Kentucky Race Season Experience

A five-night stay at a boutique hotel featuring three rounds of golf, two bourbon experiences, and an exclusive Keeneland race day with Taylor Made Thoroughbred Farm. Private transportation is included for scheduled activities on Days Two through Five.

Keeneland's 2027 Spring Race Meet runs from Friday, April 2, through Friday, April 23.

BOOK BY DECEMBER 31, 2026

KENTUCKY RACE SEASON EXPERIENCE ITINERARY

PM: Arrive and Check In to Your Boutique Accommodations

DAY 1

Arrive in Kentucky and check into your boutique hotel for a five-night stay. Located in the heart of Central Kentucky, your hotel provides the perfect home base for exploring the region’s exceptional golf, world-class bourbon, and beautiful Thoroughbred horse country. Enjoy the remainder of the day at your leisure.

DAY 2 - Private driver experience for today’s scheduled activities.

AM:  Frankfort Country Club

Begin with a round of golf at Frankfort Country Club. This private club in Kentucky’s capital offers a scenic setting with tree-lined holes, elevation changes, and strategic bunkering.

FRANKFORT COUNTRY CLUB

PM:  Bluegrass Distillers Distillery and Cocktail Class Experience

Explore Kentucky bourbon at Bluegrass Distillers at Elkwood Farm, a craft distillery at historic Elkwood Farm in Midway. Discover its grain-to-glass approach to bourbon making, then enjoy a fun and interactive cocktail class in this distinctive Bluegrass setting.

BLUEGRASS DISTILLERS ELKWOOD FARM

DAY 3 - Private driver experience for today’s scheduled activities.

PM  Keeneland Owner’s Experience with TaylorMade Thoroughbred Horse Farm

KEENELAND RACE TRACK

Experience Keeneland as a racehorse owner with TaylorMade Thoroughbred Horse Farm. This elevated race day combines clubhouse hospitality with exclusive behind-the-scenes access, taking you beyond the grandstand and into the heart of Thoroughbred racing. Accompanied by an expert guide, follow the horses from the backside to the saddling paddock and feel the excitement of a live race from the Winner’s Circle. Enjoy lunch and an elegant clubhouse setting as you take in the pageantry and traditions of one of America’s most celebrated racecourses.

TAYLOR MADE FARM

DAY 4 - Private driver experience for today’s scheduled activities.

AM:  At Leisure

Enjoy an unhurried morning before the afternoon’s scheduled golf.

HISTORIC MIDWAY, KENTUCKY

PM:  Greenbrier Golf and Country Club

Play a round at Greenbrier Golf and Country Club, a private club in Lexington. The course and its longstanding golf traditions provide a relaxed setting for an afternoon in Kentucky’s Bluegrass region.

GREENBRIER GOLF & COUNTRY CLUB - HOLE #1 

DAY 5 - Private driver experience for today’s scheduled activities.

AM  The Woodford Club

Enjoy your final round at The Woodford Club in Versailles. The 18-hole, par-71 course winds through rolling Bluegrass countryside, offering a scenic finish to the golf portion of your stay.

THE WOODFORD CLUB - HOLE #13

PM:  Castle and Key Distillery Experience

Conclude the scheduled activities with a Castle and Key Distillery Experience. The restored Old Taylor Distillery pairs Kentucky’s bourbon heritage with distinctive castle architecture and landscaped grounds.

HISTORIC CASTLE & KEY DISTILLERY

DAY 6

Check out of the hotel and depart according to your own onward travel arrangements.

Transportation

Private transportation is included for the scheduled activities on Days Two through Five. Your driver follows the planned itinerary, providing seamless transportation between golf, bourbon, and racing experiences. Arrival and departure transportation is not included in this proposal.

Package Inclusions

Five nights at a boutique hotel; three rounds of golf at Frankfort Country Club, Greenbrier Golf and Country Club, and The Woodford Club; a Bluegrass Distillers Distillery and Cocktail Class Experience; a Keeneland day with TaylorMade Thoroughbred Horse Farm; a Castle and Key Distillery Experience; and private transportation for scheduled activities on Days Two through Five.

Double occupancy  |  $2,925 per person

Single occupancy  |  $3,675 per person

CLICK HERE TO GET STARTED RESERVING YOUR TRIP

The Kentucky Race Season Experience package is designed for groups of eight or fewer guests. Traveling with a larger group? We'd be happy to customize an experience to accommodate your needs. Please contact us at pam@kygolftrail.com to explore available options. Due to high seasonal demand and limited availability, substitutions to accommodations, golf courses, or experiences may occasionally be necessary. Any substitutions will be carefully selected to ensure a comparable level of quality and an exceptional Kentucky Golf Trail experience.

“Every member of our group enjoyed each experience you planned for us. It felt as though the experiences built on one another. All of the golf courses offered slightly different experiences. Thank you for making the birthday experience a memorable one. The pleasant bonus was finding that section of Lexington. We found ourselves there each day. 

Castle and Key was the cherry on top. A terrific tour of a large and historic distillery really was a nice capstone of our experience.”‍ ‍

‍ ‍- Philip B.