If youre looking for an informal dinner spot without having to go change clothes you have plenty to choose from: Cheapside Bar & Grill, Furlongs (for authentic Cajun fare), Alfalfa, Stellas and the Caribbean-themed Atomic Cafe.
Day 3: Youve done the horses, now its time for the bourbon (needless to say, this works best if you dont have kids with you.)
Bourbon is Americas only native spirit (as declared by an Act of Congress,) and 95 percent of the worlds supply is distilled in Kentucky. There are six distilleries open to the public on the Kentucky Bourbon Trail, three of them within a half-hours drive of Lexington.
Woodford Reserve nestles on picturesque Glens Creek in Woodford County and is a National Historic Landmark. Its distilling tradition dates back to the early 1800s, and to this day, Woodford still uses the copper pot still method and ages the bourbon in stone warehouses. If you find yourself there around lunchtime, opt for a meal on the expansive terrace. Wild Turkey Distillery and Four Roses Distillery are both in Lawrenceburg. The former has a history dating back to 1855, and one of its main attractions is a 40-foot-high column still. The latter at first seems out of place in the Bluegrass with its Spanish-influenced architecture, but Four Roses bourbon is uniquely Kentucky.
No longer part of the trail but open to the public is Buffalo Trace Distillery in Frankfort, the oldest continuously operating distillery in the United States and the first to market single-barrel bourbon commercially. Learn all about the process on their informative tour, one of the best in the Bluegrass.
Upon your return to Lexington, you might want to continue the bourbon theme with a pre-dinner drink at the Bluegrass Tavern on Cheapside, which serves 178 different kinds of bourbon (bet you didnt know there were that many.) Follow that with dinner at The Julep Cup or the Merrick Inn (if the weather is nice, opt for the flower-filled patio.)
Day 4: How about a side of history to go with your entrée (horses) and beverage (bourbon)? Start at the spot where Lexington started McConnell Springs. Legend holds that it was here, in 1775, that a group of frontiersmen led by William McConnell got word of the Battle of Lexington in Massachusetts to start the Revolutionary War, and promptly named their campsite in its honor. Today, its a 26-acre nature preserve, with secluded trails and the Blue Hole natural spring.
If its antebellum history youre looking for, head out to Lexingtons southern outskirts for a visit to Waveland State Historic Site. This 10-room mansion was built in 1847 by an ancestor of Daniel Boone, and is one of the finest examples of Greek Revival architecture in Kentucky. Waveland and its surrounding 10 acres typify plantation life in pre-Civil War Kentucky.
Civil War buffs also have plenty to see in Lexington. The Gratz Park Historic Neighborhood has many beautiful Federal-style townhouses, one of which the Hunt-Morgan House, also known as Hopemont was the home of the Confederate Gen. John Hunt Morgan. The home now houses the Alexander T. Hunt Civil War Museum.
Statesman Henry Clay did his best to prevent the Civil War, and mementos of his distinguished life and career can be seen at his estate, Ashland. The 18-room Italianate-style mansion on Richmond Road is a National Historic Landmark, and its most popular features are the octagonal library with its domed rotunda and the formal English-style gardens.
While Clay did his best to keep the war from starting, another Kentuckian, Abraham Lincoln, ended it. Lincoln spent time in Lexington at the home of his wife, Mary Todd and her family. Beautifully restored, the Mary Todd Lincoln House on West Main Street is the first house museum in America to honor a first lady.