Lexington, KY Horse Track

From horses to museums and shopping, Lexington has it all. The vibrant city is filled with Southern charm and hospitality and whether you live in the area, or just passing through, there are more than enough things to do in Lexington to keep you entertained!

Visit a Local Winery, Brewery, or Distiller

Looking for a lazy day activity or a new date night idea? Get a real taste of the south by visiting one of more than twenty-five wineries, breweries, or distilleries in the Lexington area! Lexington might be known as the birthplace of bourbon, but Brewgrass Trail is expanding our horizons by featuring local craft brewers.

Fun Facts:

  • The first commercial grape growing operation in the United States was in the Bluegrass Region of Kentucky.
  • Each of the Brewgrass Trail breweries offer brewery passports – have it stamped by each brewery you visit and Visit Lex will send you a one-of-a-kind t-shirt!
  • More than half of the wine produced in Kentucky comes from fruit and berries (other than grapes!).
  • Bluegrass Tavern in Cheapside Pavilion is known for being one of the best bourbon bars in the South, with a bourbon selection over 450.
  • 95% of the world’s bourbon is aged in Kentucky and there are nine distilleries within 35 minutes of Lexington.

Visit a Historic Home

There’s a lot of history in Lexington, and the best way to start taking it all in is to visit the historic homes of the some the area’s most famous citizens: Mary Todd Lincoln, Henry Clay, John Hunt Morgan, and Joseph Bryan.  

Each historic home is open for tours, showcase several different architectural styles, and include family pieces, period antiques, and personal possessions.

Spend the Day at Keeneland Race Course

As the Horse Capital of the World, there are several horse-related activities in Lexington between the Kentucky Horse Park, Horse Farm Tours, and our favorite – the Keeneland Race Course.

With a tranquil setting and old stone buildings, the historic landmark is one you simply cannot miss. If you’re feeling lucky, attend one of the live Thoroughbred races that take place between April and October. If horse races aren’t your cup of tea, the race course also offers tours year-round, in addition to several spaces that can be utilized for events of all kinds.

Enjoy Downtown Lexington

A quick ten-minute drive from the 1809 at Winchester property, the casual, cosmopolitan atmosphere of downtown Lexington, the area bolsters big-city amenities and small-town friendliness. With a variety of attractions, restaurants, shopping, and entertainment, visiting downtown Lexington is a great activity day or night.

Our Favorite Attractions, Restaurants, and Shops:

  • Explorium of Lexington – The 14,000-square foot children’s museum is located within a complex of 16 restored 19th century commercial buildings and features a variety of hands-on activities in The Square.
  • The Square and The Shops at Lexington Center – Two of the most popular shopping areas in Lexington, The Shops at Lexington Center features exclusively Lexington shops such as Old Kentucky Chocolates and The Square features newer stores, including Urban Outfitters.
  • Parlay Social – A speakeasy-style lounge on the corner of Market and Short, Parlay Social offers cocktails, pub grub, and even has live music.

Experience Shaker Village of Pleasant Hill

A landmark destination might not be in Lexington, but it’s just a 45-minute drive! With over 3,000 acres and 34 restored 19th-century buildings, Shaker Village offers hands-on classes, musical entertainment, and special events to ignite your curiosity. Whether you’re visiting for the day with your family or spending the night with a loved one, you won’t be disappointed in your trip!