Lucky you. You just found LEXtoday’s Plan Ahead, a list of some of the biggest events to plan for that are taking place throughout the Horse Capital of the World each month.
Take out your calendar, grab your day planner, or text all your friends — these are the top events we recommend heading to this month. Psst: Don’t forget to bookmark this page and come back; we update our guide monthly.
(Don’t see anything you like? Check out our full events calendar.)
Music + comedy
Music at The Mansion | Friday, Sept. 5 | 6-10 p.m. | Marriott Lexington Griffin Gate Golf Resort & Spa | Price of purchase | Grab your lawn chair, relax with local vendors, and enjoy the last days of summer with this month’s band, One More Round.
Jimmy Buffett Party | Saturday, Sept. 6 | 9 p.m. | Neon Moon | Price of purchase | Grab a free lei, sip tropical cocktails, wear Hawaiian attire, and enjoy Jimmy Buffett tunes — spend the night on island time.
I - We - Y Inclusive Music Festival | Saturday, Sept. 13 | 12-9 p.m. | Manchester Music Hall | Free | Enjoy a full day of live music, interactive activities, local food, and community resources in a fully accessible, inclusive environment for all ages and abilities.
Napoleon Dynamite Live! | 8 p.m. | Lexington Opera House | $52+ | Watch a full screening of “Napoleon Dynamite” followed by a lively, moderated discussion with fan-favorite cast members Jon Heder, Efren Ramirez, and Jon Gries.
Seasonal events
Kentucky Horse Park Flea Market | Saturday, Sept. 20 | 9:30 a.m.-4 p.m. | Kentucky Horse Park | $10 | Come treasure hunting at the scenic Kentucky Horse Park — browse a variety of unique finds, antiques, crafts, collectibles, and more.
Parktoberfest | Saturday, Sept. 6 | 3-9 p.m. | Ashland - The Henry Clay Estate | Price of purchase | Toast the season with traditional steins, authentic German beers, and live tunes in a vibrant community gathering.
For the fam
Doggie Paddle 2025 | Saturday, Sept. 6 | 9 a.m.-12 p.m. | Southland Aquatic Center | $10+ | Bring your furry friend for a day of splashing, shopping local vendors, exclusive LHS merchandise, and exciting raffles.
Swiftie Sing-Along and Dance Party | Saturday, Sept. 6 | 6-9 p.m. | MoonDance Amphitheater | Price of purchase | Sing and dance your heart out to the full Eras Tour setlist, complete with themed outfits, food trucks, and Swiftie community fun.
2025 Wiener Dog Races & Doggie Dash | Sunday, September 21 | 10 a.m.-4 p.m. | Red Mile Gaming & Racing 1200 Red Mile Road | $24.57 | Get ready for the cutest and most exciting race of the year, where these adorable pups will sprint their way to victory.
Classes
Pasta 101 Class | Friday, Sept. 5, Friday, Sept. 19 | 7-10 p.m. | Pasta Garage Italian Cafe | $106 | Sharpen your cooking skills as you and 20 others learn how to make fresh pasta from scratch, while enjoying appetizers, wine, dinner, and dessert.
Teen Cooking Class | Tuesday, Sept. 16 | 4-6 p.m. | Dunbar Center | Free | Calling all young chefs to show off their cooking skills at this interactive class where teens will learn how to make a homemade crust pepperoni pizza.
Festivals
36th Annual Lexington Roots & Heritage Festival | Friday, Sept. 5-Sunday, Sept. 7 | Times vary | Elm Tree Lane | Price of purchase | Honor African-American culture and local communities with food, music, performances, a parade, educational programs, and local vendors.
Apple Festival | Saturday, Sept. 6-Sunday, Sept. 7 | Times vary | Evan’s Orchard, Georgetown | $12+ | Celebrate apple season with fun for all ages — hayrides, corn maze, paintball, slides, apple cannons, music, and more.
Festival Latino de Lexington | Friday, Sept. 19-Saturday, Sept. 20 | 5-11 p.m. | Downtown Lexington | Price of purchase | Celebrate Latin American art and culture with live music, dance, visual arts and tasty food vendors.
Get Social
Poetry at the Table | Wednesday, Sept. 3 | 5:30 p.m. | Kenwick Table | Free | Join us on the first Wednesday of the month for an evening of poetry, including featured performers, an open mic, and the most supportive audience in Lexington.
Book Swap | Saturday, Sept. 6 | 12-4 p.m. | Blue Stallion Brewing | Free | Swap up to five gently used books — including children’s and adult titles — for new reads from the community in a fun, free, low-cost event that also supports the taproom’s small library.
Wine & Fries | Friday, Sept. 12 | 5:30 p.m. | The Campbell House | $50+ | Indulge in McDonald’s fries and hand-selected wines at Wine & Fries, supporting Ronald McDonald House Charities of the Bluegrass with tastings, games, prizes, and fun experiences.
Have an event of your own you want to share with us? Follow these easy steps to add your events to our calendar:
- Go to our Events page.
- Click “Add Event” in the top right-hand corner.
- Make sure to include a link and fill out important information like the date, time, location, and price of your event.
- Click “Submit,” and you’ve just added an event to our website calendar.