And they’re off!

In Louisville, May always starts with a bang — or, more aptly, with the Kentucky Derby. The annual event takes place on the first Saturday of the month and is easily the most exciting two minutes in sports and the most anticipated day of the year in Louisville. After the race, Louisvillians coast through the rest of May, enjoying Mother’s Day, graduations and Memorial Day weekend in the warmer weather. Here’s a full look at what’s happening around town this month.

Go, baby, go!

April 30 & May 1, 2019: WineFest

The Belvedere at Waterfront Park turns into a regional wine tour both nights of the Kentucky Derby Festival’s WineFest. Some of the area’s 90-plus wineries will have varietals available to sample. Paid admission includes a wine glass, used for tastings throughout the evening, as well as an event pin and a chance to learn about the many varieties of reds and whites from the Bluegrass State and surrounding areas. The event is from 5 p.m. to 9 p.m. on both Tuesday and Wednesday. Tickets are $45, and designated driver tickets are also available at the door for $10.

April 30-May 2, 2019: Dawn at the Downs

Each Derby season, Dawn at the Downs gives locals and out-of-town fans the chance to see the contenders train for the big race while listening to expert commentary. This popular tradition will last from 6:30 a.m. to 8:30 a.m. all three days. Listen while experts announce the horses on the track, evaluate their workouts, discuss past performances and lend insight into this year’s Kentucky Oaks and Derby races. Tickets start at $41 for adults and include a reserved dining seat and breakfast chef’s table.

May 1, 2019: Great Steamboat Race

Always held on the Wednesday before Derby, the Great Steamboat Race pits the venerated Belle of Louisville against the Belle of Cincinnati as the race on the Ohio River. For Louisvillians, this day is the last day you will “work” until the Monday after Derby. Some people get tickets for the boats; others watch from the riverfront. No matter the winner, it’s always fun. Boarding starts at 4:30 p.m. and the race begins at 6 p.m. Belle of Louisville tickets are $150 and include food, drinks and entertainment, while Belle of Cincinnati tickets are $60 and include only the cruise.

May 2, 2019: Pegasus Parade

If there was a bucket list for all things Derby, this would certainly be on it. On Thursday, May 2, the annual free Republic Bank Pegasus Parade is held on Broadway starting at 5 p.m. This family event is a great way to see all the celebrities in town for the Derby. The event is free, but bleacher, chair and VIP seats are available starting at $10. Fun fact: This parade is the oldest event of the Kentucky Derby Festival.

May 2, 2019: Thurby

Thurby is what the Kentucky Oaks used to be to local Louisvillians — a day to call our own without all of the tourists. Thurby offers great racing, specialty bourbon cocktails and a sneak peek at the Derby contenders. It’s a favorite day to go to the track!

May 3, 2019: The Longines Kentucky Oaks

Let’s hear it for the girls! At Kentucky Oaks, fans can watch the fillies race for the lilies the day before Derby. Don’t forget to try the signature drink, the Grey Goose Oaks Lily. Most importantly, don’t forget to wear your pink in support of cancer survivors who will walk in the Kentucky Oaks Survivors Parade.

May 3, 2019: “The Trifecta” Derby Eve Gala at The KFC YUM! Center

Ready to hit “The Trifecta?” This year, the star-studded Derby Eve Gala takes place at The KFC Yum! Center. Walk the red carpet like a celebrity at this black-tie event featuring entertainment by the Grammy Award-winning artist Usher. The Trifecta, an official event of the Kentucky Derby, benefits the West End School and the V Foundation and lasts from 7 p.m. to midnight. Tickets start at $700.

May 3, 2019: Fillies and Stallions at Mellwood Art Center

Fillies and Stallions is entering its 9th year and is no longer Louisville’s best-kept Derby weekend secret. Louisville’s signature celebrity social event is held annually on Derby Eve and features a 40-foot red carpet complete with paparazzi. The music will keep partygoers up late, as this event takes place from 10 p.m. to 3 a.m. To inquire about tickets, visit

May 3, 2019: Unbridled Eve Gala

On Friday, May 3, the Unbridled Eve Gala takes place at the Galt House starting at 7 p.m. This gala is a fundraiser for the Unbridled Charitable Foundation. Watch the stars as they walk the red carpet, and you may even get the chance to mingle with them. Unbridled Eve is co-chaired by the York Sisters, Tonya York Dees and Tammy York Day. For ticket info, visit

May 4, 2019: 41st Annual Derby Breakfast presented by Blade & Bow Bourbon

At the 41st Annual Derby Breakfast, guests will enjoy a Kentucky Proud sit-down brunch by Farm to Fork Catering, open bar featuring presenting sponsor Blade & Bow Bourbon and live bluegrass music from the Misty Mountain String Band. Yard games and garden tours will also be available (weather permitting). The event begins at 9 a.m. and concludes at noon at the Farmington Historic Plantation. Individual tickets begin at $180.

