Choosing the right place to stay can set the tone for your entire trip. Here you’ll find options that range from a lively downtown hotel to quiet historic properties. 

The Kimpton Cardinal Hotel offers spacious, luxurious rooms and a walkable location. It’s a great choice if you want to settle in and explore the city at a relaxed pace without needing to drive to restaurants, galleries, and cocktail bars. 

The Graylyn Estate provides a peaceful retreat just minutes from downtown. Set on 55 acres, the historic manor feels tucked away from the city and almost like staying in a European castle without the eight-hour flight. Treat yourself to a Butler Tour and cap the night with dinner at the on-property restaurant. 

Summit Street Inns is the perfect place for a cozy bed-and-breakfast experience inside two restored historic homes within walking distance of downtown. Each room has its own personality, and a complimentary breakfast makes for an unhurried start to the day.

Ease into the day with a coffee in hand and nowhere you need to rush off to. Grab a seat at Camino Bakery, Louie & Honey’s Kitchen, ByGood Coffee, or Bobby Boy Bakeshop and linger over a latte and delicious pastries. For more ideas, check out our Winston-Salem Coffee Guide. You can also find coffee and food vendors set up at the Cobblestone Farmers Market, where you can wander through local goods, produce, and art.

Next, head to one of the city’s scenic spots for a peaceful walk. The Salem Lake Loop Trail offers an easy lakeside stroll, while Old Salem Museum & Gardens is where you can get lost in historic streets. Start at the visitor center to explore the gift shop and purchase a ticket for an immersive experience. Wander from one historical building to the next as you listen to craftspeople and interpreters tell the stories of the Moravians, Black, and Indigenous peoples of this area. Pause to try Moravian cake and tea or have lunch at one of the cafés. 

Reynolda Gardens is another beautiful place to slow down with blooming flowers and walking trails. Don’t miss the welcome center and gift shop, especially if you are a plant lover. From there, it’s an easy stroll to Reynolda Village, a collection of over 25 shops and restaurants where you can grab lunch and browse for home decor, clothing, and more.

When the afternoon rolls around, spend some time recharging at a spa or relaxing with some retail therapy. Focus on your breathing and unwind at the Himalayan Hideaway Salt Cave, where sessions last 45-minutes and promote overall wellbeing. Oasis at the Mill offers a holistic wellness experience through massage & reiki sessions, halo-salt therapy, tea experiences, and more. 

For something a little different, try contrast therapy—infrared sauna paired with cold plunging—at Pure Sweat Studios, which is known for its range of wellness benefits. The Tiny Spa is a great choice if you’re looking for a more traditional spa experience with massage, facials, and other beauty services. 

If shopping is your preferred form of therapy, spend the afternoon browsing some of the city’s favorite local shops. Stops like Kin & Cottage, The Bookhouse, Fiddle & Fig, Boho Depot, Wood & Thread, and Just Be are fun places to wander, while the Downtown Arts District is perfect for popping into galleries and discovering local artists. 

For more shopping inspiration, check out our guides to the Reynolda Road and Stratford Road Shopping Districts.

As the day winds down, settle into a comfortable spot and enjoy a drink. Joyner’s feels like a neighborhood living room with its cozy, intimate atmosphere. Another popular cocktail bar, easytalk, brings a relaxed speakeasy vibe with unique drinks, while Dutch Light is perfect if you want fresh air and sunset views from its lively patio. Right beside Dutch Light, you’ll find Dram & Draught, a popular neighborhood bar offering craft beer and wine in addition to their cocktails. 

Winston-Salem is the gateway to the Yadkin Valley, and there are over 40 wineries on our doorstep. Childress Vineyards is a high-energy spot with ties to NASCAR, a beautiful patio, and an excellent bistro. Reservations are recommended on weekdays and required on weekends. JOLO Winery & Vineyards offers stunning views of Pilot Mountain and plenty of outdoor seating. Reservations are required for wine tastings and dining at End Posts Restaurant. 

Shelton Vineyards, one of the region's original wineries, has a more laid-back atmosphere, with a patio that often features live music on Saturdays. For an Italian experience, Raffaldini Vineyards is the perfect choice, with a tasting room that transports you to Tuscany and distant mountain views.

Spend your evening enjoying a meal at one of our popular dining spots, then head out for live music. Spring House Restaurant, Bernardin’s Restaurant, and Mozelle’s Fresh Southern Bistro all offer an upscale dining experience with patio seating. Village Tavern and Fourth Street Filling Station are both local favorites for elevated casual dining and also have patios. If you’re craving breakfast for dinner or classic comfort food, don’t miss Midtown Cafe & Dessertery or Mama Zoe’s. 

There are plenty of relaxed venues around the city where you can keep the night going with a drink and live music. Wise Man Brewing and Foothills Brewpub often host performances, Muddy Creek Listening Room offers an intimate space for acoustic shows, and CoalPit Live brings outdoor concerts to the Innovation Quarter when the weather warms up. Rain or shine, The Ramkat features a regular slate of concerts with everything from small indie bands to major household names.

Looking to support the arts during your trip? Head to the downtown Arts District to tour galleries and shops check for local performances in our events calendar. Serenade your senses with performances by the Winston-Salem Symphony, engage your inner thespian with a performance by the Camel City Playhouse, or keep it low key by stopping for an evening movie at a/perture cinema.