Best September Festivals in the Bluegrass Region

Best September Festivals in the Bluegrass Region

Fall Festivals in the Bluegrass Region: September

Fall in the Bluegrass Region means football, foals, foliage and festivals — lots of them. As autumn nudges summer out with a gentle breeze, the festival season not-so-gently kicks into high gear, celebrating everything from horses to honey and heroes to heritage.

Come join us in the Bluegrass Region during our liveliest festival season.

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

September 5 & 6 — Daniel Boone Pioneer Festival

Winchester, Clark County

It only makes sense that one of the commonwealth's historical heroes is honored with his own festival. And that happens in Clark County every September with the Daniel Boone Pioneer Festival.

Over the festival's two days, locals and visitors will mingle in historic downtown Winchester to browse for handmade arts and crafts; sample the offerings from food vendors (although we can't promise you possum or squirrel stew); take part in a 5K walk/run; and groove to live music from the likes of 3 Men & a Banjo and the Conch Republic Band.

And who knows — you might even spot a coonskin cap or two among festival-goers.

September 11–13 — Best of the Bluegrass: Festival of the Horse

Georgetown, Scott County

Does three days of parades, live music, food vendors and family fun centered on the horse sound appealing? If so, be sure to be in downtown Georgetown for this year's 45th anniversary festival.

Downtown will be transformed with a craft beer garden, an amusement park, pop-up craft vendor booths, a Fireman's Chili Cookoff (on September 10 — talk about 5-alarm), and a musical stage for musicians from across the region.

While the bands have Bluegrass star power, it's the four-legged entertainers who steal this show. Make sure you're on hand for:

  • Colt & Filly Review Parade — Sept. 11 at 6:30 p.m.
  • Grand Parade of Horses — Sept. 12 at 5:00 p.m.
  • Blessing of the Animals and the Scott County Humane Society's Pet Parade — Sept. 13 at 1:30 p.m.

In honor of the 25th anniversary of 9/11/2001, there will be a special public remembrance ceremony on Sept. 11 at 3:45 p.m.

Free admission.

September 11–13 — Roots and Heritage Festival

Lexington, Fayette County

This cultural celebration in downtown Lexington has been drawing crowds for more than three decades and has been recognized regionally as a "Top 20 Event in the Southeast" by the Southeast Tourism Society.

Following this year's theme of "I Am Legacy," the Roots & Heritage Festival will offer a colorful parade (Sept. 12) featuring community groups, bands and dance teams, and live entertainment from local and regional musicians spread across the three days.

Two popular events — soul food tastings and a Marketplace with local and Black-owned businesses offering crafts, clothing and cultural goods — will again be on the festival schedule.

September 12 — Constitution Square Festival

Danville, Boyle County

Every year, Danville curates a full day of art, music, food, artisan demonstrations and community spirit, bringing to life one of the city's most historic sites.

Constitution Square, where the town was born in 1792, transforms into an open-air marketplace where for one day creativity trumps history.

Forty artists showcase their work in mediums such as painting, weaving, glassblowing, metal and woodworking, and as a bonus, many will offer demonstrations. You won't have to watch in silence, however, as local musicians will bring energy and a lively atmosphere to the surroundings.

Neither will you have to go hungry. Food trucks and local eateries — from Billy's BBQ to Tallulah Sweet Spot — will be on hand to satisfy your hunger pangs and quench your thirst.

Should you want to take home some of nature's bounty, the Boyle County Farmers' Market will be set up to dispense fresh produce, baked goods, locally made products and seasonal favorites.

Free admission.

September 11 & 12 — Stave Fest

Lawrenceburg, Anderson County

Stave Fest, an annual free festival in downtown Lawrenceburg, has, despite its name, nothing to do with bourbon (for the uninitiated, a stave is a strip of wood used in crafting a bourbon barrel).

This festival instead is all about community spirit and celebrating local arts and crafts, food and music. Held at two locations — downtown Lawrenceburg's Main Street and Century Bank Park — the highlights will be the first evening's recognition of local heroes (military and first responders) and the second night's concert by country music great and Kentucky native J.D. Shelburne.

