3 Days in Winston-Salem: Itinerary for the Perfect Long Weekend in Winston-Salem, North Carolina

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Thinking about a Winston-Salem weekend getaway and wondering what to do during your trip?

North Carolina - Winston Salem - Reynolda Gardens - Jordan and Stehpanie

Well, the perfect long weekend in Winston-Salem is easier to accomplish than you might think!

This Winston-Salem itinerary is designed for you to see the best of Winston-Salem in three days, but there are also tips for what to do if you only have one or two days in Winston-Salem or if you have four days.

Read next: 17 Winston-Salem Travel Tips: Guide to Planning a Trip to Winston-Salem, North Carolina!

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3 Days in Winston-Salem Itinerary for the Perfect Long Weekend in Winston-Salem, North Carolina

Good to Know: We were guests of Visit Winston-Salem during our Big Southern USA Road Trip. As always, all opinions are my own.

In this Article:

Essential Travel Resources for 2022

These are my favorite companies that I use on my travels.

Find cheap flights with CheapOair.

Find the best deals on hotels & vacation rentals on Booking.com or Hotels Combined.

For road trips and ground transportation, rent a car through Discover Cars or RentalCars.com.

For RV rentals and camper vans, book through RVshare.

Find the best city tours, day tours, bus tours, & skip-the-line tickets on GetYourGuide, Viator, and Big Bus Tours.

Find local food tours, cooking classes, and exclusive dining experiences on Eatwith.

Find information and cruise reviews on Cruise Critic.

For packing and travel essentials order via Amazon.

For travel guidebooks to have with you during your trip, I always pick one or two (or five) from Rick Steves, Lonely Planet, Moon Travel Guides, or Fodor’s Travel Guides.

Get reliable travel insurance through World Nomads.

Store your luggage safely with Radical Storage.

Book an affordable family or romantic photography session on your trip through Flytographer (Use the code HISTORYFANGIRL for 10% off your first photoshoot).

The Top 5 Most Popular Winston-Salem Tours & Attractions

Before you dig into all the city has to offer, you should know that these are the most popular guided tour and attractions in Winston-Salem.

Winston-Salem Historical Ghost Tour

Bethabara Historic Park Tour

Old Salem Museums and Gardens Tour

Reynolda House Tour

Twin City Trolley Tour

Where to Stay in Winston-Salem

If you’re looking to stay in one of the best hotels in Winston-Salem, then check into the three-star Historic Brookstown Inn.

North Carolina - Winston Salem - The Historic Brookstown Inn - Dining Room

This is where we stayed while we were here, and it was lovely. 

Our room was spacious, with a separate living area (great for traveling with a toddler!), the included breakfast and evening cookies were delicious and a great way to start and end our days, and the location was great for seeing the city’s historic sites.

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North Carolina - Winston Salem - The Historic Brookstown Inn

The inn touts itself as “A living museum of History, Art & Treasure in Winston-Salem, NC,” and it feels that way.

The building itself is an old mill that has been preserved, and the architecture of the building and grounds is unlike any place I’ve stayed before.

Historic objects are lining the halls, the furniture and decor of the rooms lean historic with modern comforts, and the large center courtyard reminds you that this isn’t your typical hotel.

North Carolina - Winston Salem - The Historic Brookstown Inn

From check-in to check-out, I felt peaceful and easy whenever we were at the Inn, which is exactly how you want to feel on a weekend retreat from your typical busy life.

Book your stay at the Historic Brookstown Inn.

If you are looking for a four-star hotel in Winston-Salem, then opt for the Kimpton Cardinal Hotel.

North Carolina - Winston Salem - Innovation Quarter - Bailey Park in Winston Salem - Art Deco Building

Located in downtown Winston-Salem in the historic R.J. Reynolds building, this is a luxury hotel complete with a spa, a French restaurant, and a bowling alley on-site.

Book your stay at the Kimpton Cardinal Hotel.

If you would like to stay out near Reynolda, the Graylyn Estate is located nearby in a beautiful green setting.

Good to Know: Book your Winston-Salem accommodations early!

Because this is a university city, you never know when a game or graduation will make your preferred dates sell out. 

A good rule of thumb is to always book your room early if you will be going to an American college town or city for your trip.

We encountered room shortages on our road trip in both Winston-Salem (Wake Forest University) and in Knoxville (where the University of Tennesee is located).

When I travel in the US, I use Booking.com since I can easily find rooms with free cancellation. 

This means I can book hotels early and cancel if we move the trip dates or decide not to go.

See all Winston-Salem Accomodations on Booking.com

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17 Winston-Salem Travel Tips: Guide to Planning a Trip to Winston-Salem, North Carolina!

How to Get to Winston-Salem

There are several ways to get to Winston-Salem from various parts of the US.

