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Upcoming events in Kentucky

168 listed. Page 4 of 7

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Sep 24–26, 2026 Liberty, KY

Casey County Apple Festival

Organizer VendorsMapUnclaimed

Board Chair, Ms Deva Hair, honored the board members during May's monthly meeting by presenting them with the Kentucky Colonel award. All thanks to Senator Brandon Storm and Representative Daniel Elliott for the hard work in getting these for everyone. The board members, as well as the committee members, all work hard year round to make the preparations for the festival every year. Honoring the board members as Kentucky Colonels is a way of saying thank you for a wonderful 50 years! The Casey County Apple Festival also received an award from the Senate and the House, recognizing the 50 years of having the festival. Thank you, Senator Storm and Representative Elliott for your continued support! We hope that 51 will be bigger and better (and dry)! Casey Coppage, Sue Atwood, Patricia Richardson, Deva Hair, Terri Scott, Jeff Lee, and Freddie Whited The Casey County Apple Festival is still...

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Sep 24–27, 2026 Downtown London, KY

World Chicken Festival

Organizer World Chicken FestivalUnclaimed

The World Chicken Festival runs Thursday, September 24 through Sunday, September 27, 2026, in downtown London, Kentucky, honoring the legacy of Colonel Harland Sanders. Festival hours run 5 to 11 pm Thursday and 10 am to 11 pm Friday, with Sunday closing at 5 pm. The event features the World's Largest Stainless Steel Skillet, which has served more than 120,000 fried chicken dinners, drawing over 30,000 visitors annually.

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Sep 26–27, 2026 Versailles, KY

Central Kentucky Paw Paw Festival

Organizer Wildside WineryUnclaimed

<p>Celebrate Kentucky’s most legendary native fruit — the paw paw.</p> <p>Widely known as the favorite fruit of the Sasquatch.</p> <p>Join us among the vines for a weekend of flavor, folklore, and hands-on exploration of this mysterious woodland delicacy. Known for its creamy, tropical taste and deep Appalachian roots, the paw paw is ripe for celebration — and we’re doing it Wildside-style.</p> <p>Rumor has it… when paw paws are in season, certain woodland creatures tend to wander a little closer to civilization.</p> <li>Sip our small-batch paw paw blends and signature Paw Paw Wine Slushee — available only during festival weekend.</li> <li>Learn how to identify, harvest, prepare, and enjoy paw paws.Seed tastings, fruit demos, native plant education, and more — led by folks who actually know the woods.</li>

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Sep 26–27, 2026 Paris, KY

Legends of Bourbon County Festival

Organizer Legends of Bourbon County FestivalUnclaimed

The Legends of Bourbon County Festival celebrates the racehorse Ruffian in downtown Paris, Kentucky, with a Fall Meet Event on September 26 and a Main Street Festival on September 27, running from noon to 7 pm. The festival includes a Thoroughbred Marketplace and a concert stage.

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Sep 26, 2026 Harrodsburg, KY

Shaker Village Harvest Fest

Organizer Shaker Village of Pleasant HillUnclaimed

Shaker Village of Pleasant Hill's Harvest Fest runs Saturday, September 26, and Sunday, September 27, 2026, from 10 am to 4 pm in Harrodsburg, Kentucky. Activities include a hayride, pumpkin painting, archery, craft demonstrations, a Harvest Market of handmade goods, and watching sorghum processing and apple cider pressing, plus live music, food trucks and an outdoor bar. General admission ranges from free for kids 5 and under to $20 for ages 13 to 61 at the door.

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Sep 26, 2026 Bowling Green, KY

Bowling Green International Festival

Organizer Bowling Green International Festival / Service One Credit UnionUnclaimed

Activities, contests, and events take place before & during the festival. Authentic foods, cultural displays, edutainment activities and merchandise. to the sponsors who help make the Bowling Green International Festival possible! Purchase advance tickets ($5) on Eventbrite for half the festival day price ($10). Foodie Discount Cards ($10) are also half price ($5) when reserved online. 12 and under are FREE and do not require a ticket. Show your EBT card at the gate for $2 admission. Follow our social media for flash discount specials. Admission $10 festival day ( Buy earlier online and save ) – Children 12 & under FREE. Show your EBT card at the gate for $2 admission. Stop by our Merchandise Booth for our Restaurant Discount Cards & shirts designed by local artists.

