Spooky Season in Charlottesville: The Best Halloween Events and Activities for Everyone

Visit Poe's Room at the University of Virginia

Did you know Edgar Allan Poe once called Charlottesville home? The American writer and poet attended UVA for about 10 months in 1826. Self-guided tours of his room on UVA Grounds are available year-round, though foot traffic picks up around Halloween, thanks to Poe’s flair for gothic and supernatural writing.

Escape 'The Raven Room' at Unlocked History

For an extra spooky night out, head to Unlocked History Escape Rooms for a history-themed adventure! 'The Raven Room' challenges teams of three to seven players to locate Poe, who has gone missing during his first year at UVA. The escape room is filled with puzzles, jump scares, and takes about an hour to complete.

Dare to Venture Out on a Ghost Walk

Virginia is a state steeped in mystery and folk lore. Head to Albemarle Ciderworks on Oct. 30th and experience the gruesome tales North Garden has kept secret for over 30 years! Bent Theatre offers a night of terrible tales, promising to capture your imagination and inspire the mind. The 8PM and 8:20PM candlelit walking ghost tours are suitable for children and teenagers. Tours from 8:40PM onwards have been created for mature audiences.

Pint-sized heroes, ghosts, and the like will descend on the University of Virginia for the annual “Trick-or-Treating on the Lawn” celebration on October 31st! This longtime tradition established by students in the late 1980s is open to children and families from the local community. Residents and members of approximately 70 student groups and organizations will be stationed in each of the 54 Lawn rooms as well as the West Range to give out treats.

Doggie Howl-O-Ween on the Downtown Mall

Head to the pedestrian Downtown Mall on Friday, Oct. 24th at 5PM for trick or treating with your dog (for dog treats instead of candy), hosted by Pawprints Boutique. There will be a costume parade at 6:30PM starting from the Pavilion with a contest and prizes at Pawprints Boutique afterwards. Lots of treats, prizes, raffles and fun, including a photographer, sketch artist, and face painters! Suggested donation of $15 goes to the Charlottesville-Albemarle SPCA.

SPCA Fall Festival (Costume Contest and Doggie Pie-Eating Contest)

Bring the whole family for a fun-filled day to support the lifesaving work of the Charlottesville-Albemarle SPCA on October 18th. Admission is free, with activities, food, and entertainment for everyone. Enjoy 30+ local vendors, trick-or-treating, SuperFun Inflatables, and adoptable animals on-site. Fall Fest will also feature an onsite raffle, a dog costume contest, and the hilarious dog pie-eating contest! Adoptions are sponsored the whole weekend thanks to Subaru Loves Pets!

Keswick Vineyards Howl-O-Ween Puppy Parade

Details Coming Soon

Virginia Discovery Museum's Boo Bash

Head to the Virginia Discovery Museum on the Downtown Mall for their annual family-friendly Halloween carnival on October 23rd or 24th! The Boo Bash is perfect for young children aged 2- to 8-years-old. Dress up in your most creative costumes and enjoy frighteningly fun carnival games, activities, and crafts like concocting potions, ooey-gooey glow-in-the-dark slime, and more! 👉 Reserve Your Tickets Here

Halloween Hangout at Dairy Market

Stop by the Dairy Market on October 24th for a free, family-friendly evening of Halloween fun! Enjoy live music, trick-or-treating, a dog costume contest, games, and face painting. Kids can get creative with pumpkin painting and crafts while supplies last. 👉 Reserve FREE Tickets Here

Boo-Thru at The Shops at Stonefield

Ghouls, goblins, and witches too -- celebrate Halloween on October 26th from 2-4PM at The Shops at Stonefield! Local area sponsors will be on-site to hand out treats to your little boos and ghouls. Free to attend.

Jackfest

This family-friendly festival, hosted at Foxfield from 12-4PM on October 26th, is all about fun, community, and raising money to help families battling childhood cancer. ​JackFest has a wide variety of fun activities including kid's running races, bounce houses, games, truck/emergency vehicle touch, arts and crafts, cartoon portraits, food trucks, and local wine/beer for adults!

YMCA Halloween Hustle (10K Run & 2 Mile Walk)

Celebrate Halloween and support a good cause with the YMCA Gatorade Halloween Hustle 10k Run & 2 Mile Family Walk on October 25th. This family-friendly event is a great way to get some exercise, enjoy the fall weather, and give back to the community. Participants are encouraged to wear their favorite Halloween costumes, and there will be plenty of treats and surprises along the way!

Halloween at The Birdcage!

Head to The Birdcage on October 31st from 5-10PM for a spooky good family-friendly time! Free to attend, there will be a kid candy swap, costume contest, haunted house, face-painting, fun music, and spooky vibes. 👉 RSVP Here

Hallowine at Southwest Mountains Vineyards

Head to Southwest Mountains Vineyards on October 25th for a full day of fall fun! From 11AM-5:30PM, enjoy live music, food trucks, apple bobbing, a costume contest, and more. Stick around longer for Hallowine Late Night from 6-9PM, featuring live music, Sweet Jane's Kitchen, and a Spooky Wine Walk (ticketed) through the vineyards, which includes four spooky wine drink stops along the way!

Poloween at King Family Vineyards

Sunday Polo just got a bit spookier! Head out to King Family Vineyards on Sunday, October 26th for Poloween, their annual family-friendly Halloween celebration at Sunday Polo! Enjoy a day full of excitement with costume contests, tailgate competitions, and more spooky fun as they wrap up their 2025 season.

Read Between the Wines Book Club

On October 30th, head to Commerce Street Books (located in The Doyle Hotel) for the first meeting of Read Between the Wines, a book club co-hosted by Samantha Jones and presented in partnership with the Monticello Wine Trail. Their October pairing features Dearest by Jacquie Walters, a richly layered novel exploring love, memory, and belonging, beautifully complemented by the expressive Mourvèdre from Stinson Vineyards.

Chisholm Vineyard's Halloween Party

Stop by Chisholm Vineyards on October 31st from 6-9PM for a special, spooky edition of their Friday Sunset Soirée! Live music from Vinyl DJ Ryan Wood, food truck, 100% estate wine, and Blue Ridge Mountain sunset view. Wear a costume and join in the fun! No ticket or fee to enter.

Nocturne Halloween Ball at Merrie Mill Farm & Winery

Elegant darkness. Divine decadence. Come dressed to kill! Head to Merrie Mill Farm & Vineyard on November 1st for a midnight masquerade with tech, house, and soul until 1AM. Tarot readings, portraits, and firelight set the scene for a Halloween Ball like no other.⁠ 👉 Get Your Tickets Here

Area 51: Halloween Invasion - UP on the Roof

This Halloween, Charlottesville's own Whistlepig Band is touching down to rock UP on the Rooftop from 6-10PM. No abductions; just out-of-this-world cocktails, space-worthy snacks, and a sound that’s nothing short of stellar. The party will also feature a costume contest, with prizes for Best Alien-Inspired Costume and Best Overall Costume.

Sounds of Love: THE DARK SIDE [Halloween Rave] - Common House

details coming soon.

Fantasy Festival Afterparty - IX Art Park

details coming soon.

Disenchantment Under the Sea at Visible Records

details coming soon.