May 4, 2019: The Kentucky Derby

The first Saturday in May is sacred here in Kentucky. The Derby is an experience like no other and nicknamed “the fastest two minutes in sports.” Don’t miss a chance to be a part of the action on Saturday, May 4, and be sure to wear your best frock and hat. Check out our What to Wear article to find out how to do Derby right.

** Take a breath, Louisville. **

May 11 & 12, 2019: Spring Art Show at Mellwood Art Center

Join in on the art celebration at Mellwood Art & Entertainment Center’s Third Annual Spring Art Show. On May 11, from 5 p.m. to 9 p.m., enjoy the preview party with cocktails. On May 12, from 11 a.m. to 5 p.m., support our Kentucky artists! The event is free to enter.

May 17, 2019: Sunset Concert Series at Foxhollow Farm

Each second Friday from May 17 through October 12, Foxhollow Farm in Crestwood opens the farm to friends and neighbors to enjoy music, local food and drinks during its annual Sunset Concert Series. For the family-friendly event, guests are encouraged to bring blankets, chairs, friends, family and even their pets, as long as they are on leashes. Tickets include admission and parking. Savory and sweet treats will be available to purchase from a variety of local restaurants and food trucks, along with craft beer and a bar perched on the farm lawn. Concerts start at 6 p.m., rain or shine. Season passes are $50. Children 12 and under are admitted free of charge, but must have a ticket.

May 13 & 14, 2019: Mother’s Day 5K Run/Walk

Do something different with mom this Mother’s Day. On Saturday, May 13, at 8:30 a.m., celebrate your mom with family and friends by running or walking on the paths of Waterfront Park for the Mother’s Day 5K. There is a rose for every finisher and cake pops waiting for you at the finish line. Don’t forget to bring the kids for the kids’ fun run. Extended registration continues on May 14.

May 18, 2019: Great Strides 5K

The Cystic Fibrosis Foundation of Kentucky and Southern Indiana is hosting the 2019 Great Strides 5K on Saturday, May 18, at Louisville Slugger Field. This is a great way for the community to get involved with a worthy cause and will be filled with family-oriented events, a healthy 5K walk, children’s activities, food and festivities. The suggested fundraising goal for an individual is $300.

May 18, 2018: Walk MS Louisville

Walk MS Louisville 2019 takes place on May 18 at 10 a.m. at Waterfront Park’s Great South Lawn. Walk MS helps the National MS Society of Kentucky and Southeast Indiana team up with friends, loved ones and coworkers to change the world for those affected by multiple sclerosis. Ending multiple sclerosis for good is going to take a team effort, and this walk is one more step in the right direction. There are no fees to participate, but if you raise $100, you get a Walk MS T-shirt.

May 18 through June 12, 2019: Welcome Home Tour & Design Show at Norton Commons

Join Norton Commons for a fabulous tour of 12 stunning, fully furnished geothermal homes, each with unique interiors, for one of the largest home design shows in the region. Centered around the Peppermint Green, a football field-sized civic space, this design show will be open to the public from May 18 to June 2, from noon to 6 p.m. each day. Entry is $15 per person.

May 19, 2019: Clip for Kids at Fourth Street LIVE!

During Clip for Kids, participants raise funds in return for clipping, trimming or shaving their hair in solidarity with kids fighting cancer at Norton Children’s Cancer Institute, affiliated with the University of Louisville. The family-friendly event starts at 1 p.m. at Fourth Street LIVE! and features a fun zone with games, crafts, face-painting, balloon-twisting, shaved ice, giveaways and more. Registration is free with a $25 fundraising minimum.

May 19, 2019: Buy Local Fair

The Louisville Independent Business Alliance will host the 11th Annual Buy Local Fair at Louisville Water Tower Park on Sunday, May 19, from noon until 6 p.m. The event will feature booths from a variety of local businesses, artists, craftspeople, community organizations and farmers, as well as live music, a cooking competition, food and retail vendors, a craft beer tent and a children’s area. This event is free to attend.

May 23-27, 2019: Abbey Road on the River

Celebrate the ’60s at the WAVE 3 News Abbey Road on the River, the world’s largest Beatles-inspired music festival. The five-day event will be held at the Big Four Station Park in Jeffersonville, IN over Memorial Day Weekend and will feature The Cowsills, The Grass Roots, The Buckinghams, Peter Asher & Jeremy Clyde and 50 more amazing bands. Tickets start at $25 for one-day general admission.

May 29, 2019: Waterfront Wednesday

It’s time again for the WFPK Waterfront Wednesday Concert Series. The lineup for May’s free concert on the Big Four Lawn is Dylan LeBlanc, Adia Victoria and Bridge 19. Grab your chairs and blankets, pack a snack, and head down to the riverfront to enjoy an evening of music. The lawns open at 5 p.m.

Have a wonderful May!


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