Flying to Winston-Salem

When I fly to North Carolina, I usually fly into Charlotte Douglas International Airport, which is an international hub and easily accessed from most of North America.

North Carolina - Charlotte - Airport
A very grainy view of the Charlotte skyline while landing at Charlotte Douglas

However, the closest airport to Winston-Salem is the Piedmont Triad International Airport in Greensboro.

There’s also the Smith Reynolds Airport, which is just a few minutes outside of the city, but that’s mostly for people flying private.

If you’re flying to Winston-Salem, I would check flights at both Charlotte and Piedmont airports and compare the prices.

If you fly into Piedmont International, the drive to Winston-Salem is about thirty minutes, while it’s about an hour and fifteen minutes for Charlotte Douglas.

If you need your ground transportation and want to rent a car, you can reserve one in advance for pickup at either airport.

I use Discover Cars when I travel to help save money on car rentals, which have gotten quite pricey lately!

Reserve your rental car for your trip to Winston-Salem.

Other ground transportation options include taxis and rideshare companies like Uber and Lyft.

Driving to Winston-Salem

This is the most common way to arrive in Winston-Salem. Located on I-40, Winston-Salem is easy to drive to from many major cities in the Southeast. 

North Carolina - Winston Salem - Jordan in the Car Seat

In my Winston-Salem travel tips, I list the drive time from most of the major cities in the region.

If you don’t want to drive your own car, you can get a rental car in your home city and drive it round-trip.

Taking the Bus to Winston-Salem

You can use Greyhound to take a bus to Winston-Salem. I have taken Greyhound on multiple trips in the US (but not to Winston-Salem).

Greyhound is reliable up to a point. I’ve found the actual travel times can vary tremendously from what was listed on my ticket.

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North Carolina - Winston Salem - Bus Station

This becomes more of a problem the more stops and transfers are included on the route.

I only use Greyhound when I have no other option because they usually take longer than driving and it usually costs the same or more than I would spend on gas anyways.

Unlike Europe or Asia where taking the bus is usually the most cost-effective way to get around, in the US it’s usually more expensive than driving while taking longer.

Taking the Train to Winston-Salem

Theoretically, it’s possible to take the train to Winston-Salem via Amtrak, though the city is not on a major route. 

To see if your route is available on Amtrak for your Winston-Salem getaway, check the Amtrak website.

How to Get Around Winston-Salem

If you want to see most of the best sites in the city, you will want to have a car during your visit to Winston-Salem.

This is because some of the best sites, like Old Salem and Reynolda, aren’t within walking distance of downtown. 

North Carolina - Winston Salem - Valentine and Jordan - Downtown Winston-Salem is walkable but you'll want a car (or rideshare) to get to places like Reynolda, Old Salem, and Bethabara
Downtown Winston-Salem is walkable but you’ll want a car (or rideshare) to get to places like Reynolda, Old Salem, and Bethabara

However, there are rideshare options and city buses available for those who prefer not to have a car available and still want to see the sites on the outskirts of town.

Both Uber and Lyft operate in Winston-Salem if you want to use a rideshare company.

Check out the Winston-Salem Transit Authority’s website for bus routes.

You can also ask your accommodations for reliable taxi recommendations.

Otherwise, if you aren’t driving to the city on a road trip, you can rent a car for your trip.

Reserve your rental car for your trip to Winston-Salem.

The Perfect 3 Day Weekend in Winston-Salem, North Carolina

Get ready to have an amazing Winston-Salem weekend!

Good to Know: Not everything listed on this itinerary is open year-round or daily even during peak seasons. 

You should use this as a general travel guide and then check with the activities and restaurants to ensure they are open during your exact trip dates.

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I recommend booking activities and tours ahead of time to avoid sold-out tours. I don’t usually make reservations for restaurants, but when I do I use Open Table.

Winston-Salem Day 1: Old Salem Museums & Gardens + Downtown Arts District

Winston-Salem is synonymous with Moravian culture, and you’ll spend your morning learning (and tasting) this unique history in Old Salem.

During the afternoon, you’ll get to enjoy the local art scene in the Downtown Arts District before enjoying a dinner of Carolina BBQ.

Breakfast: Start Your Day at Your Accommodations or Grab a Krispy Kreme Donut

Our hotel served a wonderful breakfast, and if yours does then I would suggest enjoying it on your first morning.

However, if it doesn’t, head to the closest Krispy Kreme! These delicious donuts have taken America by storm, but they started right here in Winston-Salem!

If you want to be true to the original, which is no longer standing (unfortunately), grab a few glazed donuts (the original offering) and head to the plaque that commemorates where they were first sold.

