The summer officially bowls off in Jamaica with a white-ball series against Sri Lanka from June 3–14, featuring three One Day Internationals and three T20 Internationals. Fans are encouraged to secure their tickets via tickets.windiescricket.com and be part of what promises to an exciting and thrilling summer of cricket.
Mark your calendars and lace up those sneakers—Tru-Juice 5K Run/Walk is back for its 11th staging and better than ever! Join us for a day of energy, unity, and purpose in the lush surroundings of the Tru-Juice Orchards.
Come for the run, stay for the cause—and be a part of something meaningful. Let’s move together for health, community, and impact. We can’t wait to see you there!
National Stadium. This is trials for our Jamaica track and field athletes to vie for a spot on Team Jamaica for upcoming world events including PanAm, World Championships and NACAC. Held at the National Stadium in Kingston & St. Andrew www.trackandfieldjm.com
The Everyone's A Winner / The Best Dressed Chicken 3K & 5K returns on Father's Day, Sunday, June 21 to roll out the red carpet for all fathers on their special day. The backdrop for the Everyone's A Winner / The Best Dressed Chicken 3K & 5K is the scenic Hope Botanical Gardens.
The 27th Jamaica Observer Table Talk Awards is a celebration of the joy of food. The Jamaica Observer Food Awards is now one of the most anticipated food events in the Caribbean. This annual festival recognizes excelence in food creation, food service and event decor among others.
www.jamaicaobserver.com Location: Devon House
The Jamaica Legion National Poppy Appeal 5K Run/Walk 2026 is scheduled to take place on Sunday, June 28, 2026, commencing at 6:00 a.m. at Up Park Camp. This event forms part of the annual National Poppy Appeal Jamaica, an established fundraising initiative organized by the Jamaica Legion to support military veterans, widows, and their dependents.
An exciting party staged by Murray’s Fish and Jerk Hut at Appleton Estate Farm in St. Elizabeth. This event will provide you with a truly unique Jamaican party experience like no other. Contact for tickets: https://caribtix.com/buy-tickets
Once a year, in start July, Jamaica holds the International Reggae Festival. Jamaica is known as the motherland of the rhythmical unique music – the Reggae. The event takes place in Kingston, the capital of Jamaica, which is located in south east of the island near a charming bay.
Due to the numerous visitors during the festival day and the high demand for accommodations it is recommended to check hotel rates and book rooms well in advance. The International Reggae day hosts dozens artists, local and foreigners, in a marvelous music marathon. Lot of artists comes from the Caribbean Islands.
Kingston Kitchen is Jamaica's premier Caribbean food market — where foodie crews, families, and friends come together over the best plates the island has to offer. From jerk to dessert, from local artisans to beloved vendors, every bite tells a story.
The tournament is one of The Heart Foundation of Jamaica’s (The HFJ) major fund-raising events each year.
The late Vic Higgs had served on the Board of the Foundation for many years and was well known in golfing circles, having assisted the Jamaica Tourist Board in the staging of the Johnny Walker World Golf Tournament.
The tournament was started in 1992 when the Friends of the Foundation as well as enthusiastic golfers decided that a Tournament bearing Higgs’ name would be appropriate to keep his memory alive.
Constant Spring Golf
Venue- Alligator Pond, Manchester. The event will feature a wide array of seafood dishes and will culminate after a day of fun with a carnival type concert and party on the beach. The event usually attracts over 10,000 patrons. www.littleochie.com
Dream Weekend 2026 is the Caribbean’s ultimate summer party experience, set to take over Montego Bay from July 30 to August 3, 2026. This iconic week-long festival brings together world-class DJs, top dancehall and international artists, and a series of high-energy themed events across multiple premium venues.
Marking a bold new chapter, the 2026 staging introduces bigger spaces, enhanced production, and an elevated entertainment experience—delivering nonstop music, culture, and unforgettable vibes in Jamaica’s tourism capital. For more information, visit https://dreamwknd.com/
Reggae Sumfest is Jamaica's premier festival dedicated to showcasing our island's indigenous reggae music while also promoting Jamaica as a prime summer destination. Reggae Sumfest attracts visitors and media from all across the globe. The 2026 festival will mark the 34th annual staging of this event. It's new tagline is: Our Music Our Festiival
Email: www.reggaesumfest.com
The Denbigh Show is the oldest, largest and most dynamic Agricultural Show in the English Speaking Caribbean and one of Jamaica's most iconic event that was held for the first time in 1952 and since then as reminded us each year of what we have achieved in agriculture and its related sectors.
Emancipation Day in Jamaica, observed on August 1, honors the end of slavery in 1834 and celebrates the resilience of ancestors, forming part of a week-long cultural celebration leading up to Independence Day.
The 2026 edition of Come Alive is scheduled for Emancipation Day, August 1, 2026, at the iconic King’s House East Lawns in Jamaica. This national worship event is designed to inspire, uplift, and unite attendees in a collective celebration of faith and freedom, continuing the tradition established by the 2025 concert which drew over 15,000 patrons and raised significant funds for charitable causes.
Independence Day is the national day of Jamaica, celebrated in annually on 6 August, the anniversary of the coming into force of the Jamaica Independence Act 1962. It is one of the most senior public holidays in Jamaica.
