I Love Stock Island Festival
Festival Schedule
Wednesday
June 11th
Thursday
June 12th
Friday
June 13th
Saturday
June 14th
Father’s Day
June 15th
Wednesday, June 11, 2025
I Love Stock Island Festival Kick Off
Come take a picture in front of the 2025 I Love Stock Island Festival sign! Post your picture with the hashtag #ilovestockisland and show your love for the community
Where: Maloney/MacDonald Ave Grass Triangle
5690 Maloney Ave Key West, FL 33040.
When: All weekend long!
STOCK ISLAND MURAL ART TOUR
Set out on your own artistic scavenger hunt with the Stock Island Mural Art Tour, a captivating exploration of street art and creativity. This self-guided tour allows you to immerse yourself in the rich tapestry of murals that adorn the walls of Stock Island. Find one, find them all! Don’t forget to take a photo, post it and tag us! Remember to include #ilovestockisland
Where: Use the interactive map on the I Love Stock Island website to point you in the right direction so can find all these secret spots!
When: All weekend long!
TASTE OF STOCK ISLAND TROLLEY TOUR & SOS FOOD DRIVE
Board the Old Town Trolley for a culinary tour of Stock Island’s favorite restaurants. At each stop you will enjoy a specially selected small plate and beverage pairing that will be explained by an expert. Each trolley small group is lead by a local tour guide. Bring a non-perishable food item to donate to the SOS Foundation Food Pantry.
Where: Meet at The Perry Hotel, 7001 Shrimp Rd. Stock Island, FL 33040.
When: Wednesday June 11, 2025- 4-8PM.
Thursday June 12, 2025
STOCK ISLAND MURAL ART TOUR
Embark on a vibrant artistic journey with the Stock Island Mural Art Tour, a captivating exploration of street art and creativity. This self-guided tour allows you to immerse yourself in the rich tapestry of murals that adorn the walls of Stock Island. Find one, find them all! Don’t forget to take a photo and include #ilovestockisland #ilovestockisland
Where: Guide yourself with our interactive map on the I Love Stock Island website.
When: All weekend long!
AN EVENING WITH CAYMUS
Join Us for an Exclusive Caymus Wine Tasting Experience, Hosted by Yellowfin Bar & Kitchen at the Luxurious Oceans Edge Resort & Marina
Indulge in an unforgettable evening of elegance and flavor as Caymus Vineyards of Napa Valley showcases a distinguished selection from the renowned Wagner Family portfolio. Savor exquisite wines expertly paired with light, thoughtfully crafted fare prepared by the chefs at Yellowfin Bar & Kitchen.
Guests will also have the opportunity to purchase their favorite vintages and enter a special drawing for the chance to win an exclusive prize.
Space is limited — advanced reservations are required. Secure your spot today for this exceptional tasting experience.
Where: Yellowfin Bar & Kitchen at Oceans Edge Resort & Marina
5950 Peninsular Ave, Key West, FL 33040
When: Thursday June 12, 2025 6pm-7:30pm.
Friday June 13, 2025
STOCK ISLAND HISTORY TOUR
Tour Stock Island in the comfort of Up The Keys’ air-conditioned tour van. In the one-hour tour, passengers learn about Stock Island’s rich history and colorful characters that have allowed for the preservation of the old Florida Keys lifestyle so that it is still present today. Limited space available. Advanced reservations required. Visit the event website to reserve your spot.
Where: The Perry Hotel & Marina, 7001 Shrimp Rd. Stock Island, FL 33040.
When: Friday June 13, 2025- 10AM, 11AM, 1PM
STOCK ISLAND MURAL ART TOUR
Set out on your own artistic scavenger hunt with the Stock Island Mural Art Tour, a captivating exploration of street art and creativity. This self-guided tour allows you to immerse yourself in the rich tapestry of murals that adorn the walls of Stock Island. Find one, find them all! Don’t forget to take a photo, post it and tag us! Remember to include #ilovestockisland
Where: Use the interactive map on the I Love Stock Island website to point you in the right direction so can find all these secret spots!
When: All weekend long!
CAYO HUESO BREWING’S LOW COUNTRY SHRIMP BOIL
Join us at Cayo Hueso Brewing for a flavorful evening at our Low Country Shrimp Boil event! Indulge in a classic Shrimp Boil feast featuring mouthwatering items such as sausage, potatoes, corn, and dessert, all accompanied by a complimentary Cayo Hueso Brewing beer of your choice.
As you savor the delicious spread, take in the sights of the brew house and witness the magic of the shrimp boil as it cooks inside one of our brew kettles. Dinner will be served buffet style in a laid-back atmosphere in the Cayo Hueso Brewing courtyard.
Space is limited, so secure your spot by purchasing tickets in advance. Don’t miss out on this unique culinary experience and join us for a memorable evening of great food, refreshing drinks, fun ambiance at Cayo Hueso Brewing!