Krispy Kreme Address: 259 S Stratford Rd, Winston-Salem, NC 27103

Plaque Address: 534 South Main St. Winston-Salem, NC 27101

Morning: Wander through Old Salem Museums & Gardens

I hope you fueled up because this morning you start your Winston-Salem vacation with a bang!

North Carolina - Winston Salem - Old Salem Museums and Gardens - Single Brother's House

Perhaps the most famous thing to do in the city is visit Old Salem. 

This is a living history park – think Colonial Williamsburg but way less touristy. 

There are shops, museums, delicious dishes, historic houses, and gardens to see, so wear your comfortable shoes!

About Old Salem

Exploring the Old Salem Historic District will get you up close and personal with Salem, one-half of the Twin City of Winston-Salem (Salem and Winston were officially incorporated as one city in 1913).

North Carolina - Winston Salem - Old Salem Tavern

Old Salem is the oldest part of the city. Moravian settlers came to the area in 1753. They founded the town of Bethabara (more on that on day 3!), and in 1766 they began construction on the town of Salem.

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Despite it being the third Moravian settlement in the area, it was in the original plan for Salem to be the main town for the Moravian community. 

North Carolina - Winston Salem - Old Salem Museums and Gardens

Moravians were a religious sect who were named for the region of Moravia in the modern-day Czech Republic. 

By the time they came to North Carolina, they had already founded other settlements in the United States. Their first attempt was a failed settlement in Savannah, Georgia. 

They also founded the much more successful Bethlehem, Pennsylvania.

Today there are still practicing Moravians in the USA, with thirteen states having active Moravian congregations.

North Carolina - Winston Salem - Old Salem Museums and Gardens - Stephanie
Things To Do in Old Salem

There’s a lot to do here, so how long you choose to spend here is dependant on how much you love historic gardens, shops, taverns, and houses. 

I mean, I could spend all three days in Winston-Salem just exploring Old Salem, but for the sake of this itinerary, you should prepare to spend a minimum of four hours here, but expect it to be more if you love history and museums!

North Carolina - Winston Salem - Old Salem Museums and Gardens - Valentine and Jordan

Pro Tip: If you don’t want to do self-guided tours and visit buildings on your own, you can pre-arrange a guided tour.

Good to Know: Some areas are only open Wednesday through Saturday from 10:00 am – 2:00 pm, while other areas are open to the public at all times.

There’s no gate or entry fee to walk on the streets, so if you can’t fit your trip into a day that the museums are open, there are still fun things to do.

Check Old Salem’s website for current hours before leaving on your trip.

Visitors Center

If you plan on going inside the buildings as well as visiting MESDA (below), start with a stop in the Old Salem Visitor’s Center.

This is where you can pick up tickets to be able to go inside the historic buildings as well as the self-guided MESDA galleries.

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Tickets are good for two days, so if you find you want to come back and see more, you will be able to.

Address: 900 Old Salem Road, Winston-Salem, NC 27101

Museum of Early Southern Decorative Arts (MESDA)
North Carolina - Winston Salem - Old Salem - Frank L. Hornton Museum Center MESDA

A must-visit, MESDA is the “preeminent center for the research and study of Southern decorative arts and material culture.”

In this art and history museum, you can learn about the communities of early Carolina through artwork as well as local crafts. 

Its mission is to share the “diverse cultural history of the early South—with special emphasis on the Moravians in North Carolina, enslaved and free people of African descent, and indigenous peoples of the Southern Woodlands.”

You can visit the self-guided galleries on your own or arrange a guided Two-Hour Connoisseur Tour.

Address: 924 South Main Street, Winston-Salem, NC 27101

Winkler Bakery
North Carolina - Winston Salem - Old Salem

Famous for Moravian Cookies and Sugar Cake, this bakery is a fabulous place to stop by when you get hungry!

The staff dress in period costumes, though the baked goods are made off-site so they don’t run out of goodies quite as quickly.

North Carolina - Winston Salem - Old Salem - Winkler Bakery - Woman Baking

The shop also has some of my favorite Winston-Salem souvenirs, so make sure to stop here if you are looking for gifts to take back to friends and family!

While you’ll have many chances to buy Moravian cookies and other goodies on your trip, I left with twelve tins of ginger cookies from different stores in the city and it wasn’t enough. 

North Carolina - Winston Salem - Old Salem - Winkler Bakery - Sugar Cake

So don’t feel bad if you go a little overboard shopping here!

Address: 900 Old Salem Road, Winston-Salem, NC 27101

Self-Guided Tour of Salem Pathways
North Carolina - Winston Salem - Old Salem Museums and Gardens - Salem Pathways

Free and open 24/7, Salem Pathways allows visitors to follow the lives of different people who lived in Old Salem.

