Ashland Halloween is 31 Days of Spooktacular Fun, Safety, and Community Spirit

If you’ve ever strolled through Ashland in October, you know there’s something truly magical about Halloween in the Center of the Universe. From the fiery autumn leaves glowing along the upcoming Fall Line Trail to the laughter of costumed children skipping across historic sidewalks, Ashland has long been the heartbeat of Halloween in Central Virginia. This year, thanks to the Downtown Ashland Association (DAA), neighbors, sponsors, and volunteers, the Halloween season is shaping up to be not just spooktacular but also safer than ever.

Nicole Dillon of Breemar Flower Farm with her festive family during Halloween in Ashland.

For decades, Ashland’s charming train town setting has drawn thousands of families to its picture-perfect neighborhoods for trick-or-treating. “Ashland Halloween is hands down one of my favorite nights of the year—the spooky trains rumbling by, candy shoots on every porch, and the incredible decorations that bring our community to life,” shares Nicole Dillon of Breemar Flower Farm. “I’m thrilled to sponsor this celebration and be part of a night where memories are made, neighbors come together, and the magic of Ashland truly shines!” Realtor Nate Simon echoed the sentiment, saying, “My family has enjoyed Ashland Halloween for years, and it has become one of our favorite yearly traditions. It is so much fun with everyone making memories, and the streets are filled with amazing costumes and thoughtful decorations. That incredible energy is what inspired me to sponsor this year’s celebration.”

But with crowds gathering near the train tracks, rail-side restaurants, and downtown shopping, the need for safety has grown just as quickly as the piles of candy on every porch. Downtown Ashland Association is stepping up with a creative plan: fundraising for candy, amplifying 31 days of family-friendly events, promoting train safety, and giving gifts to homes that join the official Trick-or-Treat Map and Scavenger Hunt—all designed to keep Ashland’s Halloween on track and away from the trains.

Songs from the Center of the Universe Concert at historic Hanover Arts and Activities Center

“With railroads crossing our state and traveling through our communities, rail safety in the Commonwealth is a priority for VPRA,” added DJ Stadtler, Executive Director of Virginia Passenger Rail Authority. “Whether you are traveling on board one of our trains or crossing a railroad track, it is important to remember that if you see a track, you should expect a train. Practicing safe behaviors whenever you are near a track, in a station, or on a train can save your life.”

That focus on safety is matched with a big helping of neighborly generosity. At the Songs from the Center of the Universe Concert on Saturday, September 27, local musicians and Ashland Song Contest winners will take the porch stage at the Hanover Arts and Activities Center while vendors line the lawn. Instead of paying booth fees, each vendor will donate a 300-piece bag of candy—directly supporting Ashland homes most overrun by trick-or-treaters. Amtrak Virginia will also be there with train safety tips, giveaways, and even the chance to win free tickets.

DAA’s clever candy plan doesn’t stop there. Those bags of donated candy will be distributed to Ashland residents on October 25 at the Off the Rails Craft Beer Festival: Brews, Boos, and BBQ! Neighbors who show proof of residence can collect free candy, with priority for homes on Center Street and Railroad Avenue. Families are encouraged to linger on the historic lawn, enjoying craft beer, barbecue, artisan shopping, and live music from Buckville Hootenanny. “At Islamorada Fish Company, we believe that community events like these play a vital role in bringing people together and creating lasting memories for families and children.” said Islamorada Fish Company Restaurant inside Bass Pro Shops. “By sponsoring this event, we aim to contribute positively to these efforts and demonstrate our commitment to the well-being and happiness of our local community."

Of course, Ashland Halloween isn’t just one night—it’s a month-long festival of pumpkins, costumes, and community connection. From October 1 through 31, visitors can browse a full calendar of events at AshlandHalloween.com. With concerts, haunted history tours, shopping specials, and more, the celebration has something spooky and sweet for everyone—without cramming it all into one night. 

Ashland Halloween scavenger hunt prize winners with their glowing rewards.

Generosity is also glowing—literally—thanks to DAA’s giveaways. Ashland Halloween yard signs will be available at the Ashland Feed Store starting September 29 for any local home to keep and display, with 200 up for grabs. The first six homes to sign up for the Trick-or-Treat Scavenger Hunt will also receive glow-in-the-dark wands to help light the way for children and guide them safely toward candy stops away from the tracks.

RED VEIN Haunt is adding thrills to the season with a raffle for four Fast Passes to their legendary haunted attraction at Hanover Vegetable Farm. With movie-quality sets, live actors, and immersive scares, RED VEIN is not for the faint of heart. Raffle tickets are just $10, with proceeds supporting DAA’s nonprofit mission.

Randolph-Macon student volunteering during Halloween in Ashland

Adding to the spirit of giving, Randolph-Macon College’s SERVE Program is rallying student volunteers to support Ashland residents on Halloween night. These students will help neighbors hand out candy, offer homeowners a well-deserved break from the steady stream of trick-or-treaters, and delight children with light-up games and sticker prizes. It’s another reminder that Ashland’s magic doesn’t just come from candy and costumes—it comes from neighbors, young and old, working together to keep traditions bright and community connections strong.

Even local businesses are stepping forward to keep the magic alive. Minute Man Press of Ashland is printing postcards to ensure every Ashland home knows about these efforts and is also producing bright orange Ashland Halloween apparel to help families stand out in the festive downtown crowds. “Our decision to participate as a sponsor stems from our deep dedication to supporting the community,” Bass Pro Shops shared, “Fostering a safe and enjoyable environment for children, and promoting fun and festive activities for all attendees.”

Embrace Treatment Foster Care emphasized the deeper meaning behind the festivities. “With every trick-or-treat that is handed out, please remember the importance of community—it brings joy, safety, and a sense of belonging,” they said. “Please reach out if you are interested in learning more about fostering or if you or your business would like to work alongside Embrace to help spread the word on the need for foster parents.”

This October, Ashland proves once again why it’s called the Center of the Universe. By blending creativity, community spirit, and just the right amount of spooky fun, Downtown Ashland Association is making sure Halloween is more magical, memorable, and safe than ever before. From candy-filled concerts to pumpkin-lit porches, neighbors and visitors alike can find everything they need for a spooktacular October in downtown Ashland at AshlandHalloween.com