Where: Cayo Hueso Brewing
5635 1st Ave. Stock Island, FL 33040
When: Friday June 13, 2025- 5:30pm-9pm
Saturday, June 14, 2025
STOCK ISLAND COLLABORATIVE CLEAN UP
Join us for the Stock Island Collaborative Cleanup in partnership with the First State Bank, Monroe County Sheriff’s Office, Key West City Ploggers, and Oceans Edge Watersport! This community-driven event aims to restore and preserve the natural beauty of Stock Island, while fostering a sense of environmental responsibility. Together, we will gather at designated locations and work hand in hand to remove litter and debris from the island’s shores, parks, and public spaces. By joining forces with the brave law enforcement officers from all over Monroe County and the Ploggers of Key West for our land based clean ups, and Oceans Edge Watersports for our water-based clean-up, we can make a meaningful impact on the local ecosystem. Let’s come together, protect our environment, and create a cleaner, healthier Stock Island for all to enjoy.
Oceans Edge Water Sports– Departing from 5950 Peninsular Ave at 8am-11am- Call to reserve –786-862-6317
Land Based Clean Up Hosted by Oceans Edge Resort and Marina, 5950 Peninsular Ave- Check in at 7:45am for a brief meeting and grab your supplies. Clean up is 8am-11am. Join us back at the Oceans Edge Watersport Tiki Hut for the to dispose of the collected trash.
Key West City Ploggers – Departing from the corner of US1 and College Road near Cow Key Bridge at 8am-11am
FATHER SON HAIR CUTS
Visit Beards and Brews Barbershop & Bar for Father-Son Haircuts. Get Dad ready to look and feel his best on Father’s Day with an amazing hair cut and barber service from the amazing staff at Beards and Brews! Pay for Dad’s haircut and get your son’s haircut for free! And don’t forget to come a little early and enjoy a beverage at the bar while you wait! This is sure to be great Father-Son bonding time during the I Love Stock Island Festival
Where: 5450 MacDonald Ave Unit 6. Key West, FL 33040.
When: Saturday June 14, 2025- Call ahead to schedule your appointment. (305) 292-1460.
I LOVE STOCK ISLAND FESTIVAL FOR THE FAMILY
Mark your calendars for the MAIN EVENT! The 3nd annual I Love Stock Island Festival for the Family! This lively celebration will be filled with fun and excitement for everyone. An artisan market, delicious food and drinks, activities for kids, entertainment, and a silent auction just to name a few. This community event is free of charge but come prepared buy raffle tickets and to place a bid for some exciting silent auction prizes, where proceeds will be benefiting the SOS Foundation and Food Pantry right here on Stock Island. Please bring a non-perishable food item to the SOS Foundation tent for their food drive. You won’t want to miss out!
Where: Bernstein Park- 6751 5th Street, Stock Island, FL 33040
When: Saturday June 14, 2025- 4pm-8pm
STOCK ISLAND MURAL ART TOUR
Set out on your own artistic scavenger hunt with the Stock Island Mural Art Tour, a captivating exploration of street art and creativity. This self-guided tour allows you to immerse yourself in the rich tapestry of murals that adorn the walls of Stock Island. Find one, find them all! Don’t forget to take a photo, post it and tag us! Remember to include #ilovestockisland
Where: Use the interactive map on the I Love Stock Island website to point you in the right direction so can find all these secret spots!
When: All weekend long!
Sunday, June 15, 2025
STOCK ISLAND HISTORY TOUR
Tour Stock Island in the comfort of Up The Keys’ air-conditioned tour van. In the one-hour tour, passengers learn about Stock Island’s rich history and colorful characters that have allowed for the preservation of the old Florida Keys lifestyle so that it is still present today. Limited space available. Advanced reservations required. Visit the event website to reserve your spot.
Where: The Perry Hotel & Marina, 7001 Shrimp Rd. Stock Island, FL 33040.
When: Sunday June 15, 2025- 10AM, 11AM, 1PM
STOCK ISLAND MURAL ART TOUR
Embark on a vibrant artistic journey with the Stock Island Mural Art Tour, a captivating exploration of street art and creativity. This self-guided tour allows you to immerse yourself in the rich tapestry of murals that adorn the walls of Stock Island. Find one, find them all! Don’t forget to take a photo and include #ilovestockisland
Where: Guide yourself with our interactive map on the I Love Stock Island website.
When: All weekend long!
THE PERRY MARINA & BAD BOY TAQUERIA & TEQUILA’S FESTIVAL CLOSEOUT BASH & POOL PARTY
Join us for an unforgettable finale to the “I Love Stock Island Festival” the Perry Marina & Bad Boy Taqueria and Tequila’s Festival Closeout Bash!
Bring your friends and family and let’s close out the I Love Stock Island Festival in Style with great food, drinks, music and community spirit! Don’t forget your swimming gear to enjoy a plunge in the Perry Marina’s pool next to Bad Boy’s restaurant. Enter the raffle for a chance to win some great prizes and proceeds from the raffle will benefit the SOS Foundation Food Pantry right here on Stock Island!
When: Sunday June 15, 2025- 2pm-6pm
Where: The Perry Marina & Bad Boy Taqueria & Tequila- 7011 Shrimp Road, Stock Island, FL 33040