Becca and Jess's first date!
Upscale, glamorous, and ideal for tuxes + gowns. Known for prime steaks, sushi, cocktails
A longtime Lexington favorite offering refined American cuisine in a classic downtown setting. The rooftop patio is especially lovely in the evening.
Elevated Southern cuisine with an incredible bourbon list. Rehearsal-dinner-worthy.
You’re officially in bourbon country. Great nearby stops: • Woodford Reserve (20 min) • Castle & Key Distillery (10 min from the Castle) • Bluegrass Distillers (Lexington) • Barrel House Distilling (walking distance from Lost Palm)
A date night both Jess and Becca love! Great wine, amazing wine flights, great snacks and vibes.
October is prime season—cool weather, beautiful foliage, and active training. • Spend a morning at Mill Ridge, Claiborne, or Spendthrift Farm. • Tours fill quickly; book ahead!
Gorgeous fall colors, quiet walking paths, and perfect for guests wanting a slower-paced morning.
October is fall racing season — electric atmosphere, cocktails, and hats. Even if there’s no meet, the grounds are beautiful for a morning stroll. It is also Keeneland season! A perfect time to catch a few races before the big day!