Day Date Ideas We're Swooning Over

Winston-Salem's hip and historic culture provides an endless amount of date ideas, whether it's your first date or your thousandth. From sprawling lawns and garden terraces to charming courtyards and museum backdrops, we've selected several locations to plan your next day date in Winston-Salem before enjoying your night out on the town.

Planning a wedding or other romantic celebration in the near future? Each of these stops pulls double duty as wedding venues with some serious wow factor. For a full list of venues unique to Winston-Salem including vineyards, museums, and boutique hotels, visit our wedding page.

Winston-Salem's hip and historic culture provides an endless amount of date ideas, whether it's your first date or your thousandth. From sprawling lawns and garden terraces to charming courtyards and museum backdrops, we've selected several locations to plan your next day date in Winston-Salem before enjoying your night out on the town.

Planning a wedding or other romantic celebration in the near future? Each of these stops pulls double duty as wedding venues with some serious wow factor. For a full list of venues unique to Winston-Salem including vineyards, museums, and boutique hotels, visit our wedding page.

Tour & Explore the Historic Graylyn Estate

A quarter-mile stretch of maple-canopied road leads up to the historic Graylyn Estate. Nestled on 55 sprawling acres, this 1932 Norman Revival-style manor house, and now an 85-room hotel, invites its guests to be "Lord or Lady of the Manor." Just in time for Valentine's Day, you and your honey can book a lavish stay with their "Romance Getaway Package," inclusive of complimentary Champagne, chocolate-covered strawberries, and roses. Or, just spend the day touring the historic architecture and learning the history of the Gray family while on a private butler tour.* Be sure to make dinner reservations for later that evening. Graylyn offers an outstanding dining program led by executive chef, Gregory Rollins.

Discover Downtown's Historic Brookstown Neighborhood

Stretching from downtown's Historic West End to the Historic Salem district, Brookstown Avenue is a burgeoning neighborhood where a former tobacco mill houses a charming Inn historic train depot is now home to a local bistro. Planning your Valentine's Day date in the Brookstown corridor is sure to provide memories to cherish for years to come. We recommend:

Starting the day with baked-from-scratch baked goods at Camino Bakery and locally roasted coffee from ByGood Coffee
Then take a stroll through Historic Old Salem where a portion of the area's founding Moravian community settled in 1766. Here find the state's oldest standing African American church, the oldest operating women's college in the country, beautiful heirloom gardens, and the serene God's Acre cemetery -- plus so much more.
Stop in for lunch at Willow's Bistro, located inside a historic train depot. Executive chef Nikki Farrington dishes out daily specials including scallops, hummus, and flatbreads. Ate one too many scallops? Walk it off with a stroll on the Salem greenway that runs directly alongside the restaurant.

Overnight at The Historic Brookstown Inn. Located inside an 1837 cotton mill, the Brookstown Inn Hotel features much of the original architecture with exposed brick and wood ceiling beams as design highlights. Their "Romantic Getaway Package" includes a bouquet of seasonal flowers by local florist and champagne on ice waiting for you in your room. (P.S. - be sure to say hello to the resident cat, Sally.)

Stroll Our Heirloom Gardens Collection

Wake up your planting plans--and your creative side--with a tour through Winston-Salem's collection of historic and heirloom gardens. Our lush gardens date back more than 250 years and offer a peek into our colorful past. Some would say that our gardens are a study of horticulture and history. While there is no right or wrong starting point, feel free to navigate them in chronological order as we've suggested here. To read our full gardening guide with details on each, click here.

Southeastern Center for Contemporary Art (SECCA)

Now home to the Southeastern Center for Contemporary Art (SECCA), the 1930s estate of textile industrialist James G. Hanes presents a natural backdrop of a boxwood garden, wisteria trees, and an expansive lawn leading to the manmade lake. Start indoors and explore the rotating exhibitions (free admission!) then head outside to meander the grounds or set up a picnic on the lawn - easy to do with food ordered from one of several nearby eateries.

Enjoy the Great Outdoors at Tanglewood Park

A love story in and of itself, Tanglewood Park was purchased by William Neil Reynolds (brother to R.J. Reynolds), and his wife Kate, in 1921. On the grounds of the historic Manor House Bed & Breakfast, William had a rose garden planted for his beloved wife. Visit the 5.5-acre arboretum, now home to more than 20 gardens with 75-100 different varieties of plants blooming at any given time. Book a romantic horseback ride through the park trails or tee off for a friendly competition in a round of golf on one of the park's award-winning courses.

Hit a Strike (or A Hole in One) at ROAR

Winston-Salem's downtown scene is lively and vibrant, with endless options for entertainment. One of the newest options is ROAR, located in the downtown arts district. Boasting multiple entertainment and dining spaces, you can choose your adventure from their chic boutique bowling alley, virtual golf simulator, food hall and self-serve beer wall, exclusive rooftop bar, and even indoor blacklight putt-putt! If you're looking to impress your date with all the fun you can imagine under one roof, ROAR is the place for you. Make it a group date and rent a private dining space or rooftop cabana!