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Day Trip Itinerary: Pin Oak Stud and Woodford Reserve

Central Kentucky is a region known for producing the world’s best racehorses and Bourbon. Some of the world’s top horse farms and distilleries sit among the rolling hills of the Bluegrass. Follow this itinerary for a full day exploring Kentucky’s Horse Country, including an interactive horse farm tour, locally-sourced meal and distillery tour.

This itinerary is based off of tour offerings in Summer and Fall of 2026.

TOUR

10:30 a.m. – 12 p.m.

See how racehorses are trained and cared for on a tour of the Pin Oak Training Center. Pin Oak’s private training center includes a dirt training track, turf gallops, multiple barns with wide shedrows, ample paddock space for turnout and more. Learn how racehorses are kept in peak condition, and meet some of Pin Oak’s racehorses.

The Pin Oak Stud Training Center Experience is offered on most weekdays at 10:30 a.m., which can be booked by clicking here.

Pin Oak Stud is located near some of the world’s leading distilleries.
Meet racehorses at Pin Oak Stud in Versailles.

EAT

12:15 p.m. – 1:15 p.m.

Enjoy lunch at one of Central Kentucky’s favorite local spots, Wallace Station Deli and Bakery. Wallace Station is owned by Ouita Michel, a famed Kentucky chef known for her emphasis on locally-sourced ingredients and farm to table meals. Located in the heart of Horse Country on the scenic Old Frankfort Pike, and just a few minutes from Pin Oak Stud, Wallace Station is a must-visit stop when touring the Bluegrass.

Wallace Station is located on scenic Old Frankfort Pike, in the heart of Horse Country.
Enjoy a locally-sourced meal at Wallace Station Deli and Bakery in Midway, Kentucky.

TOUR

1:30 p.m. – 2:45 p.m.

Meet mares and foals at Pin Oak Stud’s nursery division, located on Old Frankfort Pike in Midway. Guests will have the chance to pet and feed peppermints to momma mares and young horses, the future athletes of Pin Oak’s racing stable. Throughout the tour, the expert tour guide will provide insight on how racehorses are raised, and why Kentucky is widely considered the best place in the world to raise these horses.

The Pin Oak Stud Nursery Experience is offered most days at 1:30 p.m., learn more and plan your visit by clicking here.

The Pin Oak Stud nursery division is home to mares, foals and yearlings.
Meet momma mares and young foals at Pin Oak Stud’s nursery division.

EXPLORE

3 p.m. – 5 p.m.

Visit one of Kentucky’s most famed distilleries, Woodford Reserve, to learn about the process of crafting Bourbon, from fermentation to distilling to bottling, and every step in between. Woodford Reserve’s stunning campus is the setting for a fascinating tour, with opportunities to experience a guided tasting or enjoy a craft cocktail.

Learn more and book a visit of Woodford Reserve by clicking here.

Explore the grounds of Woodford Reserve with a guided tour.
Enjoy a guided Bourbon tasting at Woodford Reserve Distillery in Versailles, Kentucky.

Note: This itinerary is a suggestion only and is based on a sample of what tours may be available summer and fall of 2026. Each Horse Country tour requires that guests be ticketed in advance. Tickets are available for purchase at www.visithorsecountry.com or by calling 859-963-1004. Though this info has been researched & is being shared in good faith, tour availability is subject to change.

Day Trip Itinerary: Diamond A Farm and Castle & Key Distillery

Central Kentucky is a region known for producing the world’s best racehorses and Bourbon. Some of the world’s top horse farms and distilleries sit among the rolling hills of the Bluegrass. Follow this itinerary for a full day exploring Kentucky’s Horse Country, including an interactive horse farm tour, locally-sourced meal and distillery tour.

This itinerary is based off of tour offerings in Summer and Fall of 2026.

TOUR

10 a.m. – 11:30 a.m.

Meet momma mares and young foals on a tour of Taylor Made at Diamond A Farm in Versailles. This highly interactive tour takes guests behind-the-scenes of a leading Thoroughbred breeding operation, with many opportunities to pet and feed horses. Throughout the tour, guests will learn about the fascinating world of Thoroughbred breeding and racing, and have the chance to meet leading broodmares and their offspring.

Tours of Taylor Made at Diamond A Farm are offered daily at 10 a.m., 12 p.m. and 2 p.m, which can be booked by clicking here.

