To experience the richest beauty of the always-beautiful bluegrass, plan your trip for either spring or fall. In April and May, not only are flowers blooming and trees exploding into green, but the year’s crop of foals are big enough to be gallivanting in the fields (many of them are born in January or February). And temperatures hover in the 60s and 70s—without the steaminess that comes in the summer months.
In autumn, the black walnuts and bur oaks turn gold, something that prompted Lexington journalist J. Soule Smith to say in 1898, “Sometimes, it seems to me that nothing can excel a woodland pasture in the fall.” No matter the time of year, remember that something has to keep the grass lush: Be prepared for rain (July is typically the soggiest time).
The best month to experience the equine lifeblood of Lex is April, when both the Rolex Kentucky Three-Day Event (cross-country, dressage, and show jumping) and the Keeneland meet (thoroughbred racing, including key Kentucky Derby preps) take place. But the whole region has a thriving art, music, and cultural scene during all four seasons. The Festival of the Bluegrass, in June, is Kentucky’s oldest bluegrass music festival. Fourth of July is the biggest holiday of the year—and the days-long party includes performances by the Lexington Philharmonic. September brings the Roots & Heritage Festival, founded to recognize the cultural contributions of African-Americans. Want to hit the Kentucky Bourbon Trail? There are tours (and free samples) all year, but some distilleries limit production in summer to fix up their facilities.
Winter in Kentucky can get quite chilly, with temps down in the 40s and 50s. If you can bear the cold, the holiday season is an experience in itself. A few inches of snow coat the horse pastures, and every tree and wreath shimmers with lights. The most snowfall comes in January and February, although it’s rarely more than a few inches.