Using your cell phone to scan QR codes, you’ll learn about what life was like in Old Salem for seven different residents spanning over two hundred years!

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Address: Use this map to choose your starting point.

More things to Do in Old Salem

Seed Saving Lab

Boys’ School

Miksch House & Garden

Salem Stitches

Farmers Market

Potter’s Workshop at T. Bagge

Moravian Book & Gift

E.A. Vogler Coffee & Confections

Carpentry in the Miksch Yard

Old Salem Tavern (Currently Closed)

Lunch: Get a Taste of Moravian Pie at Muddy Creek Café & Music Hall

Before you leave Old Salem Museums & Gardens, enjoy lunch at Muddy Creek Cafe. Remember they close for lunch by 2, so make sure to get here early enough to enjoy your Moravian Pie!

Good to Know: The Music Hall side is usually reserved for nights, so you probably won’t run into live music unless you plan on going for dinner.

Address: 137 West Street, Winston-Salem, NC 27101

Afternoon: Be Inspired (and Shop!) in the Downtown Arts District

North Carolina - Winston Salem - Downtown Winston Salem

Winston-Salem’s Downtown Arts District, also known as DADA, is full of great opportunities to enjoy works by local artists as well as crafts and pottery.

North Carolina - Winston Salem - Delurk Gallery

Centered around Trade Street and Liberty Street, the area is one of the best art districts in the US. 

You’ll find great art galleries a-plenty. Some of the most well-known are Delurk Gallery, Piedmont Craftsmen Gallery, and Red Dog Gallery.

North Carolina - Winston Salem - Downtown Winston Salem - Downtown Winston Salem - Downtown Arts District - Red Dog Gallery

Something I love about the galleries in DADA is that many of them have galleries with art that is very affordable. I found pieces I loved that were priced from $25-300 dollars.

This means that even visitors who don’t usually want to spend a lot of money on souvenirs or art can find something they love.

North Carolina - Winston Salem - Downtown Winston Salem - Downtown Winston Salem - Downtown Arts District - Red Dog Gallery

The pieces I picked up at Red Dog Gallery were under $30 each! (Now I just have to get them framed…).

One of the best free things to do in Winston-Salem is located next to Red Dog Gallery, ARTivity on the Green is Winston-Salem’s first art-themed park. 

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North Carolina - Winston Salem - Downtown Winston Salem - Downtown Winston Salem - Downtown Arts District - ARTivity Park

It’s a beautiful space that will spark your imagination. It’s also one of the most beautiful photo spots in Winston-Salem.

Start at Delurk Gallery and spend your time exploring the area’s galleries, green spaces, and murals!

Delurk Address: 207 W 6th St, Winston-Salem, NC 27101

Dinner: Get a Taste of Carolina Barbeque at Camel City BBQ Factory

North Carolina - Winston Salem - Downtown Winston Salem - Downtown Winston Salem - Downtown Arts District - Camel City BBQ Factory

There’s no shortage of great restaurants and great food in Winston-Salem, but you can’t come to North Carolina without indulging in some great Carolina barbeque!

Located near ARTivity, you can saunter on over when you’re shopped out.

Address: 701 N Liberty St, Winston-Salem, NC 27101

Evening: Sip Local Craft Cocktails at Broad Branch Distillery 

Located on Trade Street, this is a great way to end your first day in Winston-Salem.

Unfortunately, the Cocktail Bar is only open on Saturdays from 1-9 PM, so this is only an option if your first full day is on a Saturday.

If you won’t be in town on a Saturday, you can still stop by here to shop and even go on a distillery tour. Check with the distillery ahead of time to arrange a tour.

Otherwise, there are many breweries and bars in the area where you can find a nightcap. Otherwise, head back to your accommodations and get rested for day 2! 

Address: 756 Trade St NW, Winston-Salem, NC 27101

Winston-Salem Day 2: Reynolda, SECCA, + Haunted Winston-Salem

There are so many beautiful green spaces in the Winston-Salem area, but Reynolda has to be seen to be believed.

You’ll spend most of the day at Reynolda enjoying the art, grounds, and food, before heading over to nearby SECCA.

Depending on the timing of your visit, you can end your day learning Winston-Salem ghost stories plus enjoy a lovely dinner in the city’s finest brasserie.

Breakfast: Taste Local Craft Donuts at Dough-Joe’s Doughnuts & Coffee

We will begin with breakfast in Reynolda Village, so get ready to have a packed day of wonderful Winston-Salem activities!

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North Carolina - Winston Salem - Reynolda Village - Dough-Joe's Donuts

On day one in Winston-Salem, we tasted the international donut sensation Krispy Kreme, which got its start right here in Winston-Salem.

For our second day in the city, foodies will love checking out the city’s more modern donuts – lovingly handmade at Dough-Joe’s! 

