Ashland Dance Academy’s Thriller Flash Mob during Ashland Halloween, 2024
🍂 Recurring October Fun in Ashland & Hanover
🎲 Trivia Night Every Wednesday at Casa Herradura
Gather your crew and flex those brain muscles every Wednesday at 7 PM in the heart of Ashland! 🍻 Casa Herradura keeps it lively with $5 OFF beer or margarita towers while you play. Bring the brains, win the prizes, and toast to the best trivia night in the Center of the Universe.
📍 428 England St, Ashland, VA
🎶 Singo Night Thursdays at Casa Herradura
What’s Singo? Think bingo… but with a soundtrack! 🎤 Every Thursday at 7 PM, Casa Herradura turns up the tunes for a night of music, laughs, and prizes. Sing along, tap your toes, and test your luck. Spoiler: no actual singing required (but we bet you’ll be humming).
📍 428 England St, Ashland, VA
🐾 Patio Pup Menus at Homemades by Suzanne
Your pup deserves patio dining, too! Homemades by Suzanne rolls out their VIP (Very Important Pup) Menu on the patio, complete with Grilled Chicken Chunks, Carrots & Berries, and whipped cream + toy for just $10. 🐶 All proceeds benefit the Hanover Humane Society, so every bite does good.
📍 102 N Railroad Ave, Ashland | ☎️ 804-798-8331
🗝️ Red Vein Escape Adventures (Wed–Sat)
Escape the ordinary with immersive escape room adventures at RED VEIN Escape. Open Wednesday through Saturday, this Ashland gem brings spooky thrills, puzzles, and movie-set-worthy rooms to life year-round. Perfect for date night, family fun, or testing your team skills!
📍 108 Robinson St, Ashland
🔗 Reserve your spot
👻 Haunted History Tours (Fridays & Saturdays, 7 PM)
Take a lantern-lit stroll through Ashland’s past on the Haunted History Tours, led by local storytellers and businesses who know all the ghostly gossip. 👻 Step into the spooky side of town Friday and Saturday nights at 7 PM with starting point at RED VEIN Escape.
📍 108 Robinson St, Ashland
🔗 Reserve your spot
🎨 Creating Calm: Expressive Art Therapy Group
Twice-monthly sessions designed to help release stress and anxiety through creativity. 🎨 Hosted by Your Path Counseling Center at the Montpelier Center for the Arts, these workshops invite you to relax, paint, and play with art in a supportive setting.
🗓️ October 2, 16, & 30 (6–8:30 PM)
💵 $45 per session
👉 Register here: montpeliercenter.org/classes
🍁 October 2025 Events
🪦 Thursday, October 2 – Woodland Cemetery Walking Tour
Step back in time with historian Susan Tucker for a twilight tour of Woodland Cemetery. Ashland’s history comes alive as you hear stories of the people who shaped this community. End the evening with a new appreciation for our town’s heritage.
📅 Thursday, October 2 | ⏰ 5:30 PM
📍 Woodland Cemetery, Ashland
👉 Registration required
🎬 October 3–5 – “The Official Release Party of a Showgirl” at Ashland Theatre
Swifties, assemble! 🎤 Don’t miss Taylor Swift on the big screen with the world premiere of The Fate of Ophelia music video, behind-the-scenes footage, lyric videos, and personal reflections from her 12th studio album The Life of a Showgirl. Three nights only at the Ashland Theatre!
📅 October 3–5
📍 205 England St, Ashland
🔗 Tickets here
🎶 Friday, October 3 – “REVOLUTIONARY!” Concert at Randolph-Macon
The RMC Wind Ensemble & Symphony Orchestra joins forces with special guests, the VCU Health Wind Ensemble & Orchestra, for a stirring night of music. Experience the power of live performance in Blackwell Auditorium.
