Winston-Salem has never entirely left its eighteenth-century Moravian past behind. In fact, Old Salem’s 1766 historic village is actually just a stone’s throw from downtown’s Village Juice Company, which couldn’t be more Instagram-worthy. The juxtaposition of the two old cities (Winston and Salem) and the innovative spirit that combines them into modern day Winston-Salem, is a fascinating study of how cities stay true to their roots, while moving forward through the decades. 

The Moravians, the Eastern European religious sect who settled Old Salem, valued education and innovation and were also expert potters, traders, tanners, and cloth and furniture makers. Their legacy lives on with the impeccably preserved experience designated as the National Historic Landmark District of Old Salem. Stroll along numerous cobblestone streets bordering the grassy town square, and wander in and out of the restored in situ brick-and-timber structures. Here, restored schools, churches, and shops feature authentic eighteenth- and nineteenth-century costumed workers showcasing traditional skills such as baking, gardening, weaving, quilting, and making medicines.

After the Civil War, the city of Winston grew as a thriving industrial center, and both cities joined forces to become a textile and tobacco powerhouse. Roaring through the twenties, Winston-Salem became the biggest and most bustling city between Atlanta and Washington, DC. 

Tobacco magnate R.J. Reynolds built his towering Art Deco monument to the mighty leaf by hiring New York City architects Shreve & Lamb, who went on to use the 1929 skyscraper as an inspiration for their legendary Empire State Building. The gilded lobby ceiling, imported marble floor, and highly polished nickel and brass bas relief elevator doors continue to gleam in its new incarnation, reborn as the elegant Kimpton Cardinal Hotel.

To access downtown Winston-Salem’s architectural gems, don’t miss booking the two-hour, informative, and easy electric bike tour by Triad ECO Adventures. With frequent stops for up-close looks, the tour sheds light on numerous design styles, including The Loewy Building with its geometric motifs and sleek ’50s update, the former post office featuring Beaux Arts details and Corinthian columns, and the First Baptist Church in the Roman Neoclassical style. Additionally, there’s the Winston Tower built in the International Style of the ’60s, and Cesar Pelli’s Wells Fargo building, which is the only postmodern granite-domed skyscraper in the world.

The boutique Hotel Indigo recently opened in the refurbished Art Deco Pepper Building, once a department store from a bygone era. Midcentury modern décor permeates the bar, lobby, and all the guest rooms. They’ve even nodded to the old Sir Winston cafeteria that used to operate in the store’s basement. Renamed the Sir Winston Wine Loft and Restaurant, it’s a stylish spot to imbibe their signature Moravian Mule; look toward the ceiling for clever quotes and original light fixtures, both uncovered during the building’s refurbishment. 

A quick drive from downtown are two Winston-Salem musts, the palatial estates Reynolda and Graylyn, both founded on fortunes made from tobacco and open for touring. Completed in 1932, the 55-acre Graylyn Estate is the second-largest private residence in North Carolina, right behind the Biltmore. Mrs. Bowman Gray, the creative mastermind, was an inveterate shopper, shipping original seventeenth-century paneled walls from Paris and Syria and a marble fireplace from England—even traveling throughout Europe with her husband and a set of her home’s blueprints to make sure everything would fit. She ignored those who looked askance at her eclectic room-by-room décor, which features several design influences: Norman Revival, French Baroque and French Country, English (both Adams and Georgian), Middle Eastern, Italian Renaissance, and Art Deco.

Reynolda, the R.J. Reynolds country manor encompassing 180 acres, offers up a conservatory, formal gardens, and an on-site museum, The Reynolda House Museum of American Art. In addition to the astonishing collection of art, the 33,000-square-foot historic property contains the original 1917 interiors. Both Graylyn and Reynolda are now integral parts of Wake Forest University.

Winston-Salem also features quite a few woman-owned restaurants, perhaps as a result of the original settlers. The Moravians prided themselves on educating and encouraging women as far back as the eighteenth century, even founding Salem College, the country’s oldest operating women’s college. Standouts are the Spring House Restaurant Kitchen & Bar, situated in the last remaining historic mansion on the former Millionaire’s Row, Mozelle’s Fresh Southern Bistro in the funky West End, and Alma Mexicana, in the Bailey Power Plant, a mixed-use development in the revitalized Wake Forest Innovation Quarter.

As the ultimate statement of the past adapting to the present, there are repurposed vintage cigarette vending machines all over town, now called Art-o-Mats. In their new life, they’ve given up smokes and now dispense unique, adorable miniature works of art done by Winston-Salem’s local artists.

With a dash of the funkiness of Asheville, a touch of classic Colonial Williamsburg, and a trendy food scene, Winston-Salem is moving into the future as a town worthy of its moniker, The City of Arts and Innovation.


Graylyn Estate Historic grand estate with Old World flair. The Mews is a private French Normandy-style collection of rooms, and one of four places to stay on the premises. 

Hotel Indigo Midcentury modern interior inside an Art Deco historic building, with a creative cocktail program at the Sir Winston Wine Loft and Restaurant.

The Kimpton Cardinal Hotel Luxury, charm, and distinctive Art Deco details, in a central location with a chef who worked alongside Eric Ripert. The Katherine Brasserie & Bar features seasonal French brasserie cuisine. 


Alma Mexicana The environment is as bright as the authentic flavors in this lively cantina and bar, which also offers outdoor patio dining.

Mozelle’s Fresh Southern Bistro Classic favorites are spun with unexpected updates in this Winston-Salem favorite. 

Spring House Restaurant Kitchen & Bar Dine in this sophisticated 1920s Southern mansion, reborn as an award-winning New American eatery.


Bike Tour with Triad ECO Adventures Segway, electric bike and trolley tours with private, well-informed guides.

The Chair Library at Salem College See, sketch, photograph, and touch 45 iconic original chairs designed by international designers and architects including Charles Rennie Mackintosh, Marcel Breuer, Frank Gehry, Philippe Starck and Eileen Gray. 

Old Salem Museums and Gardens Tour the original Moravian settlement and gardens by wandering in and out of the historic buildings, plus visit the decorative arts museum. Pop into the bakery to buy traditional treats. Great for kids.


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