Best Festivals in the Bluegrass in October

Fall foliage may come later to Kentucky's Bluegrass Region than it does to our neighbors to the North, but fall festivals arrive right on time.

If you thought September brought a bonanza of celebrations, October is just as generous, with festivals focused on food (burgoo, anyone?); art & culture; a Civil War battle; millstones, and movie monsters.

So, come visit the Bluegrass Region in October and get a side of festivals along with the main course of horses and bourbon.

Where Can I Find the Best Festivals in the Bluegrass Region in October?

October 2 & 3 – Perryville Commemoration: Troops & Tradition – Perryville, Boyle County

The Battle of Perryville may not have the name recognition of Bull Run, Shiloh or Gettysburg, but Abraham Lincoln called it one of the most significant battles of the Civil War. Why? A Confederate victory could have cut off the Union supply lines along the Ohio River, preventing federal troops fighting in the Deep South from receiving arms and ammunition.

While the battle is described as a tactical victory for the South, the relentless pressure from the Union Army forced the withdrawal of the Confederate Army in Kentucky.

Every year Boyle County remembers the fiercely contested Battle of Perryville. This year will see re-enactors and a memorial service, but there will also be more family-friendly ways to enjoy this free remembrance ceremony.

There will be parades, living history demonstrations, interpretive panels, live music, food, arts & crafts vendors.....even a Kids' Corner.

October 3 – Millstone Festival – Richmond, Madison County

Richmond has one of the region's most unusual festivals when every October it honors the large millstones that are symbols of the rich history of the milling industry in Madison County.

The full day of music, food, history and fun will take place in and around Millstone Park in downtown Richmond from 11:00 a.m. to 8:00 p.m.

After admiring the collection of more than 40 historic millstones (ranging in weight from 200 pounds to 4,000 pounds) scattered throughout the park, wander Main Street to check out the day's special deals and bargains at local shops and restaurants.

Craft, food, beer and wine vendors will be there throughout the day as will a petting zoo and the popular Millstone Cruise-in, a collection of classic cars.

In the afternoon, a musical line-up will feature the Jenkins Twins, Bourbon Revival and Rhythm Phoenix.

October 3 – Wilmore Arts & Crafts Festival – Wilmore, Jessamine County

Wilmore is a nostalgic college town most of the year, but every fall its Main Street and Downtown Green come alive with the excitement of a county arts & crafts fair.

This year's event will feature more than 60 local and regional vendors offering juried art and handcrafted artisan pieces including pottery, woodwork, jewelry, candles, soaps and holiday wreaths.

Shopping is always better with a soundtrack and some refreshment, so there will be live musical performances and a variety of food trucks alongside local restaurants.

October 3 – Bourbon on the Banks – Frankfort, Franklin County

If it's October, it means Bourbon on the Banks in Kentucky's capital – a chance to bring distillers and lovers of bourbon together to celebrate the commonwealth's signature drink.

More than 70 distilleries (along with select wineries, breweries and craft spirits) will be set up in River View Park for tastings and talks.

To go along with the spirits, there will be live music from regional artists, food vendors and shopping.

Hours are from 12 noon (special access) to 6:00 p.m. with general admission beginning at 2:00 p.m. Tickets are available through Eventbrite, and you must be 21 to attend (photo ID required.)

October 10 – Wilderness Road Music Fest – Stanford, Lincoln County

The Road will be alive with the sound of music for a memorable night in Lincoln County. The Road is the Wilderness Road – along which thousands of settlers poured into Kentucky in the 18th and 19th centuries – and the music is the country and bluegrass that has come to be associated with the annual Wilderness Road Music Fest.

This year, J.D. Shelburne and his Nashville Band will take the stage at the Lincoln County Courthouse for a free concert to wrap up the 2026 Fest.

Bring your lawn chair and get ready to listen to Shelburne, widely known for his debut album "Straight From Kentucky."

October 16-18 – Burgoo Festival – Lawrenceburg, Anderson County

Anderson County residents love their burgoo – so much that every October they take an entire weekend to celebrate the traditional slow-cooked stew that was originated by pioneers more than 200 years ago and refined over the succeeding two centuries (that means chicken and beef have replaced possum and squirrel as the main sources of protein).

Burgoo masters from the county and beyond gather in Century Bank Park to stir their stew, serve samples and swap stories with the throngs who come to savor a dish that just can't be found in Vermont or California.

There will also be carnival rides, craft vendors, community booth displays, and live music (this year Josh Pack, known as "the Kentucky Elvis," & the Fever).

All well and good, but on this occasion the King takes a back seat to the burgoo. We think he'd be okay with that.

October 17 & 18 – Kentucky Guild of Artists and Craftsmen Fall Art Market – Berea, Madison County

If you are a serious collector – or aspire to be – you can't miss this annual fall event in Kentucky's Folk Arts and Crafts Capital.

For 51 years, Berea, nestled in the Cumberland Mountains, has hosted a Fall Art Market, beginning with its origins at the Indian Fort Theater in the Berea College Forest to its recent move to the Kentucky Artisan Center.

Over the two-day period, arts and crafts lovers can check out the works of skilled artists and artisans from across the commonwealth.

In addition to the art, there will be music and food (art in their own way, after all).

October 24 – Ginkgo Galore Festival – Wilmore, Jessamine County

In case you didn't know......Wilmore has been proclaimed America's official Ginkgo Capital, and we want to share our resident trees that began in China more than 270 million years ago.

So, join our mascot Goldie the Ginkgo for a day celebrating creativity and community.

The full day of activities features a 5K run/walk; live music; scavenger hunts, kids' games, storytelling, and an art contest with cash prizes for the winners.

Check Goldie's Facebook profile for frequent updates and join our 20 plus community partners for a golden day of arts, music and more.

October 25 – 31 – Breeders' Cup Festival – Lexington, Fayette County

During the last week of October, horse lovers from around the world will converge on Lexington for the Breeders' Cup World Championships which will be held for the fourth time in 11 years at Keeneland Racecourse.

However, as with previous Breeders' Cups, the city will welcome racing fans with a full week of activities guaranteed to have them celebrating even when the Thoroughbreds aren't running.

The festival will kick off with an equine-themed family day on October 25th in downtown Gatton Park where horses and jockeys will be on hand for introductions and photos, and will continue with a week of music, food, art, and horse country culture that is sure to make everyone feel like an insider whether they have tickets to the Breeders' Cup race or not.

October 23 – 25 – ScareFest Weekend – Lexington, Fayette County

Get ready to have your wits scared out of you at this "spooktacular" event held at Central Bank Center/Rupp Arena in downtown Lexington.

Whether Freddy Krueger invades your nightmares; Jason Voorhees has turned you off lake swimming, or Michael Myers has convinced you to forego trick or treating on Halloween, you will have plenty of ghouls, ghosts and goblins to hob knob with at Kentucky's largest annual horror convention.

Expect to chat with celebrities; attend a film festival of independent horror films and attend a paranormal panel.

Come join some 30,000 other horror fans in Lexington for ScareFest.......if you dare.