tomato pie, shrimp and grits, and fried chicken.
The Trophy Room
517 North Liberty Street, Winston-Salem, NC 27101
An elevated bourbon and cocktail bar downtown.
A polished late-night option for guests who want a more refined drink after the wedding, with a speakeasy-style feel and a strong bourbon and cocktail program.
ROAR
633 North Liberty Street, Winston-Salem, NC 27101
A lively downtown stop for drinks and groups.
A fun group-friendly option if guests want to keep the night going after the wedding, with drinks plus games and entertainment in one downtown spot.
Dive Bar Winston-Salem
1131 Burke Street, Winston-Salem, NC 27101
Arcade bar energy on Burke Street.
A casual late-night option with billiards, darts, arcade games, and a livelier post-wedding feel for guests who want something less formal.
The Observatory
701 Trade Street NW, Winston-Salem, NC 27101
Space-themed cocktails in the Arts District.
A newer cocktail bar with a darker, more atmospheric feel, creative drinks, and enough energy for guests who want to keep the night going downtown.
Bar NOLA
1151 Canal Drive, Suite 205, Winston-Salem, NC 27101
New Orleans-style drinks and a large deck.
A New Orleans-inspired bar and event space near West End Mill Works with indoor seating, a large deck, games, and a more casual group-friendly feel.
Camino Bakery
310-B West Fourth Street, Winston-Salem, NC 27101
Coffee and breakfast downtown.
A locally loved bakery and coffeehouse downtown with pastries, coffee, sandwiches, and a practical morning-after stop.
Bobby Boy Bakeshop
1100 Reynolda Road, Winston-Salem, NC 27104
Bakery near the venue side of town.
An artisanal bakeshop and coffee stop near the Reynolda and Graylyn side of town, ideal for pastries, bread, and a slower morning.
Raffaldini Vineyards & Winery
450 Groce Road, Ronda, NC 28670
Where we got engaged.
A Tuscan-style winery in the Blue Ridge foothills with sweeping views and a relaxed, romantic atmosphere.
Reynolda Gardens
100 Reynolda Village Way, Winston-Salem, NC 27106
A quiet escape near the estate.
Beautiful formal gardens and walking trails just minutes from the venue, perfect for a peaceful stroll.
Reynolda House Museum of American Art
2250 Reynolda Road, Winston-Salem, NC 27106
Art, history, and estate beauty.
A historic estate and American art museum with preserved interiors, exhibitions, and a setting that feels quietly grand.
Village Tavern
221 Reynolda Village Way, Winston-Salem, NC 27106
Close, easy, and reliable.
A dependable spot in Reynolda Village with a broad menu and an easy, casual feel.
Krankies Coffee
211 East 3rd Street, Winston-Salem, NC 27101
A local morning favorite.
A popular coffee shop with a relaxed, industrial feel, ideal for breakfast or a casual morning.
Bernardin's at Zevely House
901 West 4th Street, Winston-Salem, NC 27101
An intimate evening out.
An upscale dinner option set in a historic home, with attentive service and seasonal New American cuisine.
Ryan's Restaurant
719 Coliseum Drive NW, Winston-Salem, NC 27106
A classic steakhouse.
A cozy, tucked-away steakhouse with excellent steaks, seafood, and a strong wine list.
Old Salem Museums & Gardens
900 Old Salem Road, Winston-Salem, NC 27101
A signature Winston-Salem experience.
A preserved Moravian historic district with restored buildings, gardens, demonstrations, and one of the city's most memorable walks.
Mast General Store
516 North Trade Street, Winston-Salem, NC 27101
A nostalgic downtown stop.
A charming general store with outdoor goods, apparel, local finds, gifts, and an old-fashioned candy selection.
Downtown Arts District
Winston-Salem, NC 27101
Murals, galleries, and easy wandering.
A lively stretch of galleries, public art, shops, restaurants, and Trade Street character in the heart of downtown.