3-Day Arts, Food & History Trip to Winston-Salem

Explore history, art, and love in Winston-Salem.

22 April 2023

Discover the charm and history of Winston-Salem on a romantic getaway. Stroll through the gardens of Reynolda Village and share a romantic meal at one of the city's renowned restaurants. Enjoy a stay in a luxurious hotel and take in the beauty of this southern gem.

Save and get deals

Travel plan

Getting latest place information
Day 1

Discovering the Arts

  • Stay at Kimpton Cardinal Hotel, a luxurious hotel with a rooftop bar giving views of the city. Start your trip by exploring the arts in Winston-Salem:
  • Visit the Reynolda House Museum of American Art to see the works of famous artists like Georgia O'Keeffe.
  • Admire the colorful street art murals in the downtown area.
  • Take a stroll through the gorgeous gardens of the Wake Forest University campus, which also holds an impressive collection of art and artifacts.
  • Check out the unique, indie theaters like The Ramkat and The Olio to see live performances.
Day 2

Tasting Winston-Salem

  • Get ready for a day filled with delicious culinary experiences in Winston-Salem:
  • Have breakfast at The Tavern in Old Salem, renowned for their Moravian chicken pie and homemade biscuits.
  • Take a winery tour and tasting at the sprawling Childress Vineyards.
  • Eat lunch at Krankies Coffee, a popular lunch spot that serves artisanal dishes and charcuterie boards.
  • Have a romantic dinner at The Katharine Brasserie and Bar, an upscale restaurant located in a restored Art Deco building.
Day 3

History & Adventure

  • Explore the rich history and adventurous side of Winston-Salem on your final day:
  • Visit Old Salem, a historic Moravian settlement complete with cobblestone streets and colonial-era buildings.
  • Take a hike at Pilot Mountain State Park, which has challenging trails but rewards you with breathtaking views of the surrounding mountains.
  • Take a Winston-Salem Segway tour to see more of downtown, stopping at landmarks like the Winston-Salem First National Bank and the Fourth Street Fountain.
  • End the day with a visit to The Porch, a local speakeasy that serves creative cocktails and has a live jazz band.

Length of stay

1 day 2 days 3 days 4 days 5 days

Type of trip

Standard trip Budget Family Friendly Romantic Stag do

How to get there

Plane

The easiest way to get to Winston-Salem by air is to fly into Piedmont Triad International Airport (GSO) located approximately 30 minutes outside of the city. Major airlines such as American, Delta, and United fly into GSO from various destinations across the United States.

Car

Driving is also a popular way to get to Winston-Salem. If you're coming from the north or south, simply take Interstate 77 to Interstate 40 West. If you're coming from the east or west, take Interstate 40 to Winston-Salem. Parking can be found in various locations throughout the city, including parking garages and street parking.

Train

While there is no direct train service to Winston-Salem, you can take Amtrak to the nearby city of Greensboro, located approximately 30 minutes away. From Greensboro, you can then take a Greyhound bus or rent a car to complete your journey to Winston-Salem.

Boat

There is no direct water transportation to Winston-Salem as it is not located on a major body of water. However, if you have a boat, you can potentially access the city via the Yadkin River or nearby lakes such as High Rock Lake or Belews Lake, which are all within driving distance of Winston-Salem.

Bus

Greyhound offers bus service to Winston-Salem from various locations across the United States, including nearby cities such as Greensboro and Charlotte. The Greyhound bus station is located in downtown Winston-Salem, making it a convenient option for those staying in the city center.

Destination

Winston-Salem

Winston-Salem, the city that sounds like the lovechild of a British prime minister and a tobacco plant. But don't let the name fool you, there's more to this place than just smoke and politics.

 Save and get deals

Number of days

1 2 3 4 5

Type of trip

Standard trip Budget Family Friendly Romantic Stag do

More travel plans

5-Day Family Fun in Winston-Salem: Budget-Friendly Bliss

Winston-Salem, located in North Carolina, offers a delightful family-friendly trip with a perfect blend of culture and outdoor activities. Take a trip to the Reynolda House Museum of American Art, where kids can explore the beautiful gardens and learn about American art. Don't miss a visit to the SciWorks Science Center, offering interactive exhibits and hands-on learning experiences that will keep the whole family engaged and entertained.

5-Day Romantic Getaway in Winston-Salem

Located in North Carolina, Winston-Salem offers a charming destination for couples looking for a romantic getaway. Discover the city's rich history through a visit to the restored Old Salem Museum & Gardens. Savor the area's vibrant cuisine and world-class wines at local restaurants and wineries.

Get Romantic in Winston-Salem: A 4-Day Adventure

A romantic trip to Winston-Salem, United States takes couples on a journey through picturesque landscapes and charming neighborhoods. Explore the art galleries, vintage shops, and cafes along the cobblestone streets, as well as the historic sites that showcase the city's rich cultural heritage. Dine on delectable Southern cuisine and sample locally produced wines, all while basking in the city's serene ambiance.

Weekend Romance in Winston-Salem

Winston-Salem, known as the "City of Arts and Innovation" offers a great getaway for couples seeking a romantic trip. Stroll hand in hand through the historic Old Salem district, catch a performance at the Winston-Salem Symphony or hike the trails at Pilot Mountain State Park for panoramic views. Don't forget to end the night with a glass of wine at one of the many local wineries.