Taylor Made at Diamond A Farm is located near some of the world’s leading distilleries.
Meet young Thoroughbreds at Taylor Made’s Diamond A Farm in Versailles.

EAT

12 p.m. – 1 p.m.

Take the backroads to The Stave, a beloved Kentucky eatery located in the heart of Horse and Bourbon Country! The Stave is just a few minutes from major distilleries like Castle & Key, Woodford Reserve, and more, along with horse farms like Taylor Made at Diamond A Farm and Pin Oak Stud. The Stave utilizes locally-sourced ingredients to elevate classic Kentucky favorites, like pimento cheese, burgoo, fried chicken, and more.

Take the backroads to enjoy classic horse farm views, including farms like Pin Oak Stud.
The Stave is a beloved Kentucky restaurant, located near leading horse farms and distilleries.

EXPLORE

1:30 p.m. – 3:30 p.m.

Visit one of Kentucky’s most unique distilleries, Castle & Key, located in Frankfort, Kentucky, just a short drive from Versailles, Kentucky. Castle & Key’s distillery is set against a stunning backdrop of gardens and historic architecture. Guided tours of the property are offered daily, providing a fascinating look at their spirits and facility.

Learn more and book a visit of Castle & Key by clicking here.

Castle & Key offers tours daily. Photo courtesy of the Kentucky Bourbon Trail®.
Explore the stunning, historic grounds of Castle & Key Distillery in Frankfort, Kentucky. Photo courtesy of the Kentucky Bourbon Trail®.

Note: This itinerary is a suggestion only and is based on a sample of what tours may be available summer and fall of 2026. Each Horse Country tour requires that guests be ticketed in advance. Tickets are available for purchase at www.visithorsecountry.com or by calling 859-963-1004. Though this info has been researched & is being shared in good faith, tour availability is subject to change.

Day Trip Itinerary: Horses and Bourbon in Louisville, Kentucky

Kentucky is known worldwide for horses and Bourbon, and the Louisville, Kentucky area combines the best of both. Follow this itinerary for a full day exploring Kentucky’s Horse Country, including visits with retired racehorses, and the Kentucky Bourbon Trail®, with a distillery tour and more.

This itinerary is based off of tour offerings in Summer and Fall of 2026.

TOUR

11 a.m. – 12 p.m.

Experience the tranquility of horses being horses at the Thoroughbred Retirement Foundation’s sanctuary farm at Chestnut Hall. Located in Prospect, about 15 miles from Louisville, the farm is home to a herd of retired racehorses. When visiting TRF at Chestnut Hall, guests will have the chance to get hands on with the horses, feeding peppermints and petting them while learning about their stories, from the racetrack to retirement.

Tours of the Thoroughbred Retirement Foundation at Chestnut Hall are offered daily at 11 a.m., which can be booked by clicking here.

Enjoy the tranquility of a horse farm, just a short drive from downtown Louisville, Kentucky.
Get up close and personal with retired racehorses at Chestnut Hall in Prospect, Kentucky.

EAT

12:15 p.m. – 12:45 p.m.

Grab lunch between tours at Market on 42 in Goshen. Just a five minute drive away from both Chestnut Hall and Second Stride, this locally-owned market sources many of their goods from local farms. Grab a freshly made sandwich and enjoy lunch on the porch!

Enjoy a locally-sourced sandwich from Market on 42.
Market on 42 is located in the historic Goshen Store.

TOUR

1 p.m. – 2 p.m.

Get an inside look at how racehorses become riding horses with a tour of Second Stride in Prospect, Kentucky. Second Stride retrains Thoroughbreds for second careers as riding horses, providing them with the foundation and skills to succeed in a variety of disciplines, including jumping, dressage, barrel racing and so much more. When touring Second Stride, guests will learn about the retraining process and have the chance to meet some of the horses in training. Plus, say hello to the Second Stride ambassador horses – Kentucky Derby contender Twinspired and graded stakes winner Warrior’s Club.

Tours of Second Stride are offered every weekday at 1 p.m., and can be booked by clicking here.

Meet retired racehorses at Second Stride in Prospect, Kentucky.
Learn how racehorses are trained to be riding horses at Second Stride.

