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Lexington, KY - All That, and a Bourbon Trail Too

Updated on December 4, 2014

Welcome to Lexington

Gateway to Bourbon

It's no secret that bourbon is really big these days. Even though some bourbon gets made inside Kentucky's borders, most Kentuckians will tell you all the best bourbon gets made here. With many distilleries spread around the state, Lexington is a great place to launch a bourbon discovery tour.

There also happens to be a couple of distilleries right in downtown Lexington. Town Branch and Barrel House both offer tours so visitors can get an up close look at how a mixture of grains and yeast gets turned into a very popular and distinctive version of whiskey.

Just west of Lexington, in the middle of horse farm country, Woodford Reserve is a beautiful example of what Kentucky's bourbon distilleries are all about. A bit further west, in the small town of Lawrenceburg, Wild Turkey and Four Roses produce some of the most sought after whiskey in the world. All three distilleries have recently upgraded their visitor centers and revamped tours to meet increased visitor demand.

Just south, in Danville, Wilderness Trail is part of the new Craft Bourbon Tour comprised of smaller boutique distilleries.



Lexington's craft beer scene has exploded in the last ten years or so. Just north of downtown, West Sixth Brewing and Blue Stallion not only make great beer, they've also regenerated their respective neighborhoods. Close by, Lexington Brewing Company shares property space with Town Branch distillery as both are under the same company umbrella.

Just south, in Danville, Beer Engine and Lore Brewing Company pioneer the craft beer movement for small town Kentucky.

West Sixth


The Lexington area now has a well established group of wineries to add to the bourbon and beer producers. Jean Farris and Equus Run are two local favorites.

Jean Farris, on Old Richmond Road, has a restaurant where you can match up a meal with wines like their Sauvignon Blanc, Viognier, Cabernet Franc and Cabernet Sauvignon, or might simply partake in a tasting of a range of the wine offerings.

Equus Run, just outside Midway, is a great place to tour the bucolic grounds and do a tasting of their wines like their very popular Riesling, Chardonnay, Vidal Blanc and Cabernet Sauvignon de Noir.

Jean Farris Winery



The revitalized downtown area is now home to a wide variety of dining and drinking options. In the Cheapside neighborhood alone visitors can choose from the tried and true Cheapside Bar and Grille as well as relative newcomers like Bluegrass Tavern, Parlay Social and Henry Clay's Public House.

Cheapside Bar and Grill

131 Cheapside St. Lexington, KY:
131 Cheapside Street, Lexington, KY 40507, USA

get directions


Shaker Village of Pleasant Hill

The very scenic Highway 68 takes you south to the beautifully preserved Shaker Village of Pleasant Hill. You can stay overnight for some quiet serenity or just have a pleasant lunch or dinner. You can also take a tour of the grounds that includes guides in period dress who explain how thing were done the Shaker way. There are also miles of bike and hiking paths across the expansive property.

Shaker Village

Shaker Village of Pleasant Hill

The Beaumont Inn

If you drive on west of Shaker Village of Pleasant Hill, on the very scenic Highway 68, you'll eventually come to one of Kentucky's older towns called Harrodsburg where the iconic Beaumont Inn is located.

Not only is the historic inn a great place to spend a quiet and tranquil night, it's also known for its delicious cuisine and its substantial bourbon offerings. If good bourbon appeals to you, there are two bars, the Owl's Nest and the Old Owl Tavern, where you can enjoy some hard to find whiskeys like Pappy Van Winkle, Old Weller Antique, E.H. Taylor and Willett Pot Still Reserve.

The Horse of Course

Even if your only mildly interested in horses and horse racing, there are two horse related places you should visit while in town. The Track Kitchen is a great place to have breakfast year round at Keeneland. If you happen to be in town in April or August, there's live racing to enjoy. There's also simulcast racing year round. In the fall of 2015, Keeneland will host the Breeder's Cup two day horse racing extravaganza. The eyes of the horse world will be focused on Keeneland and Lexington when the best thoroughbreds come to compete on the beautifully traditional racecourse.

The Kentucky Horse Park is a great place to learn about all kinds of horses from beast of burden draft horses to thoroughbreds. Several past champion race horses make KHP their home once their racing days are over. There's always something going on at the Kentucky Horse Park that people of all ages can enjoy.


Scenic Byways

There is a fascinating network of tree lined roads that originates around the Keeneland grounds and fans out westward toward Midway and Versailles.

At Keeneland, take the Back Gate Drive to Rice Road (1969), turn right on Rice Road to Van Meter Lane. Turn left on Van Meter Lane to Elkchester Road. Turn Right on Elkchester to Old Frankfort Pike (1681). Turn Left on Old Frankfort Pike to Highway 62 just south of Midway. Turn left on 62 to Highway 60, take a left on Highway 60 back toward Keeneland. Before Keeneland, take a left on Pisgah Pike. Stop at Pisgah Presbeterian Church to gander at the cemetery where former governor A.B. (Happy) Chandler is buried. Proceed on Pisgah Pike back to Old Frankfort Pike. At this point, you can go back to Keeneland or explore the many small roads that connect to Old Frankfort Pike. This drive runs by several beautiful horse farms and stately homes.

Dedmans Lane


The Lexington area isn't well known for its golf scene, but it should be. Golfers not only get to pick from several incredible public courses, they don't have to pay a lot to play. In Lexington, Kearney Hill, Golf Club of the Bluegrass, Connemara, Lakeside and University Club are all premium layouts.

Just south, in Richmond, The Bull and Gibson Bay are both well worth the short drive. In Mount Sterling, just east of Lexington, Old Silo is as beautiful as it is challenging. Just south, Peninsula is another fantastic track with some impressive vistas of the surrounding Kentucky countryside.

Old Silo



There are some great shopping venues all around Lexington. Fayette Mall has recently undergone an update that includes a new Cheesecake Factory along with plenty of other new stores. Hamburg Pavilion, east of town, has a bunch of upscale stores and restaurants. A brand new Summit complex is slated to open on Nicholasville Road in the near future.


There are several historic sites of note around town that reflect an influence on the state and nation. Ashland, home of vaunted politician Henry Clay, is a great way to get a feeling for Kentucky's past while enjoying the mansion's beautiful grounds. On Main Street, the Mary Todd Lincoln House is where the future first lady lived until she was 21. Waveland, just east of Lexington, gives visitors a look at what plantation life was like in antebellum Kentucky.



Tiny little Midway, just west of Lexington, is packed with unique shops and restaurants. Part of the fun of a trip to Midway is the scenic drive along Old Frankfort Pike where some of Kentucky's most prestigious horse farms line the route. Also on Old Frankfort Pike, just before reaching Midway, is Wallace Station where breakfast and lunch come with the restaurants legendary homemade breads.

Wallace Station


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