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Sep 27–28, 2026 Louisville, KY

Nunnlea Craft Fair

Organizer Nunnlea Craft FairUnclaimed

Louisville’s hidden gem for weddings, corporate events and special occasions. Experience the graciousness of an antebellum mansion in Louisville, Kentucky. Nunnlea provides a beautiful setting for your special event. Built in the 1850s, the house and its outbuildings are listed on the National Register of Historic Places. Nunnlea is located at 1940 S. Hurstbourne Parkway, convenient to I-64. Your out-of-town guests will have their choice of overnight accommodations in the area. Nunnlea has sponsored a craft show for the past fourteen years and our emphasis, as always, is on local and regional artists who make the quality crafts that are a part of the culture in Kentucky and Indiana. This has proved to be profitable philosophy for both the artist and the Beautification League. If you are interested in participating, we are interested in seeing your work. We are looking for a variety of...

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Oct 1–3, 2026 Greenup, KY

Greenup Old Fashion Days

Organizer Greenup Old Fashion Days CommitteeUnclaimed

Get ready to experience one of Greenup County’s most treasured traditions! The first week of October each year, downtown Greenup will once again come alive with the sights, sounds, and flavors of Old Fashion Days. For nearly 60 years, this beloved event has drawn families, friends, and visitors together to celebrate our heritage with heart.

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Oct 1–3, 2026 Paintsville, KY

Kentucky Apple Festival

Organizer Kentucky Apple FestivalUnclaimed

Get parade details, entry information, and application forms to be part of one of the Kentucky Apple Festival’s most celebrated traditions. Showcase your products at one of Eastern Kentucky’s most beloved festivals. Apply today to be a non-food vendor and reserve your space. Find pageant details, important dates, and application information for the Miss Apple Blossom Pageant and related events. Join us in downtown Paintsville for one of Eastern Kentucky’s most beloved annual celebrations. Held the first Saturday in October, the Kentucky Apple Festival has brought together community pride, family fun, local crafts, delicious food, and unforgettable entertainment since 1963. There’s nothing quite like autumn in Paintsville during the Kentucky Apple Festival. Enjoy delicious local food, handcrafted goods, live music, family-friendly fun, and the warm welcome of a community that knows how...

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Oct 2–3, 2026 Middlesboro, KY

Cumberland Mountain Fall Festival 2026

Organizer Cumberland Mountain Fall FestivalUnclaimed

Welcome to this year's 2026 Cumberland Mountain Fall Festival!! We are excited to be preparing for our annual event and are even more excited to see everyone return! We appreciate your patience this year as we have worked to bring together new board members who cannot wait to make this fall festival memorable for all!

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Deadline Sep 26, 2026

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Oct 2–4, 2026 Louisville, KY

St. James Court Art Show

Organizer St. James Court Art ShowUnclaimed

Free Admission. Rain or Shine. No pets allowed. Voted #1 “Best Fine Art and Design Show Of The Past Ten Years” 2010-2020 by Sunshine Artist Magazine in 2020 Named #3 “Best Fine Art and Design Show” in the country in 2026 by Sunshine Artist magazine! 2026 marks a major milestone for the St. James Court Art Show ; our 70th year . To honor this historic anniversary, we’re planning special moments and surprises throughout the entire year, not just during the Art Show weekend. Check back often for exciting announcements as we celebrate 70 years of t he St . James Court Art Show. The St. James Court Art Show is a juried fine arts and contemporary crafts show featuring over 600 artists from around the U.S. held among the country’s largest collection of Victorian homes in the heart of historic Old Louisville. This 4-square block, outdoor art show takes place annually on the first weekend of O...