EXPLORE

After your tour of Second Stride, take a short drive to Louisville to experience Kentucky’s Bourbon culture! Immerse yourself in the Bourbon industry with a tour of Angel’s Envy, a fully-operational distillery located in Downtown Louisville. Get an inside look at how elite Bourbon is distilled and bottled, with the chance to enjoy a taste of Angel’s Envy at the conclusion of the tour, responsibly, of course! Tours of Angel’s Envy are booked daily, and you can learn more by clicking here.

Continue the fun with a visit to the Frazier Museum, an official welcome center for the Kentucky Bourbon Trail® and a museum highlighting all things Kentucky, from the state’s history to its culture, and more. For sports fans, we highly recommend a visit to the Louisville Slugger Museum, which offers factory tours and engaging exhibits about the history of baseball. Learn more about what Louisville has to offer from Go To Louisville.

Angel’s Envy Distillery is located in downtown Louisville. Photo courtesy of the Kentucky Bourbon Trail®.
Learn more about America’s Native Spirit at the Frazier Museum. Photo courtesy of the Kentucky Bourbon Trail®.

Note: This itinerary is a suggestion only and is based on a sample of what tours may be available summer and fall of 2026. Each Horse Country tour requires that guests be ticketed in advance. Tickets are available for purchase at www.visithorsecountry.com or by calling 859-963-1004. Though this info has been researched & is being shared in good faith, tour availability is subject to change.

Day Trip Itinerary: Lane’s End Farm and Bluegrass Distillers

Enjoy a day combining the best of Kentucky’s Horse Country and the Kentucky Bourbon Trail with a visit to Lane’s End Farm and Bluegrass Distillers at Elkwood Farm. See champion stallions and meet mares & foals before getting an inside look at how Kentucky bourbon is distilled and bottled.

This itinerary is based off of tour offerings in Summer and Fall of 2026.

TOUR

Sitting on 2,300 acres, Lane’s End Farm is one of Kentucky’s leading Thoroughbred breeding operations. During this experience guests will get a tour of the stallion complex and learn about the rich history of the farm. Their stallion division is home to champions such as Flightline, Candy Ride, Liam’s Map, and Union Rags. Guests will learn about each stallion’s race record, pedigree, and progeny. A handful of stallions will be brought out for guests to view, similar to showings for clients assessing which stallions they might breed to their mares.

The Lane’s End Farm Stallion Tour is offered six days a week at 10 a.m., which can be booked by clicking here.

The stallion tour at Lane’s End Farm Versailles, Kentucky
Honor A.P. at Lane’s End Farm in Versailles, Kentucky

TOUR

Stay for the Lane’s End Shuttle Tour for a well-rounded experience at this famed farm. The shuttle experience takes guests to see the nursery division, where they could meet mares and foals, yearlings and retired broodmares. This tour is interactive for guests to get hands on with mares and foals. Among their retired mares is the famed Zenyatta, who is now retired from racing and breeding.

The Lane’s End Farm shuttle experience is offered six days a week at 11:30 am. This tour can be booked separately by clicking here.

The shuttle tour of Lane’s End Farm in Versailles, Kentucky
The shuttle tour of Lane’s End Farm in Versailles, Kentucky

EXPLORE

After spending the morning at Lane’s End Farm, head to lunch at the Brown Barrel in downtown Midway. It is named in honor of Winston Eugene Peace who made bourbon barrels for more than 25 years. One of their most notable dishes is the classic Kentucky hot brown. They also offer a nice selection of bourbon for sale to complete Kentucky experience.

Click here to check out their website and learn more.

The Brown Barrel is 10 minutes (5.4 miles) from Lane’s End Farm.

The Brown Barrel in Midway, Kentucky
The Brown Barrel in Midway, Kentucky

EXPLORE

After lunch, head over to Bluegrass Distillers at Elkwood Farm. They were founded in 2012, starting the operation in Lexington before moving to Elkwood Farm in Midway. Bluegrass Distillers is a small batch distillery that hand mashes their grain, which has earned their spirits national recognition. They offer tours and tastings and be sure not to miss their feature Bourbon and Chocolate Pairing Tasting!

Bluegrass Distillers offers tours from 9:00 am to 4:30 pm every hour, 7 days a week. Click here to check their schedule and book a tour.

Bluegrass Distillers is located 12 minutes (6.6 miles) from Lane’s End Farm.

Bluegrass Distillers at Elkwood Farm in Midway, Kentucky.
The stunning Elkwood Farm, home to Bluegrass Distillers.

