May 3rd

Gator Stompin’ 2018 | Downtown and Midtown Gainesville | May 3 – 4 

The Gator Stompin’® pub crawl and music festival has been a rite of passage in Gainesville for over 30 years. At the end of every Spring semester, thousands of people come together to celebrate being part of the Gator Nation. Ticket prices vary.

May 4th

First Friday Art Walk | Downtown Ocala | 6 PM-9 PM

Every year, the First Friday Art Walk occurs from 6 PM-9 PM on the first Friday of every month from September until May. Located within Ocala’s historic downtown, event festivities include over 40 artist’s displays, acoustic entertainment, free family art activities, and extended shopping hours.

Marion in May Exhibit | Marion Cultural Alliance | 6 PM-9 PM

Join the Marion Cultural Alliance for May’s exhibit, “Marion in May”. On view will be a unique expression of art inspired by our country’s rich and vibrant charm, throughout the month of May. Don’t miss this beautiful exhibit!

Couch Sessions Series: Feat. Musician Becky Sinn & Artist Mel Fiorentino | Historic Taylor House | 8 PM

Musician and lyricist Becky Sinn will be performing and sharing the behind-the-scene process of creating original music whilst lounging on an art piece painted by Artist Mel Fiorentino. Fiorentino, a critically-acclaimed Ocala-based artist, will be painting LIVE throughout the evening. Find more about ticket types. Ages 18+ only.

May 5

WE Clinic and Schooling Show | Florida Horse Park | May 5 – 6

Hosted by Southeast Baroque Horse Shows and HWalters Dressage LLC this clinic/schooling show for WE at Florida Horse Park offers clinics on May 5-6 with the show being held the 6th. Clinicians are Ruth Perez and Heather Walters, bringing knowledge from multiple disciplines and a judges view.

The Art of Riding LLC and SBHS is hosting this Benefit schooling Dressage Show in honor of Juan Ledgard! All profits will be donated towards his horses and any care. Come enjoy competing and support a great cause in his memory.

Ocala Downtown Market | Downtown Ocala | 9 AM – 2 PM
Come out to enjoy a celebration of local produce, crafts, and food trucks! Just around the corner from the square, the open-air market pavilion hosts a wide variety of local and regional vendors offering unique and quality products.
3rd Annual Ocala Pet Expo | Jervey Gantt Park & Letty Towles Dog Park | 10 AM – 2 PM

Enjoy a paw-itively fun day with your pet at the park with food, vendors, contests and prizes. Visit the animals for adoption, take in the agility demonstrations, and meet Molly, the gentle ambassador of Marion County’s animal abuser registry! Don’t forget a donation for the pet food drive and to try your luck in the contests for Cutest Pet, Best Trick or Talent! FREE admission!

PACE Derby Day 5K, 10K, & 1-mile Fun Run | Florida Horse Park | May 5

PACE Center for Girls, and Great American Insurance Group-Equine Division, present the Annual Derby Day 5K, 10K, and 1-mile fun run.  Participants can run, walk and jog through the beautiful Florida Horse Park on the morning of the Kentucky Derby. The 10K route also takes runners through the Florida Greenway trails. Complimentary mint julep “mocktails” help participants cool down and refresh after the race. Ribbons are given for the top three places, and the overall winner of each division has their picture made while they are draped in a garland of roses.

Derby Day at Katya Vineyards | Katya Vineyards | 2 – 11 PM

Head to Katya Vineyards to watch and celebrate the 144th Kentucky Derby! Grab your best Derby Hat and enjoy a Derby Day Themed Menu and wine pairings whilst watching the race on our HD TVs.

9th Annual La Plaza Grande Art & Craft Festival | La Plaza Grande, Lady Lake| March 5-6 

There’s something for everyone at this craft festival, featuring arts and crafts. Handmade one-of-a-kind jewelry pieces, personalized wall hangings, art for your pets, ceramics much more. This two day event has no admission fee!

May 8th

Women’s Council of Realtors Member Mixer | The Salted Brick at Trilogy at Ocala Preserve | 4:30 – 6:30 PM

Attend the Women’s Council of REALTORS of Ocala/Marion County & Gainesville Networking Mixer for the opportunity to mingle and meet empowering women within the real estate industry. RSVP online.

May 11th

The Southern Drive | Grand Oaks Resort | May 11 – 13

The Southern Drive at Grand Oaks is an American Driving Society (ADS) Southeast Region Recreational Driving weekend with lots of fun and interesting activities planned. This three-day event features driving derby tournaments, clinics and more. Competitor signups are available via the event site. Come out and cheer your favorite performer.

Sunshine Region Pony Club Show Jump Rally | Florida Horse Park | May 11 – 13 | 8 a.m. – 5 p.m.

The Sunshine Region, part of the United States Pony Club, is composed of 14 clubs and one riding center in Florida, southern Georgia and the U.S. Virgin Islands. USPC is one of the leading junior equestrian organizations in the world, represented throughout 30 countries. Attend the 2018 SRPC Show Jumping Rally at the Florida Horse Park available for both qualifying and non-qualifying riders.

After Dark in the Park Movie Series | Webb Field at Ed Crosby  | 8:30 PM

Bring your little ones to watch the Lego Batman Movie at, this event is FREE and open to the public. Popcorn and drinks will be available for purchase. Please bring your own lawn chairs and blankets.