📅 Friday, October 3 | ⏰ 7 PM
📍 Randolph-Macon Center for the Performing Arts, Ashland
🎭 October 4–5 – The Fabulous Divas of Hollywood
Alan Palmer brings the glamour, parody, and costumes in a satirical tribute to Hollywood’s greatest leading ladies. Expect wigs, laughter, and sparkle at 110 Thompson Street.
📅 Saturday, October 4 at 7:30 PM & Sunday, October 5 at 2:00 PM
📍 110 Thompson St, Ashland
🔗 Get tickets
🎣 October 4–5 – Green Top Outdoor Expo
From fishing gear to hunting demos, the Green Top Outdoor Expo is back for two days of everything outdoors. Vendors, exhibits, and family fun await!
📅 Saturday & Sunday, October 4–5
📍 10150 Lakeridge Parkway, Ashland
🔗 Details here
🎃 Thursday, October 9 – Haunted House & “Halloween” at Ashland Theatre
One night only! Brave the haunted halls of the Ashland Theatre, meet eerie characters from classic horror films, then settle in for a screening of John Carpenter’s Halloween (8:10 PM). Expect treats, cocktails, and a night of thrills.
📅 Thursday, October 9 | ⏰ Haunted House 6:30 PM, Movie 8:10 PM
📍 205 England St, Ashland
🔗 ashlandtheatre.org
🎶 Thursday, October 9 – Concert Choir & Chamber Singers’ Fall Concert
Step into an evening of harmony with Randolph-Macon’s Concert Choir and Chamber Singers as they present IN ENGLISH SONG: A Choral Journey from Renaissance Roots to Contemporary Voices. From the sacred stillness of Tallis to the rhythm of spirituals and gospel, this free concert celebrates the way choral music connects and inspires across centuries.
📅 Thursday, October 9 | ⏰ 7–8 PM
📍 Randolph-Macon College, Blackwell Auditorium
💵 Free & open to the public
🧠 Thursday, October 9 – Museum Trivia Night
Join the Ashland Museum for outdoor trivia fun in the Beer Garden behind Origin Beer. Puzzles, brain-teasers, and community laughs await. (Check AshlandMuseum.org for rain location.)
📅 Thursday, October 9 | ⏰ 6 PM
🎓 Friday, October 10 – Tour the Original Randolph-Macon Campus
Take a step back in time and walk the grounds of the original Randolph-Macon College in Boydton, VA. From 8 AM to 4 PM, you’ll explore the site where RMC began and learn what student life was like in pre–Civil War Virginia. This special trip is free, but space is limited—so be sure to reserve your spot!
📅 Friday, October 10 | ⏰ 8 AM–4 PM
📍 Boydton, VA
✉️ Reservations required by October 5 | Email kendragrimes@rmc.edu
👶 Saturday, October 11 – Toddler Takeover at Ashland Theatre
Parents, this one’s for you! Bring kiddos (ages 1 month to 6 years) for cartoons, lights-on fun, and snacks. Free entry thanks to T-Mobile.
📅 Saturday, October 11 | ⏰ 10 AM
📍 205 England St, Ashland
🔗 ashlandtheatre.org
🎨 Saturday, October 11 – Plein Air in Ashland
Pick up a brush and paint the autumn landscape as part of this fundraiser for Hanover Arts & Activities Center. Beginners welcome with an instructor’s help!
📅 Saturday, October 11 | ⏰ 10 AM–1 PM
📍 12991 Fairview Ct, Ashland
🔗 hanoverarts.net
🎥 Saturday, October 11 – “The Last Class” at Ashland Theatre
Follow Robert Reich in his final lecture at UC Berkeley—an inspiring story of teaching, activism, and hope for the next generation.
📅 Saturday, October 11 | ⏰ 7 PM
📍 Ashland Theatre
🔗 ashlandtheatre.org
🎬 Monday, October 13 – Winchester ’73 (75¢ Movie!)
Classic film, classic price! Watch James Stewart’s Winchester ’73 for just 75¢ a ticket, thanks to Dominion Energy.
