Key Takeaways:
- Winston-Salem, North Carolina, offers a unique blend of history, art, and outdoor activities that make it a great destination year-round.
- Whether you enjoy hiking, cultural experiences, or food festivals, there’s always something happening in the city.
- With a mix of free and budget-friendly attractions, Winston-Salem is an ideal place for families, solo travelers, and weekend explorers.
Table of Contents
- Explore Old Salem Museums & Gardens
- Hike at Pilot Mountain State Park
- Visit the Reynolda House Museum of American Art
- Enjoy Live Music and Events at Bailey Park
- Discover the Historic Brookstown Inn
- Stroll Through the Southeastern Center for Contemporary Art
- Sample Local Brews on the Winston-Salem Craft Beer Trail
- Attend the National Black Theatre Festival
- Walk Through the Quarry at Grant Park
- Experience the Annual RiverRun International Film Festival
Winston-Salem, North Carolina, is a city with deep historical roots and a thriving arts scene, making it a fascinating destination no matter the season. Once known as the hub of the tobacco industry, this city has evolved into a vibrant cultural center filled with museums, historic landmarks, and outdoor attractions. Whether you’re an adventure seeker, a history buff, or a foodie looking for local flavors, Winston-Salem offers something for everyone.
Visitors love this city for its balance of old and new, where cobblestone streets lead to modern breweries, and centuries-old homes sit alongside trendy coffee shops. From scenic hikes to lively festivals, there’s always an exciting way to experience Winston-Salem. If you’re planning a visit, here are ten incredible things to do in the city all year long.
1. Explore Old Salem Museums & Gardens
Step back in time with a visit to Old Salem Museums & Gardens, a living history museum that showcases life in an 18th-century Moravian settlement. Walking through this beautifully preserved district feels like entering another era, with historic buildings, costumed interpreters, and hands-on workshops. Visitors can watch traditional craftsmen at work, sample Moravian baked goods, and tour homes furnished as they were in the 1700s. The area is also home to stunning gardens, where heirloom crops and medicinal plants are grown as they were centuries ago.
Old Salem hosts special events throughout the year, including candlelit tours during the holiday season and historical reenactments in the summer. Whether you’re interested in history, architecture, or just looking for a peaceful place to explore, this district provides an immersive experience that highlights Winston-Salem’s rich past. A visit here is a must for anyone wanting to experience the city’s deep-rooted heritage firsthand.
2. Hike at Pilot Mountain State Park
For an outdoor adventure with breathtaking views, Pilot Mountain State Park is the perfect getaway just outside Winston-Salem. Known for its iconic peak that rises above the surrounding landscape, this park offers a variety of hiking trails ranging from easy walks to challenging climbs. The Jomeokee Trail provides a close-up view of the mountain’s summit, while the Grindstone Trail offers a longer hike with rewarding panoramic views.
In addition to hiking, the park is a popular spot for rock climbing, birdwatching, and picnicking. The changing seasons bring different experiences, from vibrant fall foliage to lush greenery in the spring. Whether you’re looking for a casual nature walk or a full day of outdoor activities, Pilot Mountain is a fantastic destination any time of year.
3. Visit the Reynolda House Museum of American Art
Art and history enthusiasts will appreciate a visit to the Reynolda House Museum of American Art, once the grand estate of tobacco magnate R.J. Reynolds. This beautifully preserved mansion is home to an impressive collection of American art, featuring works from the colonial period to the present. The museum’s galleries showcase pieces by renowned artists such as Georgia O’Keeffe and Grant Wood, making it a must-visit for art lovers.
Beyond the artwork, visitors can explore the estate’s stunning gardens, which are open year-round and feature seasonal blooms. The adjacent Reynolda Village offers boutique shops, cafés, and walking paths, providing the perfect place to unwind after touring the museum. Whether you’re drawn to fine art or historic architecture, Reynolda House offers a fascinating glimpse into the city’s past and cultural evolution.
4. Enjoy Live Music and Events at Bailey Park
Located in the Innovation Quarter, Bailey Park is a lively outdoor space that hosts concerts, festivals, and community gatherings all year long. The park’s modern design and open green spaces make it an ideal spot to relax, enjoy a picnic, or catch a live performance. Popular events include Friday Night Music Series, outdoor yoga sessions, and food truck rallies that showcase the best of Winston-Salem’s culinary scene.
Bailey Park is also surrounded by some of the city’s trendiest breweries and coffee shops, making it easy to grab a drink before or after an event. Whether you’re visiting for a major festival or simply looking for a casual spot to enjoy the city’s vibrant atmosphere, this park is a go-to destination for entertainment and relaxation.
5. Discover the Historic Brookstown Inn
For a unique and historic stay in Winston-Salem, book a night at The Historic Brookstown Inn. This boutique hotel is housed in a former textile mill from the 19th century, blending vintage charm with modern comforts. Each room features exposed brick walls and antique furnishings, offering guests a taste of the city’s industrial past. The inn’s cozy atmosphere, complete with complimentary wine and cheese receptions, makes it a favorite among visitors.
Even if you’re not staying overnight, the inn frequently hosts historical tours and community events, giving travelers a chance to learn more about its storied past. Located near Old Salem and downtown, it’s also a convenient starting point for exploring the city’s other attractions. Whether you’re a history lover or just looking for a unique experience, the Brookstown Inn provides an unforgettable stay in Winston-Salem.