North Carolina - Winston Salem - The Historic Brookstown Inn - Donut from Dough-Joe’s Doughnuts & Coffee

And each donut is made-to-order, so you can get it exactly how you like it (though you might want to try something new!).

You’ll also find a full coffee bar, iced coffee (my fave), seasonal drink specials like Butterbeer, and an assortment of freshly made pastries and cookies.

North Carolina - Winston Salem - Reynolda Village - Dough-Joe's Donuts - Cookies and Muffins

The interior is cozy and chic, so you can choose to eat inside if you would like, or you can eat on the patio or take your breakfast to go and eat during your walk around Reynolda Village.

North Carolina - Winston Salem - Reynolda Village - Dough-Joe's Donuts - Couches

Make sure not to leave hungry, because you have a lot to do at Reynolda!

Address: C, 114 Reynolda Village, Winston-Salem, NC 27106

Morning: Explore the Reynolda Historic District at Reynolda Village, Reynolda Garden, + Reynolda House Museum of American Art

If this will be your first time in Winston-Salem, you might not be aware of just how big the Reynolds family legacy is here – for better and for worse.

North Carolina - Winston Salem - Reynolda Village - Lantern

Reynolda is one of the best parts of their legacy. The estate of R.J Reynolds and his wife Katharine Smith Reynolds was once a self-sufficient country estate.

There are three main areas of Reynolda: the house, the gardens, and the village. You can choose to visit them all, or you can choose the places that interest you the most.

North Carolina - Winston Salem - Reynolda Village - Reynolda House Gardens & Trail - Waterfall - Stephanie

Spoiler Alert: I love them! I really would try to visit all three, but it depends on your interests and level of mobility whether that will be something you want to do on your trip.

Reynolda Village
North Carolina - Winston Salem - Reynolda Village Boathouse and Wetlands

This is the former land and estate buildings (minus the house). Today there are shops, hiking trails, and even a hidden waterfall. 

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Address: 2201 Reynolda Road Winston-Salem, NC 27106

Reynolda Garden
North Carolina - Winston Salem - Reynolda Gardens

Today the former estate gardens are managed by Wake Forrest University. The entrance is free and you can visit the historic greenhouse, the rose gardens, and weeping cherry trees in a beautiful setting.

Address: 100 Reynolda Village Winston-Salem, NC 27106

Reynolda House Museum of American Art
North Carolina - Winston Salem - Reynolda House Museum of American Art

While the gardens and grounds are open to the public, the main house has been turned into an art museum. 

The collection includes works by many important American artists including Mary Cassatt, Georgia O’Keeffe, and Gilbert Stuart.

North Carolina - Winston Salem - Reynolda House Museum of American Art

The house is also beautiful to see in its own right. Among the beautiful rooms include luxury bedroom suites, a bowling alley, and even a stunning indoor pool!

Tickets are $18 for most adults and admission is free for children under 18.

North Carolina - Winston Salem - Reynolda House Museum of American Art - Swimming Pool

Pro Tip: This is one of the top things to do in the city according to Tripadvisor, so don’t miss it!

Address: 2250 Reynolda Road Winston-Salem, NC 27106

Lunch: Spend a Quiet Lunch in Reynolda Village at May Way Dumplings

A local Winston-Salem favorite, the fabulous May Way Dumplings in Reynolda Village is the perfect way to wrap up your time in this corner of the city.

North Carolina - Winston Salem - Reynolda Village - May Way Dumplings

Famous for Chinese noodles and dumplings, you order at the window and then you can take your food to enjoy at one of the tables outside or anywhere else in the village that your heart desires.

North Carolina - Winston Salem - Reynolda Village - May Way Dumplings

There is a courtyard a little way down the black that is full of tables if you want a little more peace and quiet!

Pro Tip: Do not skip the buns! You can order hot steam pork buns or hot veggie buns (or both!).

Address: 113 Reynolda Village, Winston-Salem, NC 27106

Afternoon: See Art from the ‘New South’ at the Southeastern Center for Contemporary Art

After lunch, you’re just a hop, skip, and a jump away from our afternoon activity – seeing SECCA! 

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North Carolina - Winston Salem - SECCA - Hanes

The Southeastern Center for Contemporary Art is located in the former home of the Hanes family (of Hanes Her Way fame).

However, unlike Reynolda House, this experience is more like visiting a modern art museum that happens to have some rooms in a house versus a grand house tour experience.

North Carolina - Winston Salem - SECCA - Hanes

It’s fun to juxtapose how two extremely wealthy families chose to leave their estates for the public to enjoy in such different ways.

At SECCA, the art is front-and-center. It’s contemporary art by southeastern artists (hence the name).

