Carytown doesn’t just celebrate Halloween — it becomes Halloween. Every October, the vibrant mile-long stretch of boutiques, restaurants, and murals lights up with cobwebs, carved pumpkins, and endless creativity. Known for its quirky energy and community spirit, Carytown turns spooky season into an immersive experience for locals and visitors alike. Whether you’re a family with kids, a college student looking for nightlife, or a couple planning a cozy autumn date, Carytown has a Halloween event for you.
1. Trick-or-Treat on Cary Street
No list of Halloween events in Carytown is complete without the neighborhood’s signature Trick-or-Treat on Cary Street, a long-standing tradition that draws hundreds of families every year. Shops along the strip open their doors to costumed kids and candy seekers, while business owners compete for the best-decorated storefronts.
The event usually takes place the weekend before Halloween, and you’ll see everything from miniature superheroes to toddlers dressed as tiny pumpkins. Local favorites like World of Mirth and Chop Suey Books often go all-out with elaborate decorations and generous candy bowls. For parents, it’s a safe, walkable way to experience the heart of Carytown while their kids revel in the sugar rush.
2. The Byrd Theatre’s Haunted Movie Marathon
Carytown’s legendary Byrd Theatre turns into a cinematic time capsule every October. Built in 1928, the theatre’s ornate architecture sets the perfect eerie mood for classic horror films. The annual Haunted Movie Marathon features everything from black-and-white classics like Dracula and Psycho to modern thrillers and family favorites like Hocus Pocus.
What makes the experience even more atmospheric is the Byrd’s original Wurlitzer organ, which still plays before select screenings. Sit back with popcorn, listen to the haunting pre-show melody, and feel like you’ve stepped into another era — one where ghosts might just be sitting in the row behind you.
3. The Carytown Monster Crawl
When night falls, Carytown’s adults trade candy for cocktails. The Carytown Monster Crawl has become one of Richmond’s liveliest bar events, uniting locals in wild costumes and themed drinks. Venues like The Jasper, Can Can Brasserie, and Citizen Burger Bar each host their own contests and specials. Expect eerie lighting, pumpkin-spice martinis, and maybe even a live DJ disguised as Dracula.
It’s not uncommon to see entire friend groups dressed as movie casts or clever pop-culture parodies. If you plan to join, come early — parking fills fast, and lines outside The Jasper can get long. Remember, the unofficial rule of Carytown Halloween: the more creative your costume, the more photos you’ll end up in.
4. Pet Costume Parade
Carytown loves its pets as much as its coffee, and Halloween brings out the cutest side of the community. The Annual Pet Costume Parade, typically held near Carytown Burgers & Fries, features dozens of dogs (and occasional cats) strutting their stuff in themed costumes. You’ll spot dachshunds dressed as hot dogs, golden retrievers in superhero capes, and even a few brave owners matching their pets.
The event raises donations for local animal shelters, so every wagging tail supports a good cause. It’s equal parts heartwarming and hilarious — and a favorite photo op for every passerby.
5. Fall Pop-Up Markets and Artisan Events
Beyond the big Halloween celebrations, Carytown hosts a rotating lineup of autumn pop-up markets throughout October. The Carytown Farmers Market, Made in RVA Holiday Market, and smaller art pop-ups in front of local boutiques feature hand-poured candles, spooky crafts, and vintage finds.
Many artisans design limited-edition Halloween items — think skull-themed ceramics, local honey with pumpkin labels, or horror-movie-inspired prints. These markets are ideal for anyone who prefers their Halloween shopping local and handmade.
6. Sweet Treats and Seasonal Specials
If you’re the type who celebrates Halloween through your taste buds, Carytown delivers. For the Love of Chocolate stocks imported candies and ghost-shaped truffles that vanish fast. Sugar & Twine rolls out pumpkin-spice croissants, and Bev’s Homemade Ice Cream launches its fall flavors — expect cinnamon apple, maple pecan, and the occasional “witch’s brew” special.
Meanwhile, The Daily Kitchen & Bar and Jardin update their menus with autumn cocktails like spiced pear margaritas and blood-orange spritzers. Carytown’s culinary scene thrives on creativity, and Halloween is its most flavorful month.
7. Late-Night Haunts and Local Legends
For those who love the darker side of Halloween, local storytellers host “Ghost Walks” exploring Carytown’s historic corners and whispered folklore. Some tours start near The Byrd Theatre, weaving through alleys and old buildings rumored to be haunted by former residents.
While there’s no guarantee of paranormal encounters, the candle-lit atmosphere and eerie stories make it a thrill for history buffs and ghost enthusiasts alike. The mix of fact, fiction, and RVA folklore keeps guests coming back year after year.
Conclusion
Halloween in Carytown isn’t just a single event — it’s a season. The neighborhood’s blend of local businesses, creativity, and community spirit turns October into a celebration that feels both intimate and electric. Whether you’re carving pumpkins at home or dancing in costume under neon lights, Carytown invites you to join the fun and create your own spooky traditions.
So this Halloween, head to Richmond’s most colorful neighborhood. Wander the mile, sip something seasonal, and see why Carytown has earned its reputation as the heart of RVA’s Halloween magic.
