Oregon Hill Halloween Parade 2025: Twenty Years of Beautiful Chaos

by | Nov 3, 2025 | COMMUNITY, HALLOWEEK

For two decades, the Oregon Hill Halloween Parade has been proof that community doesn’t need permission to exist. Every year, thousands of neighbors and artists spill into the streets with puppets, lanterns, hand-made costumes and signs, a homespun procession that’s equal parts protest, pageant, and block party. There’s no corporate sponsor, no barricades, just the rhythm of drums and laughter echoing through one of the city’s oldest neighborhoods.

Photographer Michael Simon captures what makes this night matter: the faces in the crowd, the blur of movement, the joy of recognizing yourself in the chaos. In his black-and-white shots, the parade feels timeless, where Richmond’s DIY spirit takes physical form. It’s messy, loud, inclusive, and deeply local. For a few hours each Halloween, Oregon Hill becomes a reminder that our best traditions aren’t built from budgets or branding, but from people showing up, together.

We would like to thank Lily Lamberta and All The Saints Theater Company for their continued efforts in keeping this grassroots tradition alive. Donations are still being accepted to ensure the parade continues for years to come, supporting the artists, neighbors, and volunteers who make it possible. To donate, you can go HERE.

Also, you can read The Richmonders excellent piece on the behind the scenes process HERE.


Support RVA Magazine. Support Independent Media in Richmond.

At a time when media ownership is increasingly concentrated among corporations and the wealthy, RVA Magazine has remained one of Richmond’s few independent voices. Since 2005, the magazine has provided grassroots coverage of the city’s artists, musicians, and communities, documenting the culture that defines Richmond beyond the headlines.

But we can’t do this without you. A small donation, even as little as $2, one-time or recurring, helps us continue to produce honest, local coverage free from outside interference. Every dollar makes a difference. Your support keeps us going and keeps RVA’s creative spirit alive. Thank you for standing with independent media. DONATE HERE.

We’ve got merch HERE
Subscribe to the Substack HERE
And Reddit HERE
And YouTube HERE

R. Anthony Harris

R. Anthony Harris

In 2005, I created RVA Magazine, and I'm still at the helm as its publisher. From day one, it’s been about pushing the “RVA” identity, celebrating the raw creativity and grit of this city. Along the way, we’ve hosted events, published stacks of issues, and, most importantly, connected with a hell of a lot of remarkable people who make this place what it is. Catch me at @majormajor____




more in community

Thousands of Lanterns to Light Up Dorey Park

The Water Lantern Festival returns to the Richmond area on Saturday, August 22, bringing thousands of glowing lanterns to the water, along with live music, food and what looks like a pretty laid-back way to spend a summer evening. You get a lantern and make it your...

Richmond’s Famous Romantix Mural Gets a New Chapter

For a decade, the mural outside the Romantix adult store, formerly Taboo, on Midlothian Turnpike has been one of Richmond's most debated pieces of public art. Now it's gone, replaced by a new collaboration between tattoo artist and muralist Jesse Smith and Miami-based...

As Funding Shrinks, Richmond’s Safety Net Is Full

She decided to finally leave. Maybe it was after years of abuse, or after one violent night too many. Maybe it was the first time she truly believed that if she stayed, she might not survive. Whatever brought her to that moment, making the call took courage.  On...

Seeing Richmond Through Their Eyes

Editor's Note: Writers Block is an occasional series featuring personal essays, reflections, and creative nonfiction from Richmond-area writers. In Seeing Richmond Through Their Eyes, Gabriella Ryan shares how a month spent showing her Italian cousins around Richmond...

Can Firehouse Put Richmond on the National Theatre Map?

In the electric and perpetually sincere terrain of Richmond’s theatre culture, there are institutions that do more than merely reside, they lead. They serve as a measure of our city's potential beyond its natural aspirations. I've witnessed Firehouse Theatre inhabit...

Photos | Warriors in Bloom at Agecroft Hall

For one weekend, Agecroft Hall stopped being a museum and became a kingdom.  What began as a fundraiser to help launch Richmond's first Renaissance Faire has grown into a destination of its own. Warriors in Bloom, created by the folks at Virago Alley, returned with...

Dispatch from the Lewis Ginter Picket Line

An on-the-ground account of the strike that prompted Jesse Welles and Graham Nash to cancel their Richmond performances. Tensions escalated as Jesse Welles called off his performance at Lewis Ginter Botanical Garden yesterday amid an ongoing union fight for higher...