You’ll find great exhibits thoughtfully curated as well as a gallery of affordable art that you can purchase if you want to take back some as a souvenir from Winston-Salem.

North Carolina - Winston Salem - SECCA - Hanes

​There are also special events here, including live performances, so keep an eye on their calendar.

Good to Know: If you don’t usually do two museums in one day, rest assured that SECCA and Reynolda House are two very different experiences and you need to have both to see what the New South is all about.

Address: 750 Marguerite Dr, Winston-Salem, NC 27106

Dinner: Enjoy Fine Dining at Katharine Brasserie & Bar

​One of the best fusion cuisine mixes I have come across in the US is when a great chef mixes French dishes with traditional Southern food. 

The combination of flavors and dishes is sumptuous and sophisticated, with great seafood options and a large wine selection.

North Carolina - Winston Salem - Innovation Quarter - Bailey Park in Winston Salem - Art Deco Building

Located in the  Kimpton Cardinal Hotel, you can appreciate the art deco interiors of the historic R.J. Reynolds building are a beautiful setting to end your day.

The building itself is an important landmark in the city, as it was the muse for the Empire State Building!

The restaurant is named after Katharine Reynolds, so it is a fitting end to a day spent seeing her estate and learning about her legacy at Reynolda.

Address: 401 N Main St, Winston-Salem, NC 27101

Evening: See Winston-Salem’s Spooky side on a Ghost Tour (Schedule Permitting)

If you happen to be in town on a Tuesday or Saturday, then you’re in luck! There is a fabulous Winston-Salem Historical Ghost Tour of the West End Historic District offered every week throughout the year.

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The tour leaves at 7 PM, so if you can go on the tour, make sure to book it ahead of time and make a dinner reservation for after.

I love going on local ghost tours. You hear fun (and chilling) stories. 

They’re a great way to see a different side of the city, especially if you need fun things to do in Winston-Salem at night!

Book your Winston-Salem Historical Ghost Tour

Winston-Salem Day 3: Bethabara, Shopping, Ice Cream in the Park, + Craft Beer

Breakfast: Enjoy Breakfast or Brunch Downtown

There’s something so lovely about having a nice breakfast downtown in a city that’s not your own.

North Carolina - Charlotte - Brunch at Famous Toastery
Eating brunch at Famous Toastery

A few places that serve breakfast downtown:

Famous Toastery

The Katharine

Six Hundred (Sundays Only)

Other popular spots are the Midtown Cafe & Dessertery (in Midtown) and the Old Fourth Street Filling Station (in the West End Historic District).

Morning: Bethabara Park

North Carolina - Winston Salem - Bethabara - Gemeinhaus

For one last Moravian morning, head to Bethabara Historic Park. This was the first settlement the Moravians built when coming to Forsyth County in 1753, so the buildings you’ll see here are some of the oldest in the area.

The park’s mission is “the documentation, preservation, interpretation, promotion, and public celebration of Winston-Salem’s 18th-century birthplace.”

North Carolina - Winston Salem - Historic Bethabara Park

This is done in a way that makes it easy for visitors to both learn the history as well as enjoy the beautiful surrounding that’s now a public park.

Start at the Visitor’s Center, especially if you want to go on a tour. Tours are $4 per adult, and visiting the park without a tour is free.

North Carolina - Winston Salem - Bethabara - Gemeinhaus

Bethabara is home to a French and Indian War-era Palisades Fort, a historic medicinal garden, and the oldest Gemeinhaus, or Moravian Church, with intact living quarters for the clergy in the US.

North Carolina - Winston Salem - Historic Bethabara Park - Stephanie

After your visit, head back to the Visitor’s Center, which has some of the best Winston-Salem souvenirs anywhere in the city (and some of the best Moravian cookie prices).

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Address: 2147 Bethabara Road Winston-Salem, NC 27106

Lunch: Sample New American Cuisine at Willow’s Bistro

Call ahead to make a reservation at this delightful farm-to-table restaurant where the food is as beautiful as it is delicious.

Address: 300 S Liberty St #125, Winston-Salem, NC 27101

Afternoon: Enjoy Bailey Park & a Little More Downtown

North Carolina - Winston Salem - Picnic in Bailey Park
A luxury picnic in Bailey Park by the Winston-Salem Picnic Lady!

Your time in Winston-Salem may be winding down, but there are still a few more shops to hit and things to taste before you can say you’re done for the day!

North Carolina - Winston Salem - Mast General Store

Head back downtown, but this time start at Mast General Store on Trade Street. 

After shop (or window shop) your way over to Baily Park and the Innovation Quarter.

Here you’ll find the delicious Black Mountain Chocolate Factory, Krankies Coffee, and Lill Dipper, a soft-serve ice creamery.

