Things to do in October

Discover the best things to do in Ashland, Virginia this September, from festivals and local events to dining and shopping.

Things to do in and near Ashland, Virginia in October

Gather, Celebrate, & Explore! Discover why we love Ashland, VA.
October is here, bringing crisp air, local events, and plenty to discover.

Ashland Farmer’s Market
Every Saturday May – October

The Stuff of Nightmares
October 3rd
Step into the darker side of Gothic literature at Scotchtown with chilling stories, mysterious characters, and costumed interpreters portraying some of the era’s most haunting authors. An evening of history, literature, and a little bit of fright awaits.

The State Fair of Virginia
September 25th–October 4th
Experience one of Virginia’s favorite fall traditions at the annual State Fair of Virginia. From thrilling rides and live entertainment to agricultural exhibits, competitions, animals, classic fair food, and more, there’s plenty to enjoy at The Meadow Event Park each fall.

Fall Wine Tasting
October 7th
More details coming soon

Ashland Berry Farm
October 1st-31st
When the sun goes down, Ashland Berry Farm transforms into Terror on the Farm. Brave four terrifying haunted attractions, including haunted woods, eerie trails, twisted illusions, and plenty of scares waiting around every corner.

The C&W Hanover Septic Gourds, Goblets, and Ghouls Festival
October 10th-11th
Celebrate the fall season with a weekend of festive fun at the Gourds, Goblets & Ghouls Festival. Just minutes from the Henry Clay Inn, this family-friendly event offers a great way to enjoy autumn in Hanover County with seasonal activities, local vendors, live entertainment, and more.

Ashland Harvest Run/Walk
October 17th
Celebrate the fall season at the annual Ashland Harvest Run. This community tradition brings runners and walkers together for a scenic race through Ashland, with crisp autumn air and plenty of hometown spirit along the way.

Richmond Symphony Chorus
October 18th
Experience an afternoon of powerful orchestral and choral music as the Richmond Symphony and Richmond Symphony Chorus take the stage at Randolph-Macon College. Led by Richard Robbins, this special performance brings the works of Copland, Britten, and Shaw to Ashland’s Blackwell Auditorium.

Ashland Fourth Fridays
October 23rd
Ashland Fourth Fridays feature shops open late, farm-to-table fresh fare, vendors, and free live concerts every fourth Friday from May to September in Downtown Ashland. Discover, dine, and delight in the rich tapestry of talents that make our town truly special every fourth Friday from March through October.

Monsters of Rock Halloween Party
October 26th
Get ready to rock this Halloween at Richmond Harley-Davidson’s Monsters of Rock Halloween Party. Enjoy an afternoon of live music, Halloween fun, and plenty of rock-and-roll energy at one of Ashland’s favorite motorcycle destinations.

Halloween Afternoon Tea
October 27th-28th
More information coming soon

Costume Lounge Party
October 31st
More information coming soon

Convenient lodging for your adventures

With its central location, The Henry Clay Inn is the perfect home base for exploring all of Ashland and the Greater Richmond Region. Book your stay at The Henry Clay Inn today, where charming guest rooms and a spacious porch welcome you for a relaxing, fun filled getaway in the heart of Ashland.

We look forward to seeing you!

Looking for more local fun this month?

See more of what makes Ashland shine—visit our calendar page for more things to do in and near Ashland, VA.

Share the love! Next time you come for a visit, take a photo and tag us @henryclayinn on Facebook or Instagram. We would love to see and hear about your experience with us.