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Oct. 1–4

Reynolda: Chimes of Freedom. Reynolda pairs its fall exhibition with a four-day concert series celebrating folk singers and the movements they soundtracked. The run opens with a gala Thursday night and continues with evening performances Friday and Saturday from 7:30–9:30 p.m., plus a VIP performance followed by a tented dinner on the front lawn.

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Oct. 2–11

Carolina Classic Fair. North Carolina's second-largest fair returns to the Winston-Salem Fairgrounds for its 144th year with the theme "Red White and Moo," a nod to the nation's 250th birthday. Ten days of rides, fair food, livestock shows, and competitive exhibits — plus the butter sculpture, the chainsaw carvers, and the racing pigs.

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Oct. 3

Kernersville Oktoberfest. 3–6 p.m. Now in its 16th year, Körner's Folly's signature fundraiser pours German, Oktoberfest, and pumpkin brews alongside small bites donated by area restaurants. Each ticket includes tastings, a souvenir glass, and a self-guided tour of the 22-room 1880 house. Tickets start at $40; this is a 21+ event, and it sells out most years.

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Oct. 3

Bailey Park Latin Fest. 5–10 p.m. Bailey Park closes out Hispanic Heritage Month with an open-air night of salsa, bachata, and folklórico dance performances, a live band, and food trucks serving dishes from across Latin America. Bring a blanket or lawn chair. Admission is free and all ages are welcome.

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Oct. 3, 31 

Wake Forest Football. The Demon Deacons have two Saturday home games at Allegacy Stadium this month, both against ACC opponents. Game times are still TBD at this point. For more on the Deacs 2026 season, including parking, tailgating, and ticket info, check out our WFU Football Overview here. 

► Oct 03 – Stanford; Family Weekend

► Oct 18 – Virginia; Salute to Service

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Oct. 4

Salem Band Concert: 1976 Retrospective. 3–4:30 p.m. Fifty years after the Bicentennial, Salem Band revisits the music of 1976 — Saturday Night Fever, ABBA, Elton John, and songs from Evita and A Chorus Line. Held in Hanes Auditorium at Salem College; the concert is free, and disco attire is encouraged.

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Oct. 4 

Trade Street Farmers Market.(monthly) 10 a.m.–2 p.m. Trade Street closes between Fifth and Sixth streets for a food-and-beverage-only market filled with produce, baked goods, prepared foods, and specialty drinks. Free.

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Oct. 9, 23

Innovation & Cinema. 7 p.m. Bailey Park's free outdoor movie series wraps its season with two October screenings, both built around this year's need-for-speed theme. Films start around sunset, with food trucks and Incendiary Brewing drinks available an hour beforehand. Bring a low-slung chair or blanket; leashed dogs welcome.

► Oct. 09 – Ford v Ferrari (2019)

► Oct. 23 – Tron Legacy (2010)

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Oct. 9–18

Theatre Alliance: Young Frankenstein. Horror meets hilarity in this stage adaptation of the cult-classic film, following Dr. Frederick Frankenstein as he sets out to reanimate life and finds mostly chaos instead. Expect the wit, the musical numbers, and the larger-than-life characters. Shows are at the Theatre Alliance, 650 W. Sixth St. Tickets $23–$25.

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Oct. 10

Reynolda Community Day: Picturing Freedom. 9:30 a.m.–4:30 p.m. Reynolda marks the nation's 250th with a day built around freedom of expression, with art activities on the lawn and performances running from 10 a.m. to 2 p.m. Pair it with the exhibits Flash Point and Art & Democracy, both on view. Museum admission is free all day.

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Oct. 10

Oyster Roast at Shelton Vineyards. 2–5 p.m. The Farmhouse at Shelton Vineyards hosts an afternoon of freshly shucked North Carolina oysters and a traditional Low Country boil, set against the Yadkin Valley hills. Live music and a silent auction round it out, with proceeds benefiting Mountain Valley. Tickets are $75 and include two beverages for guests 21 and over; last year's inaugural event sold out, so book early.

