The Good Life
with a Southern Drawl

The Perfect Day In Lexington

By Amy Bailey — October 01, 2018

Rolling green hills dressed in wildflowers, thoroughbreds grazing behind white fences that sweep along the highway, this is Lexington, Kentucky. Behind the obvious reasons to visit – horses and bourbon – there is a town full of charm, creativity, and fun for the whole family that is staking its claim in the modern South.

Where To Stay

Gratz Park Inn – The Gratz Park Inn sits on land first settled in 1781 and is conveniently located in historical Lexington with downtown in easy walking distance. The hotel exudes Southern hospitality with nicely furnished rooms, a beautiful library,and even gardens to sit and relax in.

21c Museum Hotel – If you are looking for a more contemporary feel. This 88 room boutique hotel was voted Top 5 Best New Hotels in 2016 by USA Today. The most unique part of 21c is the 7,000 square feet of museum space that is housed under the same roof as the hotel from the sidewalk to the lobby featuring local and global artists. The hotel is also home to Lockbox, one of Lexington’s premier dining experiences led by chef Jonathon Searle, featuring many local and Kentucky ingredients. Enjoy plush, modern rooms.

Where To Eat

Third Street And Stuff – One of the coolest coffee shops I’ve ever been in. Enjoy reading the walls outside and inside while browsing the art. Third Street serves up Fair Trade, Certified Organic, locally roasted coffee, breakfast, and sandwiches. They also have a slew of unique, creative gifts to shop too.

Shakespeare and Company – A beautifully decorated, funky restaurant serving delicious food. This restaurant is always bustling with energy and good vibes. Enjoy a diverse, ever-changing menu and great cocktails 7am until 12am.

Lockbox – Led by executive chef Jonathan Searle, the menus at Lockbox showcase a deep network of local providers and the bounty of ingredients fed by Kentucky’s limestone-rich soil.

Crank and Boom – With a commitment to all natural, local ingredients, Crank and Boom is a MUST visit. Enjoy a flight of ice cream and any of their signature flavors: Bourbon & Honey, Kentucky Blackberry & Buttermilk, Dark Chocolate Truffle, Coffee Stout, Vanilla Bean, Blueberry Lime Cheesecake, SuperFudge, Fresh Strawberry, and Salted Caramel.

What To Do

If you are looking for a reason or special time of year to visit Lexington, here is an extensive list of events throughout the year.

Historic Downtown Walking Tours – Learn about the history of downtown Lexington as reflected in its historic homes, churches and commercial buildings. See Henry Clay’s law office, Christ Church Cathedral, Transylvania University, the pre-civil war homes of Gratz Park, and more. Regular tours offered on Mondays, Wednesday and Fridays, as well as custom group and private tours by appointment.


PRHBTN – PRHBTN is an annual celebration of art forms that have been criminalized, marginalized, and under-appreciated in the mainstream, featuring public murals alongside an exhibition of street art works in a space that complements the raw, powerful nature of the message and artistry of each piece. You will see murals as you walk along downtown Kentucky. The gathering of artists from  around the world usually occurs in October.

Shaker Village of Pleasant Hill – Something the whole family will enjoy is a visit to Shaker Village of Pleasant Hill just 30 miles South of Lexington. You can stay, dine, or just enjoy the day with incredible activities and events throughout the year. Regularly occurring events include riverboat rides, paddleboarding, cycling, music on the lawn, horse drawn carriage rides, and gardening classes. Special events include Hard Cider Fest, Harvest Fest, Halloween Boo! Cruise, Spirit Strolls, Family Quail Dinner, and Blessing of the Hounds.

Old Friends Thoroughbred Retirement Farm – In a little more than a decade Old Friends, the Thoroughbred Retirement Facility in Georgetown, KY, has put a new face on the concept of equine aftercare. Founded in 2003 by former Boston Globe film critic Michael Blowen, the organization has grown from a leased paddock and one horse to a 136-acre farm, a herd of over 175 rescued and retired horses. March 15 – November 4, tours are daily at 10 am, 1 pm & 3 pm. Winter hours are November 5- March 14 – one tour daily at 11:00 only. Reservations are required and can be made online by clicking here.

Kentucky Bourbon Festival – What better way to celebrate Bourbon. Enjoy a week of events, tastings, music, and more in Bardstown.

National Horse Show – America’s oldest indoor horse show. Dates: Venue: Kentucky Horse Park. Recurrence: Recurring daily.

Southern Lights – The Southern Lights includes a self-guided four mile journey through a dreamland of fabulous light displays including never-before-seen displays and traditional favorites. Following the driving tour, families are encouraged to park and visit the holiday craft merchants, the KHP Gift Shop, seasonal entertainment and activities for children, petting zoo, pony and camel rides and so much more!

Breyerfest – Have a little girl who loves Breyer ponies? This is the ultimate Breyer event with special models, horse shows, meet and greets, and photo and autograph opportunities. Venue: Kentucky Horse Park.