Welcome to October, locals! Can you believe we’re in the month of Halloween already? October is such an awesome time of the year, especially in Central Kentucky where fall rolls in slowly and stays awhile. Get out there and enjoy! This week I took a different approach to events. You’ll have to let me know what you think (you can reply to this email).
—Tommy
October 2025 Events Around Lexington
Looking for something fun to do this month? We’ve rounded up the best family-friendly events in Lexington and nearby, plus a few can’t-miss festivals in Louisville and Cincinnati. Mark your calendars, grab the kids (and maybe a sweater), and let’s make October memorable!
🌟 Louisville Jack O’Lantern Spectacular
📅 Oct 2–Nov 2 | ⏰ Dusk–11 PM | 📍 Iroquois Park, Louisville
Thousands of glowing pumpkins create one of the region’s most jaw-dropping displays.
👉 More Info
🧟 Halloween Festival & Thriller Parade
📅 Oct 26 | ⏰ 4:45–9 PM | 📍 Downtown Lexington
Vendors, costumes, and the iconic Thriller zombie dance in the streets!
👉 More Info
🐴 Keeneland Kids Club Family Day
📅 Oct 12 | ⏰ 11 AM–3 PM | 📍 Keeneland
Free general admission, kids’ activities, and racetrack fun — a fall tradition.
👉 More Info
🎃 Jack-o-Lantern Trail (McConnell Springs)
📅 Oct 22–25 | ⏰ 6:30–10 PM | 📍 Lexington
A magical half-mile trail glowing with carved pumpkins, campfires, s’mores, and even live owls.
👉 More Info
Fat Bear Week’s Undisputed Champ
Fat Bear Week ran Sept. 23–30 and the internet crowned a clear winner. It’s an easy, fun way to get kids curious about wildlife, migration, and how animals prepare for winter.
13 Kentucky Schools Honored at 2025 Continuous Improvement Summit
A Lexington school was among 13 Kentucky schools and districts honored last week for innovative “best practices” in education. These awards spotlight the creativity shaping classrooms across the Commonwealth.
Kentucky Basketball Gives Back at the Hope Center
The Wildcats stepped off the court this week to serve meals at Lexington’s Hope Center, bringing optimism, food, and smiles. It’s a reminder that Kentucky basketball isn’t just about winning games—it’s about showing up for the community.
Italian Comfort Food in Hamburg
I have fallen in love with Smashing Tomato, right here in Hamburg. From fresh, hand-tossed pizzas to scratch-made pastas, it’s the perfect spot for a date night.
Red River Gorge & Natural Bridge: Day Trips Worth the Drive
Just an hour from Lexington, these Kentucky treasures are perfect for a family adventure in the crisp October air.
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Thanks for reading — we’ll see you next week.