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Oct. 10

WS Symphony: Aoife O'Donovan. The Grammy-winning singer-songwriter brings her blend of folk, roots, and bluegrass to R.J. Reynolds Auditorium for a one-night-only performance. The program pairs favorites like "Briar Rose" and "Magic Hour" with selections from her latest album, including the suffrage anthem "America, Come," performed with girls from the Winston-Salem Choral Academy.

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Oct. 10, 17  

WSSU Football. 1 p.m. kickoffs. The Rams continue their 2026 season with two home games on back-to-back Saturdays in October. General admission tickets start around $30 and can be purchased at wssurams.com. For things to know this season, check out our WSSU Football Overview here.

► Oct. 10 – Bowie State

► Oct. 17 – Bluefield State: Senior Day

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Oct. 13

Swan Lake by United European Ballet. 7 p.m. The company brings Tchaikovsky's most famous score to R.J. Reynolds Auditorium in the original Petipa and Ivanov choreography, with more than 200 handcrafted costumes and sets built for this North American tour. Two acts and one intermission, including the Dance of the Little Swans and Odile's 32 fouettés. Suitable for ages 3 and up.

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Oct. 16

Bailey Park Hangs: Real Companion. 5–8 p.m. NCMA Winston-Salem's outdoor concert series welcomes Boone-based duo Real Companion to Bailey Park, with mellow guitar, sharp lyrics, and a portrait of small-town southern life. Doors and food trucks open at 5 p.m., music from 6–8 p.m. Admission is free; outside food is welcome, but not alcohol.

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Oct. 16–Nov. 1

Little Theatre: Disney's Frozen. 7 p.m. The Little Theatre of Winston-Salem presents the global phenomenon based on the hit film — a magical tale of two royal sisters, with all the film's songs plus new music for the stage. Shows will be held at Little Theatre's new stage at 4015 Brownsboro Road. All shows at 7 p.m. except Sunday matinees (2 p.m.). Tickets start at $14.50.

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Oct. 17

Yadkin Valley Grape Festival. 11 a.m.–5 p.m. Twenty-five minutes from downtown, Yadkinville hosts its 22nd annual celebration of the region's wine country with pours from Yadkin Valley wineries, food trucks, live music, and local craft vendors. Admission is free; tasting tickets include run $20 in advance or $25 at the gate.

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Oct. 18

Monster Dash & Goblin Hop. 2–4 p.m. Kids in costume "goblin hop" their way down the Village Point Greenway in Clemmons, where local businesses and organizations set up games, crafts, and giveaways at stops along the route. Bring a goodie bag. The event is free; park at Morgan Elementary School.

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Oct. 18  

Tour Pour Du Jour at Graylyn. 4–6 p.m. Explore Graylyn’s 1932 Manor House on a guided tour that concludes with wine and light appetizers in the Library. Tickets are $60.

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Oct. 21

WFU Face to Face: Ken Burns. 7:30–9 p.m. The documentary filmmaker behind "The Civil War," "Baseball," and "The Vietnam War" comes to Wait Chapel for a keynote moderated by longtime New York Times journalist Frank Bruni. A 17-time Emmy winner, Burns arrives on the heels of his latest film, "The American Revolution."

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Oct. 23

Witches Walk & Night Market. 6–10 p.m. Dress in your best witchy attire and stroll the Arts District for this third-annual Halloween tradition, starting at CasaShanti on Trade Street. Collect letters from participating shops to unscramble a secret word and earn a raffle entry, then browse the night market for vendors, pumpkin carving, trick-or-treating, and live music. Free, and pets are welcome.

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Oct. 23–31

Theatre Alliance: Rocky Horror Show. A Halloween tradition returns as Theatre Alliance stages the cult-classic musical inspired by the 1975 film. Known for is campy comedy and catchy songs, the show promises plenty of thrills and audience participation. Tickets are $25.

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Oct. 24

Boo! at Bethabara. 1:30–4:30 p.m. Spooky songs in the 1798 Gemeinhaus, a walk to God's Acre to meet a few "spirits" of Bethabara's past, and ghost stories under a tent from storyteller Cynthia Moore Brown. Kids can make a corn husk doll, watch Glen Yost's sleight-of-hand magic show, play Colonial games, get their faces painted, and more. Admission is free.