📅 Monday, October 13 | ⏰ 7 PM
📍 Ashland Theatre
🔗 ashlandtheatre.org
🌱 Wednesday, October 15 – Ashland Garden Club Luncheon
Enjoy a day of learning with guest speaker Kevin Engel on regenerative farming, plus silent auction, raffle, and luncheon at Hanover Tavern.
📅 Wednesday, October 15 | ⏰ 10 AM–2 PM
📍 Hanover Tavern
💵 $45 | 🔗 Tickets here
📚 Wednesday, October 15 – Calendar Art Submission Deadline
Artists of all ages: submit your artwork for Ashland’s 2026 Calendar & Annual Report! Celebrate the character, people, and places of our town.
📅 Wednesday, October 15 (deadline)
🔗 ashlandva.info/2026calendar
🎉 Wednesday, October 16 – Montpelier Rec Center Ribbon Cutting
Celebrate Hanover’s newest hub for sports, learning, and community with a ribbon-cutting and open house. Explore the gym, library, crafts, and more!
📅 Wednesday, October 16 | ⏰ 10 AM
📍 15302 Clazemont Rd, Montpelier
🎥 Friday, October 17 – Night of the Living Dead at Ashland Theatre
One night only! The 1968 zombie classic takes over the big screen. Dare to watch the dead rise again…
📅 Friday, October 17 | ⏰ 7 PM
📍 Ashland Theatre
🔗 ashlandtheatre.org
🎃 Friday, October 17 – Cobbtoberfest (FREE Festival)
Family fun returns with bluegrass, face painting, hayrides, pumpkin decorating, bounce house, and more—all to benefit Imprint.
📅 Friday, October 17 | ⏰ 5 PM
📍 1000 Technology Park Dr, Glen Allen
🔗 Cobbtoberfest info
🚗 Saturday, October 18 – 5th Annual HOGtoberfest Car Show
Car lovers unite! See vintage rides, live music, food trucks, silent auction, and more—all to benefit the Vasculitis Foundation.
📅 Saturday, October 18 | ⏰ 11 AM
📍 16300 Jefferson Hwy, Bumpass
🔗 Event info
🎭 Saturday, October 18 – Rocky Horror Picture Show (Shadow Cast!)
Break out the fishnets—it’s time to do the Time Warp again! Catch the cult classic with live shadow cast performance and $5 prop bags.
📅 Saturday, October 18 | ⏰ 8 PM
📍 Ashland Theatre
🔗 ashlandtheatre.org
🐦 Sunday, October 19 – Hitchcock’s “The Birds” at Ashland Theatre
One of the scariest films ever made—watch Hitchcock’s feathered masterpiece on the big screen.
📅 Sunday, October 19 | ⏰ 2 PM
📍 Ashland Theatre
🔗 ashlandtheatre.org
🎼 Sunday, October 19 – The Richmond Symphony: Wagner & Haydn
The Richmond Symphony returns to Randolph-Macon for an afternoon of bold and expressive music under Associate Conductor Hae Lee. Enjoy Beethoven’s dramatic Overture to Coriolan, Saint-Georges’ elegant Sarabande et Riguadon, Wagner’s tender Siegfried Idyll, and Haydn’s lively Symphony No. 87. Your ticket also includes a pre-concert talk at 2 PM.
📅 Sunday, October 19 | ⏰ 3–4:30 PM (Pre-talk at 2 PM)
📍 Randolph-Macon College, Blackwell Auditorium
🎟️ Get tickets
🧶 Sunday, October 19 – Knit at Night: Practical Magic
Grab your yarn, your neck light, and your coven—knit and crochet while watching Practical Magic on the big screen. Non-knitters welcome too!
📅 Sunday, October 19 | ⏰ 6 PM
📍 Ashland Theatre
🔗 ashlandtheatre.org
🎙️ October 20–24 – Foster Fest On the Mic
Turn up the volume for Foster Fest On the Mic, a weeklong radio celebration sharing the powerful stories of foster youth, families, and the superheroes who advocate for them. Across Central Virginia, more than 1.3 million listeners will hear voices that deserve to be amplified—reminding us all that community builds families. 🌟 Sponsorships not only support these stories but also connect you to big benefits while making a real difference.