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Oct 2, 2026 Falmouth, KY

Kentucky Wool Festival

Organizer Kentucky Wool FestivalUnclaimed

For nearly four decades the Kentucky Wool Festival has proudly supported our community and worked to uphold our mission of celebrating artisans and local heritage. We look to the future with excitement to continue to further our mission and better our event for our guests. The festival is undertaking a number of improvements and infrastructure investments. Recently we have repaved the grounds and expanded parking but there is more work to be done. Moving forward electrical and technology upgrades are needed and we will be partnering with a professional organization for parking. Each year we are confronted with increasing costs for putting on the festival. In order to achieve our future goals and maintain a safe and high quality experience for our guests the Kentucky Wool Festival will be increasing the cost of admission. 3 Day passes will be available for $30 at each local bank in Fal...

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Oct 3–4, 2026 Louisville, KY

Bowman Fest 2026

Organizer HB ProductionsUnclaimed

Get up close and walk through a C130 military plane. Enjoy the sites of historic planes on display, War birds, military planes, vehicles, helicopters and a vintage car show. Rides will be available in various planes and helicopters for an additional purchase. There is something for everyone at BowmanFest like local food trucks, a bar featuring Green River Bourbon, Bouncy Houses for the little ones... family fun for all! BEFORE WE GET STARTED, GET READY FOR TAKE OFF WITH THE IPA 5K ON THE RUNWAY! IPA 5K on the Runway kicks off the event and ends under the wing of a C130 Military Plane. The IPA (Independent Pilots Association) benefits the Reach for Kids a 501c3. Your sign up includes a medal, t-shirt and drink ticket, plus admission to BowmanFest.

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Deadline Oct 3, 2026

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Oct 3–4, 2026 Versailles, KY

26 Wildside Crush Festival

Organizer Charismatic MediaUnclaimed

The Wildside Crush Festival October 3 & 4 Wildside Winery | 5500 Troy Pike, Versailles, KY The Wildside Crush Festival is our annual grape harvest celebration — a two-day festival honoring the moment when grapes begin their transformation into wine. This is harvest season at Wildside, when the vineyard and winery are full of energy, beauty, and anticipation for the vintage to come. Spend the weekend surrounded by vines, autumn light, music, and the rhythm of winemaking in motion. What You’ll Experience A vibrant winery in the heart of harvest season Harvest-inspired wines and seasonal drinks Live music throughout the weekend (lineup announced closer to the event) Food vendors and local makers A cozy fall vineyard atmosphere A relaxed, family-friendly festival vibe Why The Crush Is Special “The Crush” marks the moment grapes begin their journey into wine — a season of transformation, craft, and promise. This festival invites guests to slow down, wander the vineyard, and be part of the story behind every bottle. Free to attend. Wine, food, and festival offerings available for purchase.

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Closed Sep 3, 2026

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Oct 3, 2026 Richmond, KY

Millstone Festival

Organizer City of Richmond, KYUnclaimed

The Millstone Festival is Richmond’s annual fall celebration, bringing together neighbors and visitors alike for a full day of music, food, history, and fun. Held in the heart of downtown and the historic Mill District, the festival showcases the best of Madison County with activities for all ages, from kids’ games to live performances and artisan vendors. On Saturday, October 3, from 11:00 a.m. to 8:00 p.m., Main Street will be alive with activity. Stroll through blocks of local vendors, explore handcrafted goods, enjoy food and spirits around the courthouse square, and take in live entertainment throughout the day. The festival is family-friendly, community-centered, and offers something for everyone. Cruise-In – Car enthusiasts won’t want to miss the classic car cruise-in, where polished chrome and vintage style line the street. It’s a chance to admire 1frmobiles from every era and...

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Oct 9, 2026 Olive Hill, KY

Vandalia Renaissance & Fantasy Faire

Organizer Vandalia Renaissance & Fantasy FaireUnclaimed

The Vandalia Renaissance & Fantasy Faire takes place October 9, 2026, at noon at the Carter County Shrine Club in Olive Hill. It features an artisan market, jousting and armored combat demonstrations, historic trade displays, and a medieval village with themed performers and food.