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Oct. 24

Books & Brews at Fiddlin' Fish. 2–6 p.m. Four of the area's independent booksellers — Bookmarks, The Bookhouse, Main & Mountain, and The Purple Honeybee Bookmobile — set up shop at Fiddlin' Fish Brewing with curated selections to browse. Raise a glass to the city's indy bookstores.

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Oct. 24

Ghoul Moon Festival. 4–10 p.m. The West Salem Art Hotel teams with The Full Moon Crew for a night of artists, makers, and vintage vendors, plus live music, performances, and hands-on workshops led by local artists and nonprofits. Spooky contests with real prizes, bites from local pop-ups and food trucks, and plenty to drink.

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Oct. 25

NC Bridal & Wedding Expo. 1:30–5 p.m. Planning a wedding? The Benton Convention Center fills with vendors and specialists ready to talk through everything from black-tie formal to barefoot-on-the-beach. A useful afternoon whether you're just starting or deep in the details.

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Oct. 31

M&C Halloween Craft Fest. 10 a.m.–3 p.m. Spend Halloween morning in downtown Kernersville, where the iconic Musten & Crutchfield Food Market hosts a market of handmade goods from local makers, plus food trucks and festive family fun.

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Throughout the Month

 

Cobblestone Farmers Market 

This popular producer-only market regularly features 45-50 local farms, bakers, cheesemakers, and more. Offerings include sustainably raised meats, herbs, baked goods, and fresh produce, all held to high standards. Held near Old Salem at 1007 S. Marshall St. (map). Fall hours are Wednesdays, 8:30–11 a.m., and Saturdays, 8:30–noon.

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Fall Exhibits at Reynolda

Opening Sept. 17, Flash Point: The Civil Rights Photography of Danny Lyon, brings together more than 50 photographs from inside the movement — sit-ins, Freedom Rides, and the March on Washington — but also the jail cells, planning rooms, and quiet moments between. Reynolda will also hold a Curator Talk with art historian Ashley Givens on Oct. 28 (link).

Also on view this fall, Art & Democracy draws on Reynolda's collection to trace the nation's history and its shifting ideals. Both exhibits rare included with museum admission.

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NCMA Exhibit: Process as Practice 

The second show in NCMA's new downtown space brings together three artists who call Western North Carolina home. Leah Smith draws with ink and cotton to explore how separate pieces resolve into a whole. Kimberly English builds objects from thread that hold together while each part stays distinct. Erin Canady works with water and graphite to capture the passage of time. All three are interested in how materials join, gather, and change.

The show is on display Sept. 17–Nov 29. Admission is free.

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Taste of Art at Sawtooth 

These popular one-night workshops invite guests to explore mediums such as glass, ceramics, jewelry, and fibers. Each class includes hands-on instruction and the chance to create artwork to take home. Most classes are held on Fridays, 6–8 p.m., at Sawtooth School. Additional classes also occur at The Generations Center (114 W. 30th St.) on various days. Classes start at $45 and include materials.

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Concerts at The Ramkat 

The Ramkat, downtown's 1,000-capacity music venue, hosts an impressive lineup of regional and national acts this month, with additional shows at Gas Hill, Ramkat's intimate 100-capacity venue. Mainstage highlights include:

► Oct 02 — Paul Thorn
Former pro boxer-turned-Southern rock and blues singer-songwriter.

► Oct 09 — Chris Knight | Mic Harrison
Kentucky singer-songwriter known for his gritty, authentic country-folk. 

► Oct 15 — Joshua Ray Walker 
Texas honkytonk singer-songwriter with a soaring voice and inspiring story.  

► Oct 16–17 — The SteelDrivers
Grammy-winning "bluegrass with a blues soul." Two-night ticket discounts are available.

► Oct 21 — John Oates
Half of the best-selling duo in pop history, Hall & Oates, now digging into roots and blues.

► Oct 22 — AJ Lee & Blue Summit
Award-winning acoustic band blending bluegrass with country, soul, and Americana.

► Oct 24 — Rumours ATL: Fleetwood Mac Tribute
Atlanta outfit recreating the Rumours-era hits, harmonies and all.

►Oct 29 — Dirty Logic Steely Dan Tribute
Asheville all-stars with horn section tackling the Dan's jazz-rock.

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