In between, there will be a lot more music as well as food trucks and vendors. But if you want bourbon, you'll have to make a stop at Four Roses or Wild Turkey Distilleries, both located in Anderson County.

September 11–13 — Jessamine County Downtown Days

Nicholasville, Jessamine County

Vendors, delicious food and entertainment geared to all ages will be the hallmark of this weekend festival in downtown Nicholasville.

A BBQ competition? We've got one. Farm-to-table experiences? We've got that too. The nostalgia of old-time radio? Our local favorite KCAL Old Time Radio Show will be on hand to demonstrate why their performances are sellouts.

And if you've never tried Squonk's Joy Machine — don't ask, just come try it for yourself.

September 12 — Cynthiana Honey Festival

Cynthiana, Harrison County

Talk about a honey of a festival — this just may be the sweetest celebration in Kentucky.

This festival is not all about shopping, entertainment, food and fun, although there is plenty of that. It also has an educational component. Organized by the Licking Valley Honey Bee Society, the event honors the importance of honeybees as pollinators and supports local beekeeping.

But don't worry — there will be plenty of sweet treats such as the popular Honey Bake-Off, Honey Show, and, new to the festival this year, the Pollinator Parade.

The party starts at 10:00 a.m. and continues until 5:00 p.m. Free admission.

September 18 & 19 — Oktoberfest

Lexington, Fayette County

Bavaria comes to the Bluegrass when Germany's gift to the world arrives at Lexington's Christ the King Church for two days of rollicking das Vergnügen (German for fun).

The musical style may be different (although one of the participating bands is named the Schnitzels), but the food and drink are right out of the Old Country. There will be bratwursts, German potato salad, sauerkraut and apple strudel, as well as an assortment of German beers.

There will also be games of chance (yep, the Dunk Tank and Cake Wheel are back), an inflatable obstacle course, and sand and scratch art.

See for yourself what has made this one a standout for 30 years.

September 18–20 — Spoonbread Festival

Berea, Madison County

Just the word makes Kentuckians' mouths water. What could be tastier than a huge slab of this Southern favorite — a cross between cornbread and corn pudding with a rich, buttery flavor that has just the right amount of sweetness?

If just reading this makes you hungry, head for Berea and this month's annual Spoonbread Festival, which this year turns 30. That's a lot of spoons digging into a lot of spoonbread.

Over the weekend, visitors will have plenty of opportunity to add to the number — either at the famous Boone Tavern or from one of the local vendors providing their own take on it.

Spoonbread may be the star, but the supporting cast is pretty special as well, from the opening night Balloon Glow, where hot air balloons decorate the night sky, to the closing day's annual car show.

September 19 & 20 — Midway Fall Festival

Midway, Woodford County

For more than half a century, some of the commonwealth's finest artists and artisans have been bringing their wares to this railroad community in the middle of horse country.

The centerpiece of the festival is the bustling marketplace where collectors can find high-quality art ranging from pottery and quilts to paintings and one-of-a-kind jewelry.

If you can tear yourself away from the marketplace, there are demonstrations of the state's rich cultural heritage, mouth-watering foods from savory to sweet, live music and plenty of activities to keep the little ones occupied.

September 26 — Witches' Day Out

Cynthiana, Harrison County

The Halloween witches will be arriving a little early in Cynthiana this year to usher in the town's month of "unearthly" activities and attractions.

The Dead may Walk and the Skeletons may Rattle, but it's the Witches that will get things started, ably assisted by local vendors, food purveyors and entertainers.

For a truly spellbinding time, come dressed as your favorite Halloween character and spend the day (from 12 noon to 7:00 p.m.) engaged in themed shopping, entertainment, photo ops, eating and drinking (careful — is that an eyeball in your libation?) and plenty of surprises.

The witches promise this will be a fun way to kick off Cynthiana's spooky season.