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Oct 9–10, 2026 Louisville, KY

Belknap Fall Festival

Organizer Belknap Neighborhood AssociationUnclaimed

The Belknap Fall Festival is a free, all-ages two-day outdoor festival held on October 9–10, 2026 in Louisville's Douglass Loop neighborhood. The event features live music on two stages, local food vendors, family activities (pumpkin painting, face painting, petting zoo), and a marketplace of local artists and vendors. It is produced by the Belknap Neighborhood Association.

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Oct 10, 2026 Shelbyville, KY

HorseSensing's Hometown Fall Festival & Craft Show

Organizer HorseSensingUnclaimed

HorseSensing is hosting our Hometown Fall Festival and Arts & Crafts Fair on October 10, 2026 from 10:00-4:00.Located on our beautiful horse farm in Shelbyville KY, we are excited to bring you a family fun event packed with arts & craft booths, food, fun and entertainment! Please join us as we welcome Fall in the Bluegrass!

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Deadline Oct 8, 2026

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Oct 10–11, 2026 Versailles, KY

26 Pumpkin Festival

Organizer Charismatic MediaUnclaimed

Pumpkin Festival at Wildside Winery Saturday, October 10 | 12–7 PM Sunday, October 11 | 12–5 PM Wildside Winery | 5500 Troy Pike, Versailles, KY Celebrate fall at Wildside with a full weekend of pumpkins, wine, music, and cozy vineyard vibes. The Pumpkin Festival is a seasonal favorite — the perfect place to wander, sip, shop, and soak in everything autumn has to offer. What You’ll Find Locally grown pumpkins for sale Beautiful mums Local artisans and vendors Pumpkin-spiced wine and seasonal drinks Live music all weekend (lineup announced closer to the event) A relaxed, family-friendly fall festival atmosphere Come for an hour. Stay all afternoon. Let fall happen around you. Admission is free. Wine, pumpkins, food, and vendor items available for purchase.

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Closed Sep 11, 2026

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Oct 10–11, 2026 Bardstown, KY

Bardstown Arts & Crafts Festival

Organizer Bardstown Main Street ProgramUnclaimed

Join us for the 45th Annual Bardstown Arts & Craft Festival in downtown Bardstown, KY. With over 250 vendors nationwide you will be sure to find something for the whole family to enjoy. 2026 marks the 45th anniversary of this rite of fall in one of Kentucky’s most beautiful and historic towns, Bardstown, KY. In addition to arts and crafts, patrons of the fair can enjoy food, drink and entertainment. Other attractions include a children’s area, demonstrations by local artists, and visitor information about our amazing small town. The annual Bardstown Arts & Craft Festival is a major fundraiser for the Bardstown Main Street Program. All proceeds are returned to our downtown community through family-friendly events, beautification projects, historic preservation efforts, and supporting small business. The Bardstown Main Street Program works hard as an organization to continue to make dow...

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Oct 10–11, 2026 Bardstown, KY

Bardstown Arts and Crafts Festival

Organizer VendorsMapUnclaimed

Join us for the 45th Annual Bardstown Arts & Craft Festival in downtown Bardstown, KY. With over 250 vendors nationwide you will be sure to find something for the whole family to enjoy. 2026 marks the 45th anniversary of this rite of fall in one of Kentucky’s most beautiful and historic towns, Bardstown, KY. In addition to arts and crafts, patrons of the fair can enjoy food, drink and entertainment. Other attractions include a children’s area, demonstrations by local artists, and visitor information about our amazing small town. The annual Bardstown Arts & Craft Festival is a major fundraiser for the Bardstown Main Street Program. All proceeds are returned to our downtown community through family-friendly events, beautification projects, historic preservation efforts, and supporting small business. The Bardstown Main Street Program works hard as an organization to continue to make dow...

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Oct 16, 2026 Lawrenceburg, KY

Anderson County Burgoo Festival

Organizer Anderson County Chamber of CommerceUnclaimed

The Anderson County Burgoo Festival returns to Main Street in Lawrenceburg, Kentucky, October 16 through 18, 2026. Organized in 1993, the festival has run annually since 1994, with live music and events centered at Century Bank Park and public parking available nearby.

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