Where To Go Eat, Drink, & Enjoy Lexington, KY

Here’s where you can go eat, drink, and enjoy Lexington.  I’m sure I left out a place or two, so just email me to remind me, and if you know of any cool places I should check out next time I’m in town, just let me  know.  Thanks – Bernie


Other than University of Kentucky Basketball and Football, the main attraction in the Spring and fall is Keeneland:

***Keeneland Race Track is in Lexington, Kentucky and is quite an experience. Folks dress up a little more here and put on their hats at the meets here in April and early October races the 3 weeks before Churchill’s Spring and Fall meets

Downtown Food & Drink
Tony’s – 401 Main St – This upscale steakhouse is out of Cincinnati, which is like Lexington’s back yard for the Big Blue Nation (#BBN) of Wildcat fans in Northern Kentucky area. LIVE JAZZ some nights. This place has been great for downtown, so when ya want to treat yourself to something cool, stop by.

21c Museum Hotel – 167 W. Main – Great cocktails and fun restaurant with exotic flair here at this boutique hotel. 21c is a museum hotel which as has exhibits from contemporary artists of the 21st Century (21c…get it?). Probably the best cocktails in town, along with Bourbon on Rye and Bluegrass Tavern.

Bourbon on Rye – 115 Main St. – Another great cocktail bar, with a great bourbon selection. James owns the place and Chris runs the bar with his great staff. It’s my favorite place to drink whiskey and talk to folks about whiskey, and they have some pretty damn good food too. Stop on by, you won’t be disappointed.

**Bluegrass Tavern – 115 Cheapside – Local Legend Larry Redmon opened this place a dozen years ago or so, and this is a Certified Bonded Premises; C.B.P. KY-115. Hundreds and hundreds of whiskey bottles on the beautiful back bar, and a staff that’s well educated, and you can get a dang good drink or pour from a bartender in a white button down shirt and black tie. Larry sold the place a couple years ago, but it’s still the same great whiskey bar.

Jeff Ruby’s Steakhouse – 101 W. Vine Street – Newly opened in the Spring of 2019, this is a great steakhouse from  the famous restauranteur Jeff Ruby out of Cincinnati, OH, which is just a few dozen miles up I-75 from Lexington.

A MUST on MONDAY NIGHTS is Tee Dee’s Lounge – 266 E 2nd Street – not but a 10 minute walk from Portofino’s is one of the coolest experiences you’ll ever come across.  MONDAY NIGHTS is when I would suggest to everyone that’s visiting Lexington to go after dinner. The live music on Monday Nights doesn’t start until around 10pm.  Tee Dee is an amazing entertainer.  He’s a jazz/blues guitarist and vocalist.  His teenage son is as amazing as his father, and many of his family works at this club that’s been here for 25+ years.  Tee Dee and his family are the most down to Earth folks you’ll ever want to meet and they make everyone feel welcome.  There’s a nice lady at the front door that will take a $5 cover (CASH ONLY HERE, so bring $) and if you ask her how she’s doing, she will smile at you and say, “I’m blessed”.  They carry Old Fitzgerald Prime as their house whiskey. Treat yourself to some of the best live music you’ll ever experience!

Arcadium – 574 N Limestone – Beer, games, and spirits and old video arcade machines from the 1970’s and 1980’s. Great neighborhood tavern. Dog friendly

Belle’s – 156 Market St – This is a nightclub/bar venue that is more for the younger college crowd. Busy on the weekend. Nice rooftop bar.

Disillery District – at the James E. Pepper Distillery – 1228 Manchester St. with Goodfella’s Pizza/Wiseguys, The Break Room and others, great destination area to hop around to including the James E. Pepper Distillery

Goodfella’s Distillery – 1228 Manchester St; Distillery District in the old James Pepper Distillery. Probably the 2nd biggest whiskey collection behind Bluegrass Tavern here in town. Great pizza by the slice like a New York Slice (thus Goodfella’s) and good cocktails. This place is big, and you order slices up at the counter, so it’s good for large groups, or just a couple of ya.

The Break Room – 1178 Manchester Rd – This was the original Break Room for the James Pepper Distillery which this whole distillery area once was a part of back in the day. Today it’s a casual dive bar atmosphere, and good place to hang out in this hot distillery area.

Liquor Stores:
Justin’s House Of Bourbon – 601 W Main St
– Justin’s is a boutique liquor store, and they do conduct tastings. Kentucky passed the vintage spirits law, so that means Justin and his crew can hunt out and find old vintage dusties and other old whiskies distilled pre-prohibition, and from the 1930’s, 40’s, 50’s 60’s and 70’s. If you want to buy a piece of true bourbon history, stop in and look around.

Liquor Barn – Big box store, lots of store pick barrels from all distilleries.  3 locations, 1837 Plaudit Place, 921 Beaumont Centre Parkway (most of their distillers presentations happen at this location) and 3040 Richmond Rd.

Total Wine – two locations – 161 Lexington Green Circle, and 2321 Sir Barton Way

A Little Further Out

***Malone’s Steakhouse – 3347 Tates Creek – a great tradition after the races at Keeneland, or anytime, Malones is a great steak place and it’s a must for me when I visit.

OBC Kitchen – 3373 Tates Creek – Stylish place with Southern Fare, craft beer, and an extensive bourbon list. The bar isn’t big, so not the best for more than 2 or 3 people. But a great experience.

About bernie
-Whiskey Professor for Heaven Hill -2009 and 2012 Icons of Whiskey Award Winner - Whiskey Ambassador of the Year US and Global

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