Autumn in Kentucky: What to do?

Ashford Acres Inn • August 30, 2019

The early morning air is beginning to feel a little more crisp, the kids are off to school, coffee shops are preparing their pumpkin flavors and soon the leaves above our heads will be changing colors and carpeting the ground beneath our feet. 

Fall is on it’s way to Kentucky!

Dust off your knee high boots, freshen up the scarves you stored away in late spring and get your calendar out to make your fall-in-Kentucky plans!

Check out some of our favorite things to do in Kentucky during this cool and colorful season.

  • Let’s start with a Kentucky classic – Horses. 

Have you visited Whispering Woods Riding Stables yet? If not, gather some friends of all ages and plan a day to horseback ride through true Kentucky woods. It’s such a unique and fun way to enjoy nature and spend a little time with the magnificent creatures our state is known for. I’ve been on many trail rides in my life – on mountainsides, on the beach, in pastures…but this was definitely my favorite equine adventure. 

Visit http://whisperingwoodstrails.com for information on how to plan your fun, fall horseback riding experience!

Another fun horse themed escapade during fall is visiting Old Friends Thoroughbred Retirement Facility where retired race horses now reside, grazing on Kentucky bluegrass and freely galloping through beautiful green pastures. Fall is the best time to visit Old Friends because the heat and humidity of summer has given way to cooler temperatures and wilted leaves, making your walk between the fences much more comfortable. Be sure to visit Little Silver Charm, who we think is just as entertaining and interesting as all of his taller companions on the farm.

Visit http://www.oldfriendsequine.org  for information on attending a tour.

  • Take a stroll in downtown Cynthiana and get a jump start on your holiday shopping!

Sometimes you need to get away from the fast-paced worlds of work, school, and kid sports schedules. Take a break by strolling along downtown streets filled with unique boutiques, florists, an antique store, a super charming hardware store, a coffee shop, a town museum, restaurants and a brewery. Grab a beer, a bite to eat, take pictures in front of towering murals and if you time it right maybe also catch a movie in one of the oldest movie theaters still showing first-run movies, Roh’s Opera House. (Photo by Shonda Judy)

  • Can you close the fall season without a good trip, or two, or three to the pumpkin patch? We don’t think so!

Our family favorite pumpkin patch is Bi-Water Farm in Georgetown. We’ve made so many family memories on the hayrides, searching for the perfect pumpkins, watching the bunnies hop around their little town and watching the little ones climb around on the playground. Bi-Water provides fun for the entire family and we suggest picking up a jar of homemade apple butter before you head back home with your wagon full of pumpkins!

Visit https://biwaterfarm.com  to view operating hours.

  • Drinking bourbon is, and should always be, an any-day-of-the-year experience in Kentucky. However, we personally find the fall climate with the turning leaves to be a favorite time to visit a bourbon distillery and taste-test Kentucky’s spirit.

It’s difficult to pin down a single bourbon distillery as being the best. There’s a reason the Bourbon Trail is known throughout the world! Visitors never forget the beauty of the countryside witnessed not only at individual distilleries, but also on scenic drives to the distilleries. One of our favorites to visit is the Woodford Reserve Distillery in Versailles. This world renown bourbon has built it’s own reputation as a near-perfect whiskey, but we believe whole-heartedly (and try hard to live up to this belief at Ashford Acres Inn with our own guests) that the quality of your experience makes everything taste better. Tasting your Woodford Reserve bourbon AT the stunning piece of Kentucky property where it’s made might just make it the best bourbon you’ve ever savored.

  • Regardless of the state you’re in, fall festivals are a staple for the season. We might be slightly biased, but we believe fall festivals in Kentucky are the BEST.

To us nothing says fall better than parking in a grass field, shopping for crafts under big, white tents and searching for that once-a-year delicious treat of freshly made doughnuts sold out of a trailer, (which happens to sit very near the blacksmith’s cabin toward the back of the festival. We’ve done this once or twice before). The particular festival we’re referring to is Kentucky’s famous Wool Festival in Falmouth. This juried craft festival is a favorite for Kentuckians and cannot be missed! With endless booths of crafts, live music, a wool and sheep tent that gives the festival its name, shearing and herding demonstrations, and more yummy food trucks than we have room to list, this is the epitome of fall festivals!

Visit  http://www.kywoolfest.org  for more information about this year’s Wool Festival.

  • Go hiking and look at those autumn colors! Fall is the perfect time to explore Kentucky’s landscape. 

There are countless hiking trails throughout the state showcasing diverse and exquisite scenery. Various ability levels of trails throughout the state will lead you to natural bridges, flowing streams and stunning waterfalls. Very close to Ashford Acres Inn is Quiet Trails State Nature Preserve, which provides an easy 1.7 mile loop, making it perfect for family hikes, with views of the Licking River. Fall is the perfect time of year to renew your love and fascination with Kentucky’s countryside! We suggest packing a picnic and enjoying an entire afternoon in nature!

Tell us some of your favorite things to do during fall in Kentucky!

Annastasia’s favorite season is fall and so of course, she has a Kentucky fall bucket list! 

