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.

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Travel plan

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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.

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Number of days

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Type of trip

Standard trip Budget Family Friendly Romantic Stag do

More travel plans

Winston-Salem Wanderlust: A Three Day Adventure!

Explore the history and culture of Winston-Salem on a limited budget by visiting museums and galleries such as the Reynolda House Museum of American Art and the Southeastern Center for Contemporary Art, which offer free admission. Take a stroll through the lush gardens of the Winston-Salem Arboretum and relax in the natural beauty of the area. For affordable eats, visit the locally owned restaurants, cafes, and food trucks, which offer delicious and budget-friendly fare.

Winston-Salem Adventures: Art, History, and BBQ Delights

Winston-Salem is a delightful city in North Carolina that offers plenty of family-friendly activities and attractions. Families can explore the interactive exhibits at the Children's Museum of Winston-Salem, wander through beautiful gardens at the Reynolda House Museum of American Art, and enjoy the thrilling rides at the Adventure Landing amusement park. With its vibrant arts scene, delicious local cuisine, and charming Southern hospitality, Winston-Salem is the perfect destination for a memorable family trip.

Winston-Salem Wanderlust: 5 Days on a Budget

Winston-Salem is a charming destination in North Carolina that offers a variety of affordable activities for budget-conscious travelers. From exploring historic sites like Old Salem and Reynolda House Museum of American Art to hiking in the nearby Blue Ridge Mountains, there's no shortage of things to do. For budget-friendly accommodations, consider booking a stay at a local hostel or budget hotel, and don't forget to indulge in some classic Southern cuisine at local restaurants like Sweet Potatoes and Mozelle's.

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

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.