North Carolina - Winston Salem - Lill Dipper Ice Cream

Whatever you choose to purchase, sip on, or taste, bring it with you and enjoy some peace in Bailey Park. 

Dinner: End Your Winston-Salem Weekend with a Craft Beer at Foothills Brewing

North Carolina - Winston Salem - Foothills Brewing

With locally made craft beer on tap plus seriously good food and outdoor tables with great Winston-Salem vibes, this is the perfect place to unwind and celebrate your fabulous weekend!

North Carolina - Winston Salem - Foothills Brewing

I’m all about the beer cheese and the fried pickles, but everything here is a good choice. 

This is pub fare done with a bit of sophistication – but not too much!

Talk to the knowledgeable servers about the current beer selections, or just pick a flight of whatever catches your eye.

North Carolina - Winston Salem - Foothills Brewing - Beer

If you do sit outside, peak in before you leave. The restaurant is located inside a historic building. 

Check their website for special events like live music.

Brewpub Address: 638 West Fourth St. Winston-Salem, NC 27101

Good to Know: there is a tasting room at the actual brewery if you prefer your craft beer in a more educational setting. The tasting room is open Mon-Wed 4-9p, Thurs-Fri 4-10p, Sat 12-10, and Sun 12-8.

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Brewery Address: 3800 Kimwell Dr. Winston-Salem, NC 27103

What to Do in 4 Days in Winston-Salem, NC

If you have more time or you end up staying an extra day, you can spend more time in the city or go on a day trip somewhere nearby.

Go on a Day Trip from Winston-Salem, NC

If you want to go on a day trip to another popular North Carolina city, you can drive to Asheville (2.5 hours by car) or Charlotte (1.5 hours by car).

Alternatively, you could visit a nearby state park for some outdoor fun like kayaking or rock climbing or even visit drive three hours to Great Smoky Mountains National Park. 

Enjoy a Few More Winston-Salem Activities

North Carolina - Winston Salem - Bookstore in Downtown Winston-Salem

If you don’t want to spend a lot of time in the car, here are a few more popular things to do in Winston-Salem:

Do more shopping downtown at the city’s great boutiques and bookstores.

Check out one of the city’s beautiful golf courses.

See a game at Wake Forest University.

Take the kids to the Children’s Museum of Winston-Salem.

Learn about the history of Nascar at the Winston Cup Museum & Special Events Center. 

Visit tranquil Tanglewood Park in Clemmons, a small town just fifteen minutes away.

Visit the Last Shell Oil Clamshell Station, a gas station that’s now a historic landmark.

Circle Back to Anything You Missed During Your First 3 Days

North Carolina - Winston Salem - Reynolda Gardens
There’s always more to do at Reynolda!

If you found there was something you had to skip during your first three days in town, or there was something you didn’t get to enjoy as much as you would have liked, you can take the extra time to circle back!

Look for Special Winston-Salem Events

From Wake Forest basketball games to the RiverRun International Film Festival, there are lots of great special events that happen in the city throughout the year.

If you are looking for something to do in Winston-Salem this weekend that’s special or seasonal, you can check the city’s calendar as well as look at the different schools and performance venues for ideas.

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What to Do If You Only Have 2 Days in Winston-Salem?

This is tough! I love everything on this itinerary. Of course, if you only have two days, you have to make some choices!

North Carolina - Winston Salem - Bethabara - Gemeinhaus
Don’t skip Bethabara, Old Salem, or Reynolda!

I would spend less time shopping and exploring downtown and more time in Old Salem, Reynolda, and Bethabara. These are the places that are unique to Winston-Salem.

I also would make sure to see SECCA, which doesn’t take long and is a world-class museum.

North Carolina - Winston Salem - Reynolda House Museum of American Art

Plus, you can still fit in a bit of downtown time once you’ve gone to these three magical historic places.

Here’s an example of how you could fit most of this Winston-Salem itinerary in two days:

Day 1:

Old Salem

Lunch

Walk Around Downtown Arts District & ARTivity

Dinner at Foothills Brewery

Day 2:

SECCA

Reynolda Village

Lunch at Reynolda Village

Reynolda House & Gardens

Dinner at Katharine Brasserie

Walk around Bailey Park area of downtown

What to Do if You Only Have One Day in Winston-Salem?

North Carolina - Winston Salem - Old Salem Museums and Gardens - View of the 100 North Main Street

This is so tough, but I would have to make some serious choices. My ideal one-day in Winston-Salem itinerary would be:

Old Salem (3 hrs)

Bethabara (1 hr)

Lunch in Reynolda Village (1 hr)

Reynolda House and Gardens ( 3 hrs)

Walk around Downtown Arts District (1-2 hrs)

Dinner Downtown at Foothills Brewery (1 hr)

5 Things to Pack for Your Trip to North Carolina

North Carolina - Winston Salem - Foothills Brewing - Jordan and Stephanie
Don’t forget your sunglasses!