  • Visit the pumpkin patch
  • Make chili
  • Have hot cocoa on the front porch
  • Have a picnic in the cool fall air
  • Go hiking
  • Watch Hocus Pocus with friends
  • Roast pumpkin seeds
  • Go to fall festivals
  • Bake a pie
  • Take a family fall photo
  • Decorate the house for fall
  • Go star gazing
  • Take a scenic drive
  • Have a bonfire
By Ashford Acres Inn • September 2, 2026
There is something about fall in Kentucky that feels almost made for a movie: winding country roads, historic small towns, rolling Bluegrass farmland, changing leaves, front porches, warm drinks and evenings spent around a fire. At Ashford Acres Inn in Cynthiana, Kentucky , you don’t just visit that version of fall - you get to stay in the middle of it. Located just 45 minutes from Lexington, about an hour from Cincinnati, 1.5 hours from Louisville, 20 minutes from Georgetown and 15 minutes from Paris , Ashford Acres is an easy Kentucky fall getaway that somehow feels much farther away from everyday life. A Kentucky Town Made for Fall Cynthiana has earned recognition as a top fall destination in Kentucky, and once October arrives, it isn’t difficult to understand why. Historic downtown Cynthiana delivers the kind of small-town autumn atmosphere that feels straight out of Gilmore Girls or a Hallmark movie. Spend an afternoon wandering downtown, popping into locally loved stops like Fibonacci Antiques, Uniques Antiques, The Next Chapter Bookstore, Maime’s Fine Wines & Gifts, or Pike Street Wine House - then leave town behind and drive just a few minutes into the countryside to Ashford Acres. That is what makes a fall stay here so special: you don’t have to choose between a charming Kentucky small-town getaway and a peaceful countryside retreat. You get both. Add a Little Ghost Story to Your Fall Weekend For nearly two decades, the Cynthiana Ghost Walk has been one of the community’s signature October traditions. The lantern-led walk takes guests through historic downtown before heading inside the historic Rohs Opera House, built in 1871 and described by the Ghost Walk itself as the third-most-haunted building in Kentucky . It’s not a haunted house filled with actors and jump scares. It’s local history, storytelling, reported paranormal experiences and evidence collected during previous investigations—all unfolding in the actual places where the stories originated. For guests who want to build an entire stay around the spooky side of Cynthiana, Ashford Acres now offers The Ghostly Getaway package for two. It includes Cynthiana Ghost Walk admission, The Ashford Files filled with stories, history and mysteries, a spooky arrival sip, lanterns for an evening walk, a fall treat, s’mores and a fire pit, a Halloween movie snack basket and a seasonal fall candle to take home. Or Spend 64 Acres in Fall If your ideal autumn weekend is less spooky and more cozy, our 64 Acres of Fall package was created for exactly that. The package includes seasonal cocktails or mocktails, charcuterie for two, s’mores beside your personal fire pit, hot chocolate or cider, a seasonal candle and a one-hour farm tour of Ashford Acres . And that farm tour isn’t simply a walk around the property. Ashford’s main house was built in 1858 , and pieces of the property’s history are still visible throughout the grounds—from the old carriage step built into the rock wall to the mill wheel and other remnants of generations who lived and worked on this Kentucky land. You’ll hear about the history of the home while also getting a look at what Ashford is today: a working 64-acre property with gardens, animals, hospitality, events and a team caring for it every day. Fall at Ashford Doesn’t Need an Itinerary Some of our favorite fall experiences aren’t scheduled at all. Take a walk along the grass trails as the leaves begin changing across the Kentucky countryside. Visit the animals. Find an adirondack chair with a beautiful view. Wander through the garden as it completes another growing season and begins its transition into rest and rehabilitation for the year ahead. Go fishing at the pond. Sit on the front porch. Bring a book outside. Watch the sun disappear behind the rolling hills. Later, order a seasonal cocktail made with house-made purées, local bourbons and thoughtfully selected spirits. End your evening with a fireside nightcap, hot cider or s’mores. The point isn’t to squeeze as much as possible into a weekend. Sometimes the best part of a Kentucky fall getaway is finally having somewhere beautiful enough to do absolutely nothing. Build Your Stay Around a Fall Event Fall is also one of our busiest seasons for experiences at Ashford Acres. Guests can visit our Events page before booking and curate an overnight stay around one of our seasonal events. Our 2026 fall calendar currently includes September reservation dining evenings, Spookeasy at Ashford on October 30 , our Halloween Festival and Halloween Tea on October 31 , and our annual Fall to Table Dinner on November 21 , among other experiences. Come for an event. Stay for the night. Wake up in the Kentucky countryside. Or make Ashford the home base for an entire weekend of exploring Cynthiana. The Kentucky Fall Weekend You’ve Seen in the Movies - Only Real Maybe that’s the easiest way to explain fall at Ashford Acres. You know the town in the movie where everyone wanders into local shops, knows the historic buildings, tells old ghost stories and celebrates the changing seasons? That’s Cynthiana. And you know the beautiful country inn just outside town where the characters retreat afterward…the historic house surrounded by fields, fireplaces, porches, animals, gardens, good food and enough quiet to hear the leaves moving? That’s Ashford. Except this time, you actually get to stay there. Whether you’re searching for a romantic fall getaway in Kentucky , a bed and breakfast near Lexington, KY , a quiet weekend away from Cincinnati or Louisville, or simply one of the best places to experience fall in Central Kentucky , Ashford Acres Inn gives you 64 acres to slow down and experience the season. Fall is waiting at Ashford Acres Inn. Explore our current lodging packages, choose your suite and start planning your fall stay at Ashford Acres Inn , or browse our upcoming events at Ashford Acres to build your getaway around something special. -Ashford Acres Welcoming Team
By Ashford Acres Inn • June 16, 2026
"Cynthiana hospitality is warm, welcoming, and feels like family."
By Ashford Acres Inn • May 2, 2026
"It may be no surprise to some, but the parts of wedding planning I have found sweetest, are those you can only do as the bride herself."