6. Stroll Through the Southeastern Center for Contemporary Art
Art lovers will find inspiration at the Southeastern Center for Contemporary Art (SECCA), a museum dedicated to showcasing cutting-edge works from regional and national artists. Unlike traditional museums, SECCA focuses on modern and experimental pieces, featuring a rotating collection of multimedia installations, paintings, and interactive exhibits. The museum is housed in a former historic mansion, blending old-world charm with contemporary artistic expression.
Throughout the year, SECCA hosts artist talks, workshops, and community events that engage visitors in thought-provoking conversations about art and culture. Admission is free, making it an accessible destination for anyone curious about the evolving world of contemporary art. Whether you’re a seasoned art enthusiast or just looking for a unique experience, SECCA is a must-visit in Winston-Salem.
7. Sample Local Brews on the Winston-Salem Craft Beer Trail
Winston-Salem’s craft beer scene is booming, and the Winston-Salem Craft Beer Trail offers a great way to experience the city’s best breweries. The trail features a variety of local spots, from small-batch brewers to larger taprooms with extensive selections. Popular stops include Foothills Brewing, known for its well-balanced IPAs, and Wise Man Brewing, which offers a constantly changing lineup of creative brews.
Many breweries along the trail offer outdoor seating, live music, and food trucks, creating a lively social atmosphere. Whether you’re a craft beer connoisseur or just looking to try something new, the beer trail is a fun way to explore Winston-Salem’s evolving beverage culture. Grab a pint, meet local brewers, and enjoy the welcoming vibe of the city’s best taprooms.
8. Attend the National Black Theatre Festival
Every two years, Winston-Salem becomes the center of the National Black Theatre Festival (NBTF), a world-renowned event that celebrates Black artistry in theater. The festival attracts performers, playwrights, and audiences from across the country, featuring a lineup of powerful stage productions, workshops, and cultural events. It’s a must-attend experience for theater lovers and those looking to immerse themselves in African American performing arts.
Beyond the performances, the festival includes networking events, film screenings, and an electric atmosphere that fills the city with energy. Even if you’re visiting outside of festival season, Winston-Salem’s thriving theater scene offers year-round performances at venues like the NC Black Repertory Company and Hanesbrands Theatre.
9. Walk Through the Quarry at Grant Park
For a lesser-known but stunning outdoor escape, visit The Quarry at Grant Park, one of Winston-Salem’s hidden gems. This former quarry has been transformed into a scenic park with walking trails, picnic areas, and an observation deck that provides sweeping views of the deep blue quarry waters. The park is a peaceful retreat, perfect for a quiet afternoon walk or a relaxing moment in nature.
At sunset, the quarry’s reflective waters and rugged cliffs create a breathtaking scene, making it a favorite spot for photographers. With its serene atmosphere and natural beauty, this park is a great year-round destination for anyone looking to step away from the city’s hustle and enjoy a unique outdoor setting.
10. Experience the Annual RiverRun International Film Festival
Cinephiles won’t want to miss the RiverRun International Film Festival, a major event that brings independent films from around the world to Winston-Salem. Held annually in the spring, the festival screens a diverse selection of films, including documentaries, shorts, and feature-length movies. In addition to screenings, the festival hosts panel discussions, filmmaker Q&As, and networking events.
Outside of festival season, Winston-Salem has a great local film scene, with venues like a/perture cinema offering indie and foreign film screenings year-round. Whether you’re a film buff or just looking for a unique cultural experience, RiverRun is one of the city’s most exciting artistic events.
What to Do if You Have Kids?
Families visiting Winston-Salem will find plenty of kid-friendly activities throughout the city. The Kaleideum North museum is a great destination for interactive science exhibits, hands-on learning stations, and a planetarium that offers an immersive look at the stars. For outdoor fun, Hathaway Park features large playgrounds, walking trails, and plenty of green space for kids to run and play.
If your children love animals, Tanglewood Park offers horseback riding, fishing, and seasonal events like the Festival of Lights in the winter. Winston-Salem also has family-friendly festivals and street fairs throughout the year, ensuring that there’s always something fun to do with kids.
Where Can I Find Free Events in Winston-Salem North Carolina Taking Place This Weekend?
For free events in Winston-Salem this weekend, check out PlanMyWeekend.ai. This tool helps you find concerts, farmers’ markets, cultural festivals, and outdoor activities happening nearby—all at no cost. Whether you’re searching for live music, free museum days, or outdoor yoga in the park, PlanMyWeekend.ai makes it easy to discover fun activities.
Many of Winston-Salem’s historic sites and parks also host free events throughout the year, from guided tours to public art installations. Simply enter your location on the site to find the best upcoming free activities.
Final Thoughts
Winston-Salem is a city filled with culture, history, and outdoor adventure, making it a fantastic destination at any time of the year. Whether you’re exploring its historic districts, hiking scenic trails, or attending one of its many festivals, there’s always something to experience.
With its welcoming atmosphere and diverse attractions, Winston-Salem offers the perfect mix of relaxation and excitement. Whether you’re visiting for a weekend getaway or planning an extended stay, this city has something for every traveler. Start planning your trip today and discover all the amazing things Winston-Salem has to offer.
Author: Dejon Brooks
Dejon Brooks is an entrepreneur who founded Trend Watchers with his life savings. Aged 24, Dejon has turned Trend Watchers into a successful business. After reaching over 150M+ people on his personal accounts, he now spends his time growing Planmyweekend.ai