2018 Gala: An Evening at the Moulin Rouge | Golden Ocala Golf and Equestrian Club | 6 PM

Benefiting the Ocala Symphony Orchestra and Reilly Arts Center, enjoy an evening of live music, featuring Michael and Angela Ingersoll, critically acclaimed Chicago-based performers featured on The Tonight Show, Oprah and more! Expect a full dinner, open cocktail hour, dancing, French-themed escapades and a silent and live auctions.

Remembering John Denver, a Tribute starring Ted Vigil | Reilly Arts Center | 7:30 PM

Remembering John Denver, a Tribute starring Ted Vigil’s performance of “Take Me Home Country Roads, Leaving on a Jet Plane, Rocky Mountain High” and more of John Denver’s greatest hits. Tickets starting at just $10

– “Watching Ted perform, you might be convinced that John Denver never died! His look and sound are scary!” -Las Vegas Review Journal

May 12th

WindFM Rocks the Reilly: Wall of Echos | Reilly Arts Center | 7:30 PM

Join WIND-FM as Wall Of Echoes performs as the ultimate Pink Floyd Tribute. Playing in large venues and festivals, Wall Of Echoes dedication to note for note performance and show is unparalleled by any other tribute band.

Jazz on the Vineyard Green | Lakeridge Winery & Vineyards, Clermont | 10 AM – 5 PM

Enjoy talented Jazz musicians on the outdoor stage the entire weekend. Lakeridge wine, beer, soft drinks and a variety of food is available for purchase, along with complimentary Winery tours and wine tasting.

May 13th

M.O.M.S. Day 5K Run/Walk 2018 | Jervey Gantt Park | May 13

Whether you are participating WITH your Mom, In HONOR of your Mom, or PRIVILEGED to be a Mom all are welcome to walk, jog or run this 5k.  All proceeds benefit Memories of Missing Smiles, Inc. (M.O.M.S.) Children’s Memorial Park and Reflection Pond A 501c3, non-profit org. dedicated to Remembering the Lives and Smiles of our children who have died.

FAFO Presents The Symphony Under The Stars | Ocala Golf Club | 4 PM

Join the Fine Arts For Ocala for their annual Symphony Under the Starts. Gates open at 4 p.m. enjoy live music and fireworks.  Be sure to bring your own picnic or purchase food, beer or wine from hand selected vendors. Pre-sale and VIP tickets are available through the website.

Mother’s Day Tour | Carson Springs Wildlife Conservation Foundation, Gainesville | 1 – 3 PM

Celebrate Mother’s Day with animal mothers and their babies! A special Mother’s Day event will be held from 1pm-3pm including tours of the Conservation, roses for mothers and refreshments for all. Be sure to check out the newly-born baby hyena, caracal and lemurs. Proceeds benefit the animals of the Conservation and their care needs.
Admission is $30, for adults $10 teen 18 and under. *Reservations required email*

May 17th

Live On Stage: “Mamma Mia!” | Ocala Civic Theatre | Times Vary

The irresistible ABBA musical “Mamma Mia!” is live on stage May 17 – June 17, this fabulously fun musical is full of ABBA’s greatest hits, with plenty of catchy, upbeat tunes like “Dancing Queen,” “Money, Money, Money,” “Waterloo,” and “Mamma Mia!”. Tickets are $28 for adults and $12 for full-time students (school ID required for college students). Group rates are available – make it a girls’ night out! For more information, call (352) 236-2274 or go to

May 18th

Brick City Blues Fest: Soulsville USA! | Reilly Arts Center | 7 PM

A Tribute to the sweet sounds of American Soul Music with live performances by Little Jake & The Soul Searchers, Rondo & The Mojo Downs Band, Sheba The Mississippi Queen and The Reverend Billy C. Wirtz.  All proceeds benefit Ocala Outreach Foundation’s “Feed the Need” Project.

Battle of the Badges Basketball Tournament | Trinity Catholic High School | May 18 & 19

Law enforcement officials will compete in a Battle of the Badges basketball tournament at Trinity Catholic High School, on May 18 and 19. Admission is $5, and all proceeds will go to the Chris Uhle Scholarship Fund.

Partners of the Park XC Schooling and 3-phase Show | Florida Horse Park | May 19 – 20 

Partners of the Park is a volunteer organization of equestrians and equestrian enthusiasts dedicated to delivering a variety of schooling, dressage, and hunter-jumper shows for riders and spectators alike. Profits go toward building a better horse park for everyone to enjoy.

May 19th

Marion County Food & Wine Experience | Paddock Mall | 12 – 5 PM

The Paddock Mall will be hosting its first annual Marion County Food & Wine Experience where local restaurants will be offering decadent samples of food featured throughout Marion County paired with live music, a fashion show, and more!

American Craft Beer Week | Infinite Ale Works | 12 – 5 PM

Celebrate American Craft Beer Week at Infinite and experience their newest creation and other Central Florida Breweries on guest taps!

May 20th

Ocala Style Women’s Expo | College of Central Florida Klein Center | 12 – 5 PM

Come enjoy an empowering day of food, fun, shopping and inspiration for today’s woman. Browse vendors and charity education areas while enjoying food, dessert and drink tastings.  Attendees will have the opportunity to hear empowering speakers, interact in a women-led panel discussion and meet inspirational local celebrities.  Tickets are $5, proceed benefit Ignite For Ocala.

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Take a look at these additional resources for even more local activities and events in our area.