Winston-Salem Travel Guide

On the beautiful grounds of Graylyn Estate

My husband and I visited WINSTON-SALEM, NC recently for the first time, which is hard to believe since we’ve lived in North Carolina for 25 years! I have no idea why it took us so long to visit, but it definitely won’t be our last trip because we had a wonderful time. I am sharing where we stayed and everything we did in this post, so you can reference it if you ever visit the area.

The beautiful resort exterior (Photo courtesy of Graylyn Estate)

Gorgeous staircase inside Graylyn Estate

Our room (211) was a library in the original home and included an antique writing desk and bookshelves. So charming! (Photo courtesy of Graylyn Estate)

WHERE WE STAYED:

We stayed at the most charming resort in Winston-Salem, GRAYLYN ESTATE. Graylyn Estate is a historic home on 55 acres that has been named on of the best boutique hotels in the country by USA Today. It was originally the home of Bowman Gray, former president of RJ Reynolds, in the late 1920s. It is full of furniture, art and decor from all over the world, with a fascinating history.

Each of the 85 rooms is unique with its own special character. Our room (211) was a library in the original home, so it’s full of bookshelves, a desk and beautiful wood paneling.

We enjoyed the resort’s amenities such as fresh butterscotch cookies each day (so yummy!) and a freezer full of unlimited ice cream. There’s also a billiard room, gym, bikes available to ride and outdoor games such as volleyball and badminton. It really was the perfect place for a getaway and we can’t wait to go back. You can find out more at www.graylyn.com.

WHAT WE DID:

Before our trolley tour with Triad Eco Adventures. Love the eyelashes on the lights of the trolley!

TROLLEY TOUR: We took a 2 hour trolley tour with TRIAD ECO ADVENTURES which was a great way to see Old Salem, downtown and other notable spots around the city. They also offer bike and segway tours, which we were originally planning to do, but with the rain we changed to the trolley so we could stay dry. We learned so much about Winston-Salem during the tour and our tour guide David kept us entertained the entire time.

Beautiful property at Jolo Winery

JOLO WINERY AND VINEYARDS: Our visit to Jolo Winery was one of the highlights of our trip. It is located in Pilot Mountain, 30 minutes from downtown Winston-Salem, and the property is absolutely gorgeous. They offer outdoor and indoor seating, with a full service restaurant. We enjoyed a delicious lunch overlooking the vineyards, and everything we tried on the menu was excellent. If you plan to eat there, reservations are required, but you can also show up without a reservation for a glass of wine in the bar area or outside. I enjoyed their Rose’ “Pink” which has won many awards, and my husband loved the “Crimson Creek” which is similar to a Pinot Noir. We loved the wine so much we bought some bottles to take home with us. I cannot recommend Jolo enough and you can find out more at jolovineyards.com.

SHOPPING: There are several areas around town to shop, and we explored West End, Downtown Arts District and Reynolda Village. All of these shopping areas are within 10-15 minutes of each other, which made it easy to visit multiple shops. Here are some of the shops I enjoyed (pictured above from left to right): Monkee’s of the Village (beautiful women’s clothes, shoes and accessories), Just Be (fun clothes, jewelry and accessories), Mast General Store (charming country store with clothing and food items) and Elizabeth’s at Hanes Park (beautiful home decor & furniture).

Overlook at Pilot Mountain

PILOT MOUNTAIN: This is a beautiful North Carolina State Park located just a half hour from downtown. It offers various trails, a new visitors center and an overlook with stunning views. We did not hike while we were there, but next time we plan to hike Pilot Knob Trail (formerly Jomeokee Trail) which is a 0.9 mile loop around the base of the peak.

Some of the original interiors of the Reynolds estate inside Reynolda House

REYNOLDA HOUSE MUSEUM OF MODERN ART: This beautiful home built in 1917 was originally the home of RJ Reynolds. It now houses a wonderful art collection and still has some of the original interiors of the Reynolds estate.

So many beautiful flowers at Reynolda Gardens

REYNOLDA GARDENS: Exploring these beautiful gardens was a highlight of our trip. Even if you don’t visit the Reynolda House Museum next door, it is worth a trip to come stroll around the gardens. If you want to take a nice walk, take the Reynolda Gardens Loop, a 1.7 mile trail that loops around the entire 130-acre estate.

WHERE WE ATE:

YOUNG CARDINAL: This is a breakfast and lunch spot downtown and was recently ranked one of the best brunch spots by Yelp. They have good sized portions and yummy food, pictured in the photo to the far left. (The avocado toast was excellent.) Plan to get there when they open (8am) or shortly after if you don’t want to wait.

MOZELLE’S: This West End restaurant is popular with the locals and is open for lunch and dinner. They are famous for their tomato pie, which I will definitely try if I go back. It is a charming spot with outdoor seating and I highly recommend the edamame hummus appetizer.

BERNARDIN’S: If you are looking for a special night out with wonderful food, Bernardin’s is a great option. It is the area’s only 5 star restaurant and everything we had was absolutely delicious. (Our dinner is pictured in the second photo from the right.) Bernardin’s is located in a charming house in West End and also offers seating in an enclosed sun room with pretty surroundings.

BOBBY BOY BAKE SHOP: We grabbed some yummy deserts and coffee here for an afternoon treat. They have a wonderful selection of baked goods made fresh daily and also serve light lunch items as well. The mini key lime pie (in the second photo from left) was delicious!

DOUGH JOES: Located in Reynolda Village, this is a great spot to grab breakfast, a sweet treat or coffee. They custom make donuts with the toppings you select and we loved the ones we ordered, pictured in the far right photo. (The cinnamon donuts were my favorite.)

Overall, we really enjoyed our trip and I hope this recap is helpful if you decide to visit Winston-Salem in the future. It is a great place for a weekend getaway, and we will definitely be back!

Thank you to Visit Winston-Salem for sponsoring this post. All content, opinions and photos (unless otherwise specified) are my own.