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.
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.
Starting October 17th, the Albemarle Charlottesville Historical Society will be offering a tour through Maplewood Cemetery, the city's oldest public burying ground, every Saturday at 4PM. This guided walking tour is a chance to discover the stories of the people who shaped the area, from prominent figures to everyday residents.
Pint-sized heroes, ghosts, and the like will descend on the University of Virginia for the annual “Trick-or-Treating on the Lawn” celebration. The 2026 date will be announced in September.
This longtime tradition was established by students in the late 1980s! 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.
Head to the pedestrian Downtown Mall on Saturday, October 24th from 4-8:30PM for trick or treating with your dog (for dog treats instead of candy), hosted by Pawprints Boutique. There will be a costume parade 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.
Bring the whole family to IX Art Park on Sunday, October 4th from 11AM-3PM for a fun-filled day to support the lifesaving work of the Charlottesville-Albemarle SPCA! Admission is free, with kid, canine, and adult activities that celebrate both the fun and the mission behind animal sheltering. Fall Fest will feature an onsite raffle, a dog costume contest, flash tattoos and the hilarious dog pie-eating contest! Adoptions are sponsored the whole weekend thanks to Piedmont Tire Company!
This family-friendly festival, hosted at Foxfield from 12-4PM on Sunday, October 18th, 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!
Head to the Virginia Discovery Museum on the Downtown Mall for their annual family-friendly Halloween carnival on October 29th and 30th, 2026. 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!
Head to Albemarle Ciderworks on Saturday, October 24th for an opportunity to star gaze with guidance from the UVA Astronomy Department! There will be telescope observation using Celestron, Dobsonian and UniStellar telescopes, hands-on astronomy activities, a portable planetarium, and (for adults) cider tastings.
Stop by the Dairy Market on Saturday, 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.
Head to the Virginia Discovery Museum on the Downtown Mall for their annual family-friendly Halloween carnival on October 29th and 30th, 2026. 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!
Celebrate Halloween and support a good cause with the YMCA Gatorade Halloween Hustle 10k Run & 2 Mile Family Walk on Saturday, October 31st. 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!
Venture to Southwest Mountains Vineyards on Saturday, October 24th for a haunting journey of wine and fright in the vineyard after dark. This spooky wine walk includes four wine drink stops along a haunted path, with scary elements and surprised lurking along the way. Wine walks are ticketed and start at 7PM -- come earlier and enjoy other activities such as food trucks and live music.
Sunday Polo just got a bit spookier! Head out to King Family Vineyards on Sunday, October 25th for Poloween, their annual family-friendly Halloween celebration at Sunday Polo! Enjoy a day full of excitement with costume contests, tailgate competitions, and spooky fun as they wrap up their 2026 season.
On Sunday, October 25th, head to Chiswell Farm & Winery to celebrate Halloween and support a local nonprofit! Bring your best witch costume to their 3PM contest and enjoy some hauntingly live music while you're there.
Halloween is taking over Eastwood Farm and Winery! Put on your best costume and head out on Saturday, October 31st for an evening of swing dancing, live music, wine, and Halloween fun. Swing Cville will kick things off with a swing dance lesson at 4 PM, followed by live music from Zuzu’s Hot 5 from 5–8 PM. Costumes are highly encouraged.
Head to Glass House on Saturday, October 31st for a groovy night of Halloween fun inside their tropical oasis. Doctor Rhythm (featuring King Gypsy)'s collection of R&B, Blues, Soul, and Reggae tunes will have everyone doing the Monster Mash and Zombie Conga Line! Jones Catering will be onsite and costumes are encouraged!
Head to Potter's Craft Cider on Saturday, October 31st for a night of spooky fun, live music, and seasonal cider! Their Halloween bash will feature a high-energy performance from local party-rock legends The Falsies. Expect outrageous costumes, over-the-top antics, and a setlist packed with crowd favorites and Halloween flair.
Elegant darkness. Divine decadence. Come dressed to haunt, enchant, or simply turn heads. Head to Merrie Mill Farm & Vineyard on Saturday, October 31st for a midnight masquerade with lounges, bars, and of course a blistering dance floor. House DJs will be spinning inside the eclectic Merrie Mill Manor until 1AM!
On Saturday, October 31st, head to The Jefferson Theater for a special Halloween edition of Gasolina (18+) featuring nonstop reggaeton and latin-music. Come dressed in costume and ready to party!
When the outdoor festivities end on October 31st, the realm opens inside The Looking Glass at 9PM for a neon-soaked, adult-only night of DJs, performers, art, and celestial libations. Expect a high-energy dance floor, immersive visuals, and costumed creatures of every kind. Costumes are highly encouraged - come as your boldest alter ego!
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