Lexington, KY

A while back during a job interview in Sao Paulo, a senior executive asked me if I thought doing an MBA had been “worth it”… I didn’t hesitate then, and I don’t hesitate now and this trip to Lexington is another reminder of that.

Many of my best friends now belong to individuals in that MBA class and it is bittersweet to have them scattered around the world. While our constant communication has remedied so much of the physical distance (what they had for breakfast, what they did on the weekend, what music they’re listening to, the new piercings they got), I live for the moments where we find ourselves close again, learning what’s on their minds beyond the curated version of ourselves on social media, reconnecting and feeling that we are growing up together despite the distance.

One of the characters in this cast is a southern belle by way of Kentucky, North Carolina and California. She likes autumn, baking, horses, bourbon and took us to Lexington for three days to experience some of the things she loves most – including her adorable grandparents, who drove 2 hours to meet us for Sunday lunch and would not be resigned to let us pay for the bill.

To many more possibilities and to an inspirational group of girlfriends – looking forward to seeing what the rest of our lives will bring!

Stay:

21c Museum Hotel: A contemporary art museum and hotel with an adjoining restaurant. The room was simple but comfortable, the property a renovated official building complete with original floor tiles and mail chutes on the walls. The museum is worth a visit even if you are not a guest, it is open 24/7 and the art was thought-provoking. Fantastic concept located in downtown Lexington

Eat/Drink:

Sunrise Bakery: Unassuming bakery founded by Italian immigrants in the 1920s. I may have my NY ID card revoked but I thought their salt bagel was one of the best I’ve ever had – lighter than the NY standard. Great friendly service

Dudley’s on Short: Fancy dining room with white tablecloths in what looks like a renovated older house complete with a fireplace. Attentive, professional service. You must get the dessert with the marshmallow and brownie… no one wanted dessert at first until they saw this on our table

Holy Hill Inn: Slightly outside the city center, this historic home was converted to a restaurant after its previous reincarnation as an inn. Southern staples, delicious corn cakes, grits, honey glazed ham… and the artichoke fritters! Go here and feel transported back in time

Wallace Station: Simple sandwich and lunch shop with a strong local following. We had the chicken salad, artichoke fritters and burger. All very delicious and if you needed another reason to visit – Guy Fieri himself has also visited and approved this spot. What else do you need?

Bar Ona: If you are missing Brooklyn while in Lexington, head to this laid back bar. Lots of beards, beanies, wood paneled walls. Simple, good drinks

Do:

Keeneland Race Track: The winners of the races in April go compete in the Kentucky Derby. Extremely well organized, you will find Bet Experts who will show you the basics and the process of betting is highly addictive… I think they are on to something 😉 We had fun sitting and walking around the ground floor but the higher floors give you fantastic panoramic views of the track. I lost all my money but would do it again without a doubt

Woodford Distillery Tour: You know you’re in Kentucky for one of two main reasons – horses and bourbon. We enjoyed visiting this distillery where you see the fermentation process in action and then end the visit with an atmospheric tasting in their aging room among oak barrels

Winstar Farm: A recently established farm focusing on thoroughbred stallions. The tour was highly informative and the young tour guide extremely patient with both basic questions (what do horses eat?) and rapid-fire questions (what is the shortest time on record for a horse running the Kentucky Derby?). A special shoutout to Spot!

Old Friends: This is a retirement home for horses, many of them former racing champions. The story of the place is moving and the tour guide, Tom, was delightful in his dedication and love for the animals. Go here to support this great cause

Indigo Salon: After all that hard work visiting farms and drinking bourbon, it is only fair that you get yourself a massage. The space is relaxing and cozy inside an old factory/building carefully preserved and renovated to maintain a connection to its past (avoid throwing peanut shells on the floor!). Shawna is a very talented masseuse who in my post-massage bliss even convinced me to buy an overpriced massage cream… but I have no regrets!

Transport:

Flight: Only ~2 hours from NY, extremely convenient flight times

Car rental: There are Ubers and Lyfts, but driving is a pleasure with the rolling hills, quiet roads, white fences for days. Get a car and drive yourself

Thanks LW for a great trip