Fall Fun in Lexington

Fall is the best time of year to visit the Bluegrass region, not only is it full of gorgeous views, but there’s no shortage of things to do in and around Lexington. Whether you’re exploring the bluegrass countryside, or admiring downtown’s laid back yet quirky charm, there’s simply nothing like autumn in Lexington.

Natural Bridge Arch with Sun in the Background

Gray's Arch at Red River Gorge

At Red River Gorge, you’ll find up-close and personal views of changing leaves, gorgeous natural waterfalls, and stunning natural hiking trails. Beyond the views, there’s also ziplining, rock climbing, and underground kayaking. Yes you heard that correctly, the guided kayak tour through the Gorge Grotto is an hour-long adventure underneath the Earth’s surface. Adventure to the Kentucky Palisades, an ecosystem that is over 450 million years old. The Palisades consist  of limestone cliffs, deep gorges, springs, hiking trails, and a cave system. Fully immerse yourself in the experience by paddling along the Palisades on the Kentucky River via kayak. You’ll get a unique view of the blue ash, sugar maple, and poplar trees as they change color, and you may even get a look at wildlife in their natural habitat. And for those who prefer a faster-paced excursion, there’s bike tours on Lexington’s Legacy Trail. The Legacy Trail is not only a great way to get some exercise, but it provides a unique view of the foliage surrounding Lexington. Another unique way to catch some fall views is canoeing along Elkhorn Creek. It’s also the perfect place to do some fishing for smallmouth bass, channel catfish, and rock bass, but make sure you have a fishing license. Want to kayak the Elkhorn? Check out Canoe Kentucky.


Exterior of Eckert's Boyd Orchard

Eckert's Boyd Orchard

It wouldn’t be fall without a trip to an orchard. Eckert’s Boyd Orchard is one of the finest in the Bluegrass, with its gorgeous pumpkin patch and apple picking orchard. Although it doesn’t stop there, Eckert’s also grows a variety of other fruits like peaches, blackberries, and strawberries. This is the perfect place for the whole family, with activities like haunted hayrides, the corn maze, gem mining, and delicious foods like their famous apple cider donuts.


Country Boy Brewery Background

Country Boy Brewing

Speaking of fall flavors, Country Boy Brewing has released their new Keeneland Fall Ale. This 5.5% Pale Ale is meant to complement the crisp fall weather that fans associate with Keeneland’s Fall Race Meet. As one of the most beautiful Thoroughbred race tracks in the world, don’t miss the 2021 Keeneland Fall Meet October 8th-30th.


People on a tour at the Woodford Reserve Distillery

Woodford Reserve Distillery

Craft beer may be a great autumn refreshment, but Lexington is known for its bourbon, which pairs even better with the fall season. There’s a healthy helping of distilleries around Lexington, including Woodford Reserve and Buffalo Trace Distillery. If you prefer your bourbon with a meal however, there’s no shortage of dining options in Lexington. One such place is Bourbon on Rye. A modern art-deco inspired restaurant with a signature cocktail menu including one of the best Old Fashioned’s in town, and trust us, there’s a lot of competition.


Aerial of The Kentucky Castle

The Kentucky Castle

One of the best parts about fall is Halloween, and there’s no shortage of spooky spectacles in Lexington. For starters, there’s the Lexington Cemetery, which doubles as a nationally recognized arboretum. It houses over 200 different types of trees, an array of picturesque ponds, and fascinating monuments—making for a sight you truly will not forget. The Bi-Water Farm AutumnFest is another place to catch a fright. It features hayrides, a corn maze, pumpkin vine zip lines, it’s signature Spooky Farm House, and even paintball shooting. Finally, top it off with a visit to The Kentucky Castle. This gorgeous four-steepled castle has an impressive double iron-door entrance, and an even more impressive interior. What makes it spooky though? Local legend has it that the castle is haunted, although that’s up for debate.

Top 13 Things to Do

Horse farm tour

Horse Farm Tours

lexington - horses - sample itinerary

Bourbon Distilleries

Group of people touring Woodford Reserve Distillery

Historic Homes

Ashland - Henry Clay Estate

Free Things To Do

A woman photographs her friend posing for a photo in front of a series of huge, vibrant murals.

Brewgrass Trail

Two women cheers their beers and smile inside the tasting room of Mirror Twin Brewing.