Note: This itinerary is a suggestion only and is based on a sample of what tours may be available summer and fall of 2026. Each Horse Country tour requires that guests be ticketed in advance. Tickets are available for purchase at www.visithorsecountry.com or by calling 859-963-1004. Though this info has been researched & is being shared in good faith, tour availability is subject to change.

Kentucky: The Land of Horses and Bourbon

Experience the best of both in Central Kentucky, from world class bourbon distilleries to breeding farms. Woodford County, Kentucky is home to some of the best Thoroughbred breeding farms in the world, and is a part of Kentucky’s renowned bourbon country. Learn more about what makes this area so special, and find out why it is home to the best racehorses and best bourbon.

This itinerary is based off of tour offerings in Summer and Fall of 2026.

Saturday

TOUR

Start your morning with a tour of Taylor Made at Diamond A Farm in Versailles, Kentucky. This storied farm has a rich history of horses and bourbon, and was once home to legends like Cigar, Azeri and more. Today, the farm is home to top broodmares like Spice is Nice, whose son Renegade was second in the 2026 Kentucky Derby. This immersive experience showcases a leading Thoroughbred nursery farm, and provides guests with the special opportunity to pet and feed mares and foals.

Taylor Made at Diamond A Farm offers tours daily at 10 a.m., which can be booked by clicking here.

Diamond A Farm in Versailles sits next to the famed Woodford Reserve Distillery.
Get up close and personal to mares and foals on a tour of Taylor Made at Diamond A Farm.

EXPLORE

Visit Woodford Reserve Distillery, just a few minutes from Taylor Made at Diamond A Farm. Woodford Reserve offers immersive tours and tastings that provide a unique insight into the world of Bourbon. Even if you don’t have time for a tour, we highly recommend visiting the gift shop to grab a drink from the bar and pick up a bottle of Bourbon or another gift to commemorate your time in Kentucky. As always, be sure to enjoy responsibly, and check out our friends at the Kentucky Bourbon Trail for more details about Bourbon tours in Kentucky.

Woodford Reserve is located 2.4 miles (about a 4 minute drive) from Taylor Made at Diamond A Farm.

Bourbon barrels at Woodford Reserve in Versailles, Kentucky.
Tastings at Woodford Reserve in Versailles, Kentucky.

Sunday

TOUR

Enjoy a shuttle ride through a stunning horse farm and learn more about a worldwide breeding and racing operation with a tour of Godolphin’s Gainsborough Farm. Gainsborough Farm is home to momma mares and baby foals, including some of Godolphin’s top broodmares. Kentucky Derby winner Sovereignty was born and raised on this farm!

Godolphin at Gainsborough Farm offers tours at 10 a.m. + 1 p.m. on Thursdays, Fridays, Saturdays and Sundays.

Gainsborough Farm is located about 3.5 miles (8 minutes) from Woodford Reserve Distillery

Meet mares and foals at Gainsborough Farm in Versailles.
Meet future champions at Godolphin’s Gainsborough Farm in Versailles.

EXPLORE

Bluegrass Distillers is another Woodford County distillery with a unique approach to bourbon. They were founded in 2012 in Lexington, before moving to their current location in Midway, Kentucky in 2020. Bluegrass Distillers is a small batch distillery that hand-mashes their grain, which has earned their spirits national recognition. They offer tours and tastings on most days, including a can’t-miss Bourbon and Chocolate Pairing Tasting!

Bluegrass Distillers is located 8.3 miles (about 13 minutes) from Gainsborough Farm.

Bluegrass Distillers at Elkwood Farm in Midway, Kentucky.
The stunning Elkwood Farm, home to Bluegrass Distillers.

EXPLORE

After your day of horses and bourbon, head to the charming town of Midway for dinner and shopping. This historic town has even been featured in Hallmark movies! Enjoy dinner at local favorites like Holly Hill Inn, Brown Barrel, Goose and Gander and more, or drive a few more miles into Horse Country to stop at the famed Wallace Station.

Visit the Midway Museum or one of the many stores in charming downtown Midway, Kentucky.
Enjoy dinner at Wallace Station Deli and Bakery in Midway, Kentucky.

Note: This itinerary is a suggestion only and is based on a sample of what tours may be available summer of 2026. Each Horse Country tour requires that guests be ticketed in advance. Tickets are available for purchase at www.visithorsecountry.com or by calling 859-963-1004. Though this info has been researched & is being shared in good faith, tour availability is subject to change.