The Caribbean Premier League (abbreviated to CPL or CPLT20) is an annual Twenty20 cricket tournament held in the Caribbean. It was founded by Cricket West Indies in 2013 to replace the Caribbean Twenty20 as the premier Twenty20 competition in the Caribbean.
The international men’s lacrosse tournament will feature an expected 12 national teams from the Pan-American region and will serve to qualify five teams from the Pan-American region for the 2027 World Lacrosse Men’s Championship in Japan. An additional four teams will earn qualification for the WL Men’s Championship Division II .
History will be made this August as the Kingston Open serves up world-class tennis in Jamaica’s capital, becoming the first ATP Challenger tournament to be staged in the English-speaking Caribbean.
Set against the vibrant cultural backdrop of Jamaica’s bustling city, the Kingston Open will welcome rising international tennis stars competing for valuable PIF ATP ranking points, USD$214,000 ($33.8 million) in prize money, and a pathway to the elite levels of professional tennis.
Plie for the Arts presents Amalgamation – The Global Gala, a world-class dance showcase set to take centre stage at the Little Theatre from August 28–30. This Jamaican-curated international gala highlights the exceptional talent and artistry of the island’s leading dancers in a captivating production that blends technique, storytelling, and cultural expression. Following its Kingston staging, the production will travel to New York and Connecticut, proudly exporting Jamaica’s creative excellence to the global stage. For culture enthusiasts and performing arts lovers, Amalgamation offers a compelling reason to visit Kingston for an inspiring celebration of Jamaican dance, creativity, and international artistic collaboration.
Venue: Little Theatre, Tom Redcam Drive
The Caribbean’s premier pickleball experience returns bigger, louder, and better.
The Jamaica International Pickleball Open 2026 is set for September 11–13 at Pickle & Chill
With international talent, elite competition, island vibes, music, food, and an unmatched atmosphere, JIPO continues to showcase the growth of pickleball in Jamaica and across the Caribbean.
This year the expo will be held in Kingston. A unique networking event developed to showcase Jamaica as a premiere destination for weddings, honeymoons and romance. Jamaica Bridal Expo will bring local and international brides and wedding planners to meet with top destinations, best hotels and services in Jamaica for the bridal market. www.jamaicabridalexpo.com
Jamaica's premier tourism sales and marketing event will be held on Monday, September 14 to Wednesday, September 17 at the Moon Palace Jamaica Hotel in Ocho Rios.
https://www.japex.org/
The CIBC Walk for the Cure 2026 is the Caribbean branch of CIBC’s annual cancer fundraising campaign, designed to support local cancer care organizations and raise awareness about cancer prevention and treatment
Observed annually on the third Monday in October, National Heroes’ Day honours the sacrifices of the seven Jamaicans who helped shape the nation’s path to freedom, self-determination, and progress.
At The Jamaica Reach to Recovery Pink Run, we run not just for ourselves but for every woman, man, and family touched by breast cancer. Together, we raise funds, spread awareness, and stand in solidarity with survivors across Jamaica.
Taste the vibe, feel the rhythm, and live the spirit of Jamaica! There’s no better way to experience the culture of Jamaica than through its rich flavors, music, and community spirit. Come and indulge in the fun and experience Jamaica. Come for the food, stay for the music, and leave with a heart full of Jamaica. Don’t miss it!
Golf, luxury, and breathtaking ocean views come together at the Jamaica Pro-Am 'Annie’s Revenge'—a premier Caribbean golf experience where championship-level play meets signature island hospitality. Set in the vibrant resort city of Montego Bay from November 18 to 22, 2026, this highly anticipated Jamaica golf tournament invites amateur and professional players to tee off against a stunning backdrop of turquoise waters and tropical landscapes. Beyond the fairways, participants enjoy upscale accommodations, lively social events, and the warm welcome that defines Jamaica. For golf enthusiasts seeking a luxury sports getaway in the Caribbean, the Jamaica Pro-Am ‘Annie’s Revenge’ delivers an unforgettable blend of competition, relaxation, and island charm.
All proceeds from the CB Group UWI 5K will go directly towards the development of sports and the education of the most talented and in-need students at The University of the West Indies. Help us develop the next generation of athletes and scholars through your support for the CB Group UWI 5K Run/Walk.
Horse racing excellence. Experience one of the most thrilling events in Jamaica at Caymanas Park, where sport, culture, and family fun unite.
Venue: Caymanas Park, St. Catherine
The Reggae Marathon & Half Marathon is Jamaica’s premier international long-distance race event. Long distance race enthusiasts as well as beginners, have converged in Negril, Jamaica’s capital of casual, for a fun event characterized by good vibes and lots of Reggae music for the past 24 years !
In 2025, the event celebrates its 25th anniversary and moves to Jamaica’s capital, Kingston where enthusiastic supporters come out along the looped, internationally certified course to support participants. Meanwhile, hard working volunteers offer uniquely packaged water and re-hydration fluids at every mile. The pulsating Reggae music on the course also keeps participants in an “irie” spirit, as they burn the mileage.
The Fireworks Festival does more than entertain—it makes a meaningful difference. By supporting local businesses, creating short-term employment opportunities, and attracting visitors from around the globe, the festival contributes to Jamaica’s economic and social growth.