Kentucky Derby Museum’s Annual Hat Fashion Show is a signature spring event celebrating the artistry, fashion and tradition of Derby style. Each year, the Hat Show brings together stylish vendors and a lively social atmosphere—making it a can’t-miss experience for ladies! Featuring exclusive designs for both women and men from the Museum’s celebrated featured milliners, the KDM Hat Show is your chance to get inspired and shop one-of-a-kind pieces—all in one unforgettable event. In addition to The Fashion Show, there is also delicious food, drink and featured Derby merchandise for sale!
Day 1: Saturday, March 20, 2027
Today we travel to LaGrange, Kentucky, – soundfamiliar? Yes, it was the site of the two-day 2025Girls Mystery Tour. Our local guide will join us at the Windy Meadows Equestrian and Event Center (featured in Hallmark’s Kentucky Roses Derby movie, May 2, 2026) where we’ll enjoy lunch in the elegant gathering space overlooking rolling pastures and thoroughbred country scenery. Following lunch, we’ll enjoy a guided tour of Windy Meadows with Ellie, learning about the daily life, care, and training of the farm’s horses. The experience captures the quieter, more personal side of Kentucky’s horse industry that most visitors never get to see. We’ll then take a beautiful drive to Knock on Wood, a boutique located in Oldham County in the historical river port town of Westport where we will find this quaint gift shop featuring a wide variety of home décor and seasonal touches, ladies clothing, purses, jewelry, and bath and body products. (A huge hit on the 2025 Girls Mystery Tour). We then depart to check into our lodging for the night Drury Inn and Suites Louisville, where their Kick Back Dinner will be served. (L, D)
Day 2: Sunday, March 21, 2027
Today is the BIG event! Following breakfast at the hotel, we will attend the Kentucky Derby Museum’s Annual Hat Fashion Show! We’ll see a Runway Showcase where we get a firsthand look at the season’s most stunning hat and jewelry. Then, explore exclusive shopping opportunities with milliners and a curated selection of vendors. On our way home, we will stop at beautiful Huber’s Winery and Farm for a delicious lunch. (B, L,)
Your VIP Ticket Includes:
• Complimentary Spirits as well as soda, coffee, and non-alcoholic drinks.
• Brunch Bites, a delicious spread of appetizers
• Lively Atmosphere: A DJ will keep the energy high, ensuring an unforgettable experience.
• Front Row Fashion Show seats
• SWAG bag full of goodies!
INCLUDES:
• Windy Meadows tour and delicious lunch
• Shopping at Knock on Wood
• 1 night accommodations/luggage handling at Drury Inn and Suites Louisville
• Kick Back Dinner at Drury Inn
• VIP Ticket to Kentucky Derby Museum’s Annual Hat Fashion Show
• Lunch at Huber’s Winery and Farm
• Deluxe motorcoach transportation/driver’s gratuity
• Fully escorted by Jane’s Journeys
PRICE PER PERSON:
DOUBLE: $799
TRIPLE: $749
QUAD: $718
SINGLE: $987
$300 deposit with reservation.
Final payment due December 29, 2026.
Trip Protection is recommended and available for
purchase: $56 per person double; $52 per person
triple; $50 per person quad; $69 per person single.
Trip Protection payment due with deposit. Trip
Protection price subject to change.