You know to bring sunscreen and sunglasses, but here are five items you do not want to forget!

First, get a guidebook like the Lonely Planet Georgia & the Carolinas. It’s not easy to find traditional guidebooks once you land.

If you will be going on a road trip around North Carolina or nearby Georgia and South Carolina, I love Lonely Planet’s Florida & the South’s Best Road Trips

USA - North Carolina - Outer Banks Stephanie
Heading to the Outer Banks? Make sure you’re prepared for the beach!

Second, make sure to bring your cell phone. You will want to stay connected during your trip, plus it will serve as a navigation system and a go-to camera. 

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I use an iPhone 12 Pro these days, but I have also used Samsung phones in the past.

Third, grab a camera. While it’s great to have a cell phone with you for quick pics, if you want to do more serious photography or take more videos, I find it nice to travel with a separate dedicated camera as well.

If I will be wrestling with my toddler on the trip, I’ll grab my Sony ZV-1, which is a powerful compact camera with great video capabilities as well. 

If it’s just me, I’ll take my Nikon (though if you’re buying a new camera I have my eye on this Sony).

North Carolina - Winston Salem - Reynolda Village - Reynolda House Gardens & Trail - Waterfall - Stephanie - Planning a trip to Winston Salem

Next, bring a waterproof bag (also knowns as a dry bag) so that you can safely bring your electronics to the beach or kayaking. (If you’ll be going to the beach, obviously!).

You don’t want to ruin your trip with a drowned cell phone or wet camera, but you also don’t want to miss out on capturing all those great beach moments with your loved ones!

Finally, bring a backup charging bank for your phone. 

Even though my new phone has an awesome battery life, I would not want to be out on a boat or a tour for the day and end up with a dead phone. 

It’s a safety issue as well as an inconvenience.

More North Carolina Travel Resources

We just love North Carolina! I’ve been five times, and I already can’t wait to go back! 

Here are all the North Carolina travel blog posts that I have to help you plan your trip around this wonderful state!

North Carolina State-Wide Guides

Best Quotes about North Carolina

National Parks in North Carolina

North Carolina City + Regional Guides

The Outer Banks

The 12 Best Outer Banks Beaches for Your East Coast Getaway

The 7 Most Charming Outer Banks Towns for Your Summer Getaway

Winston-Salem

3 Days in Winston-Salem: Itinerary for the Perfect Long Weekend in Winston-Salem, North Carolina

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17 Winston-Salem Travel Tips: Planning a Trip to Winston-Salem, North Carolina the Easy Way!

North Carolina is Included in these Round-Ups

The 50 Most Stunning Waterfalls in the US for an Epic Outdoor Getaway

The 40 Most Scenic Drives in America for Stunning Weekend Getaways

30 of the Best Historic Towns in America for a Charming Getaway

30 Historic Cities in the US to Explore on Your Next US Getaway

The 27 Most Beautiful East Coast Lighthouses & How to Visit Them!

The 7 Best College Towns in America for an Awesome Collegiate Getaway

Guidebooks I Used to Plan My Trip Around the South

These are the travel guidebooks that I used to plan my entire 5-week Southern USA road trip. I highly recommend each of them!

This is My South – written by my friend Caroline Eubanks of the eponymous blog, this book is a must-read if you plan on visiting a few places on your trip.

Lonely Planet Florida & the South’s Best Trips – this book was essential for me when I was trying to plan our road trip and understanding what was near each other and what absolutely not to miss.

Moon U.S. Civil Rights Trail: A Traveler’s Guide to the People, Places, and Events that Made the Movement – we did a lot of Civil Rights and Civil War historic sites on our trip, and if you’ll be doing any of this kind of travel, make sure to get this. 

It was invaluable for finding off-the-beaten-path sites and can’t miss Black-owned historic businesses.

Before You Leave for North Carolina – Don’t Forget About Travel Insurance!

Before you leave for your North Carolina vacation, make sure you have a valid Travel Insurance Policy because accidents happen on the road.

I like to use World Nomads when I travel, and I happily recommend them.

It’s especially important to get travel insurance whenever you are more than one hundred miles from home, hanging out in large cities, or doing outdoor activities like going to the beach or kayaking.

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17 Winston-Salem Travel Tips: Guide to Planning a Trip to Winston-Salem, North Carolina!

So basically everything fun about visiting North Carolina.

Get a travel insurance quote for your trip here.

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3 Days in Winston-Salem Itinerary for the Perfect Long Weekend in Winston-Salem, North Carolina

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