📅 Monday–Friday, October 20–24
📍 On-air across Central Virginia
🔗 Learn more & sponsor
⛳ Monday, October 20 – Hanover Chamber Foundation Golf Tournament
Captain’s Choice play, contests, prizes, and a chance at the Champion’s Trophy—all while raising funds for the Chamber Foundation.
📅 Monday, October 20
🔗 Register here
📚 Monday, October 20 – Book Talk: The Woman They Could Not Silence
From bestselling author Kate Moore (The Radium Girls) comes the remarkable true story of Elizabeth Packard, a woman committed to an asylum in 1860 by her husband—simply for daring to speak her mind. Discover how her courage sparked change for women’s rights and human freedom. Join us for dessert at 6:30, followed by this inspiring talk at 7 PM.
📅 Monday, October 20 | ⏰ 7–8:30 PM (Dessert reception at 6:30)
📍 Birdsong Hall, 2nd Floor, Randolph-Macon College
👉 RSVP by Oct. 13 for in-person or Oct. 16 for virtual
🔗 Register here
💵 Free & open to the public
🌸 Wed, October 22 – Groovy Ghosts Floral Workshop
Who says spooky can’t be stylish? Join Bree Mar Flower Farm for Groovy Ghosts—a Halloween-inspired floral design workshop. Expect funky blooms, unexpected color combos, sips, and snacks while you create a playful fall arrangement. No experience needed—just bring your best ghostly vibes!
📅 Thursday, October 2 | ⏰ 6:30–8:30 PM
📍 Dominion Energy Innovation Center, 201 Duncan St, Ashland
🔗 Reserve your spot
🎃 Thursday, October 23 – Pumpkins on Parade at Ashland Elementary
Decorated pumpkins, book fair, raffles, food trucks, and kid-friendly fun. Vote for your favorite pumpkin design and enjoy community vibes.
📅 Thursday, October 23 | ⏰ 5–7 PM
📍 201 Archie Cannon Dr, Ashland
📧 ashlandespto@gmail.com
👻 Thursday, October 23 – “Poltergeist” at Ashland Theatre
Spooky season staple! Join us for a screening of the 1982 classic thriller where the TV isn’t the only thing haunted.
📅 Thursday, October 23 | ⏰ 7 PM
📍 Ashland Theatre
🔗 ashlandtheatre.org
🔪 Friday, October 24 – “Psycho” at Ashland Theatre
Check into the Bates Motel… if you dare. Hitchcock’s horror masterpiece returns to the big screen for one unforgettable night.
📅 Friday, October 24 | ⏰ 7 PM
📍 Ashland Theatre
🔗 ashlandtheatre.org
🧟 Saturday, October 25 – Meadowgate Alpacas Thriller Dance Party
Dance with alpacas (yes, alpacas!) while learning Michael Jackson’s Thriller moves. Costumes encouraged, with prizes for the best.
📅 Saturday, October 25 | ⏰ 3:30 PM
📍 Meadowgate Alpacas, Hanover
🔗 Get tickets
🎨 Saturday, October 25 – Arc of Hanover Warehouse Sale
Fill a bag for $5 at this beloved sale, plus browse a community yard sale in the parking lot. Bargains galore!
📅 Saturday, October 25 | ⏰ 10 AM–2 PM
📍 10193 Washington Hwy, Glen Allen
🔗 thearcofhanover.org
🍷 Saturday, October 25 – Off the Rails: Boos, Brews & BBQ Festival
Sip, savor, and celebrate! Enjoy local beer, wine, BBQ, live music, vendors, lawn games, and a costume contest at Hanover Arts & Activities Center.
📅 Saturday, October 25 | ⏰ 3–7 PM
📍 500 S Center St, Ashland
💵 $15/person | 🔗 hanoverarts.net
🎓 October 25–26 – RMC Career Boot Camp Volunteer Opportunities
Mentor the next generation! Volunteer at RMC’s Boot Camp with mock interviews, etiquette dinners, and networking.
