Fall in Winston-Salem beckons with the sights, sounds, and flavors of the autumn season. Explore historic homes transformed into awe-inspiring art museums along the Reynolda Mile. Shop one-of-a-kind handcrafted works at the 58th annual Piedmont Craftsmen’s Fair, travel back for a tailgate weekend, or pick the perfect foliage backdrop in historic Old Salem. In the nearby Yadkin Valley, sip, swirl, and savor the harvest of more than 45 wineries. Check out our fall lineup below to start planning your seasonal getaway trip to Winston-Salem.

Calendar of Top Festivals and Events This Fall:

*Click Here to View All Upcoming Events

Turn Game Day into a Winston-Salem Getaway

Winston-Salem is proudly home to six prestigious colleges and universities, and we invite you to huddle up for fall football. Click here for game day schedules for Wake Forest University and Winston-Salem State University.

7 Reasons You’ll Fall for Winston-Salem

Gear up and travel back to Winston-Salem for the ultimate seasonal retreat full of adventure and relaxation. Take in the stunning showcase of fall colors in and around our hip, historic city… and cross the following “can’t miss” experiences off of your Winston-Salem autumn bucket list! #LookForwardFallBack

  1. Embark on an Autumn Adventure at Salem Lake
    Conveniently tucked away and just a 10-minute jaunt from downtown Winston-Salem, Salem Lake is surrounded by lush woods – making the shaded seven-mile loop trail ideal for a comfortable autumn hike, bike, or stroll during leaf-peeping season. Bike rentals are available through FLOWBIKES Bikeshare, with a docking station at Salem Lake Trail for a trek around the 365-acre lake. Get on the water with kayak and Jon-boat rentals at the Salem Lake Marina Center, or fish to your heart’s content off of the 300 ft. pier offering pristine lakeside views.

    Salem Lake
  2. Climb to New Heights at Hanging Rock and Pilot Mountain State Parks
    From the foothills to the scenic summits of nearby Pilot Mountain and Hanging Rock State Parks, Winston-Salem is the perfect place to escape from the ordinary and view magnificent fall colors. Choose your own adventure from beginner to advanced, whether admiring Pilot Mountain’s iconic peak on foot or embarking on an exhilarating trek along the Hanging Rock Trail, where awe-inspiring Blue Ridge Mountain views await. Both state parks are a quick jaunt from Winston-Salem, which offers scenic city-side strolls with over 20 miles of trails in the sprawling downtown area. *Due to the popularity of Hanging Rock and Pilot Mountain State Parks during peak foliage, park rangers encourage visitors to explore during the week to avoid heavy weekend traffic.

    Hanging Rock State Park
  3. Savor Our History One Bite at a Time
    In Winston-Salem, baking is an art form. Treat your tastebuds to warm, sweet, and savory selections of fresh-baked autumn treats at our more than a dozen downtown bakeries. Pumpkin spice (and other fall-infused spices and flavors) will tempt your palate at some of downtown’s must-taste stops for sweet tooths and savory fans alike. Indulge in an Instagram-worthy goodie (or two) from Louie and Honey’s Kitchen, Black Mountain Chocolate Bar, Camino Bakery, Bobby Boy Bakeshop, and Humble Bee Shoppe. And don’t forget to swing by Winkler Bakery, one of the oldest operating bakeries in the country, which gladly serves up gooey Moravian sugar cake and whisper-thin Moravian cookies in the heart of Old Salem.

    Winkler Bakery
  4. Relish Magnificent Fall Foliage along the Reynolda Mile
    This fall, discover Winston-Salem’s charming Reynolda Mile, home to historic homes, lush heirloom gardens, and a boutique shopping village. Just minutes from Winston-Salem’s hip downtown, the maple canopied Reynolda Mile is a welcomed step back in time. Admire works of art at Reynolda House Museum of American Art, the pristine country estate of R.J. and Katharine Reynolds, then tour the adjacent formal gardens and 1913 greenhouse. The historic charm continues in Reynolda Village, where you’re invited to shop seasonal finds at local boutiques and galleries and savor autumn-inspired dishes at a handful of eateries. Your self-guided fall foliage tour continues at the neighboring 55-acre Graylyn Estate, a stunning 1932 historic home-turned-exclusive hotel, and the expansive grounds of Southeastern Center for Contemporary Art (SECCA).

    Reynolda Mile
  5. Discover the Flavors of Fall on our “Craft Draft” Crawl
    With nine downtown craft breweries within walking distance of one another, Winston-Salem is an imbiber’s paradise for sampling the season’s best brews. Tap into our locally crafted beer scene with special autumn releases such as Foothills Brewing’s Pumpkin Ale, a crisp, dry ale that uses pumpkin pie spices brewed with real pumpkin and a blend of malts. Other “crafty” stops include Hoots Roller Bar & Beer Co., Incendiary Brewing Company, Fiddlin’ Fish Brewing Company, Hoots Satellite, Radar Brewing Company, Joymongers Barrel Hall, Small Batch Beer Co., and Wise Man Brewing.

    Pumpkin Ale at Foothills
  6. Dig into Our History at Old Salem Museums & Gardens
    Travel back in time this fall at Old Salem Museums & Gardens, a charming 1766 Moravian settlement that offers visitors a hands-on exploration of 18th and 19th-century traditions. Seek out the perfect fall foliage backdrop beside the towering maple trees found outside the 1771 Miksch House. Marvel at the fiery glow of the Gingko Tree in God’s Acre, a Moravian cemetery where rolling hills are dotted with identical white marble headstones. Discover the Miksch heirloom gardens and the Single Brothers’ Garden, an award-winning restoration garden and the largest interpreted garden in Old Salem, where seeds are saved from one harvest to replant for the next. *Please note that Old Salem’s current operating hours (Wednesday through Saturday, 10 a.m. – 2 p.m.) have been modified in light of COVID-19 to ensure a safer visitor experience.

    Boys’ School at Old Salem
  7. Winston-Salem’s Favorite Fall Color? Cabernet, of course!

As the gateway to the nearby Yadkin Valley wine region, Winston-Salem is nestled amidst more than 45 wineries within an hour’s drive. Raise a glass (or two) at one (or more) of our award-winning vineyards, which also happen to be prime spots for fall leaf peeping. Three can’t miss vino-tastic fall excursions include stops at Divine Llama Vineyards, Raffaldini Vineyards & Winery, and JOLO Winery & Vineyards for their unique atmospheres and memorable tastings. At Divine Llama, a host of furry, four-legged beauties are ready to trek you through some of the finest fall colors, just 20 minutes outside Winston-Salem. “Take a hike” with Jay Raffaldini, owner of Raffaldini Vineyards, throughout his picturesque “Tuscany-esque” winery followed by a hearty luncheon paired with wine. Nestled in the undulating hills of the Piedmont, JOLO offers majestic views of Pilot Mountain State Park along with delectable dining at its on-site restaurant, End Posts.


Fall Hotel Getaway Packages

With so much to see and do this fall in Winston-Salem, you’re going to want to stay awhile. With more than 50 hotels and a variety of seasonal hotel getaway packages, you’re just a few clicks away from “falling in love” with Winston-Salem. Click Here to Learn More and Book Now!