📅 Saturday, October 25 (5:30–8 PM) & Sunday, October 26 (10:45 AM–3 PM)
🔗 Register here
🖼️ Sunday, October 26 – History Talk: Finding Lockwood
Join Evan Dwyer for a deep dive into Hanover history with the story of Lockwood, the 1800s farmhouse tied to Robert E. Lee and local preservation.
📅 Sunday, October 26 | ⏰ 4 PM
📍 Truist Theatre, RMC Brock Commons
🚗 Sunday, October 26 – Trunk or Treat & Car Show at Gwathmey Baptist
Double the fun at Gwathmey Baptist Church’s annual Trunk or Treat and Car Show! 🍭 Kids can fill their bags with candy from decorated trunks, while families enjoy classic cars, s’mores by the fire pit, a hayride, popcorn, and more. It’s small-town fall fun at its finest.
📅 Sunday, October 26 | ⏰ 5 PM
📍 11232 Gwathmey Church Rd, Ashland, VA
🔗 gwathmeybaptist.com
🗳️ Tuesday, October 28 – Senior Law Day
Free legal services for seniors and individuals with disabilities, including wills, advance medical directives, and power of attorney. Registration required.
📅 Tuesday, October 28
☎️ Register: Call Candi May at 804-871-0225
🍬 Tuesday, October 28 – Trunk & Treat at Tompkins Plaza
Grab your costumes and candy bags—Trunk & Treat is rolling into Tompkins Plaza for an evening of family fun! 🎃 Expect music, a scavenger hunt, trick-or-treating, and delightful surprises for all ages. Hosted by Root Modern Dentistry and Tompkins Jewelers, this community celebration is the perfect way to get into the Halloween spirit.
📅 Tuesday, October 28 | ⏰ 5–7:30 PM
📍 250 N Washington Hwy, Ashland, VA
🎭 Wednesday, October 29 – Nov 1, Theatre Production: The Moors
Perfectly timed for spooky season, Randolph-Macon’s Theatre Department presents The Moors by Jen Silverman—a gothic dark comedy about love, power, and desperation on the bleak English moors. Quirky, haunting, and sharply funny, this production blends eerie atmosphere with biting humor.
📅 Oct 29 - Feb 1 | ⏰ 7:30–9 PM
📍 Randolph-Macon College Theatre
💵 Tickets: Free for RMC students/faculty/staff | $10 general admission (+ fee)
🔗 Reserve your spot
⚠️ Mature content: This show contains simulated acts of violence and sexuality. Ages 18+ only.
🎨 Thursday, October 30 – Creating Calm: Art Therapy Workshop
Unwind and explore creativity with expressive art therapy at the Montpelier Center. Perfect for managing stress with the healing power of art.
📅 Thursday, October 30 | ⏰ 6–8:30 PM
📍 Montpelier Center for the Arts
💵 $45/session | 🔗 Register here
🍭 Friday, October 31 – Candypalooza Lane
End October on a sweet note at Candypalooza Lane—a fun, family-friendly trunk-or-treat hosted by New Community Church. 🎃 Bring your costumes, candy bags, and big smiles to the paved parking lot beside Caravati’s Architectural Salvage for music, treats, and community fun. It’s the perfect way to celebrate Halloween in the Center of the Universe!
📅 Friday, October 31 | ⏰ 5–8 PM
📍 Caravati’s Architectural Salvage, 201 England St, Ashland
🍬 Friday, October 31 – Trunk or Treat at Local Christian Church
Join us for a safe and sweet evening of community fun at Local Christian Church’s Trunk or Treat! 🎃 Costumes, candy, and plenty of neighborly smiles will fill the church office parking lot for families of all ages.
📅 Friday, October 31 | ⏰ 5–8 PM
📍 112 England St A, Ashland, VA
☎️ 804-814-7196