Top 8: Best FESTIVALS and EVENTS – Overseas Highway & Florida Keys

Top 8: Best FESTIVALS and EVENTS – Overseas Highway & Florida Keys

Embarking on a journey along the Overseas Highway winding through the enchanting Florida Keys is an adventure in itself. But what truly sets this iconic route apart are the vibrant festivals and events that punctuate its path, offering travelers an unparalleled cultural immersion and a taste of the unique island life.

From Key Largo to Key West, each mile of this scenic highway unveils a tapestry of celebrations, blending local flavors, music, art, and traditions. Whether you’re a music aficionado, a seafood lover, or a history buff, there’s something along this route to captivate every traveler’s heart.

In this blog post, I am thrilled to present the top eight festivals and events that showcase the rich tapestry of life along the Overseas Highway and throughout the Florida Keys. So buckle up, get ready to explore, and prepare to be swept away by the magic of these unforgettable experiences.

1. Seven Mile Bridge Run

Seven Mile Bridge Run - best festivals and events Overseas Highway

For fitness enthusiasts and adventure seekers alike, the Seven Mile Bridge Run is a must-attend event. Held each April, this iconic footrace spans the length of the historic Seven Mile Bridge, offering participants breathtaking views of the turquoise waters below. Whether you’re a seasoned runner or a casual jogger, crossing this engineering marvel on foot is an experience like no other.

The race begins on the north side of the bridge, near Marathon, and takes runners across the entire length of the bridge, offering stunning views of the surrounding seascape along the way. As participants pound the pavement, the cool ocean breeze and the rhythmic sound of waves crashing against the bridge’s supports create a truly memorable running experience.

But the Seven Mile Bridge Run is more than just a raceβ€”it’s a celebration of community and camaraderie. Spectators line the route, cheering on the runners and adding to the festive atmosphere. And for those not participating in the race, there are plenty of opportunities to join in the fun, with live music, food vendors, and other entertainment creating a lively festival atmosphere. The Seven Mile Bridge Run not only showcases the breathtaking beauty of the Overseas Highway but also highlights the vibrant spirit of the Florida Keys festival, making it a must-see event for runners and travelers alike.

2. Key Largo Original Music Festival

Key Largo Original Music Festival - get ready for your Florida Keys adventure with list of best festivals and events

Music lovers won’t want to miss the Key Largo Original Music Festival, a week-long celebration of live music and local talent. Held in various venues across Key Largo, this festival showcases a diverse lineup of musicians spanning genres from blues and rock to country and folk. With performances ranging from intimate acoustic sets to high-energy concerts, there’s something for everyone to enjoy.

The Key Largo Original Music Festival is a fantastic celebration of music set against the stunning backdrop of the Overseas Highway and the captivating Florida Keys. This vibrant festival not only showcases original music from talented artists but also offers attendees the opportunity to immerse themselves in the unique atmosphere of the Keys.

As you traverse the Overseas Highway, renowned for its breathtaking views of the azure waters and picturesque landscapes, you’ll find yourself drawn into the rhythm of the festival. From intimate performances in cozy waterfront venues to lively concerts under the stars, the Key Largo Original Music Festival offers an unforgettable experience for music lovers from around the world.

3. Underwater Music Festival

Underwater Music Festival - great festivals and events Florida Keys, Overseas Highway.

The Underwater Music Festival is a unique event held annually in the Florida Keys, where music enthusiasts and environmentalists come together for an extraordinary underwater concert experience. Established in 1985, this festival takes place in the waters of Looe Key Reef, located about six miles south of Big Pine Key. Participants, adorned in creative underwater costumes and equipped with specially designed underwater instruments, dive beneath the surface to enjoy live music performances. The festival not only celebrates music but also promotes reef preservation and marine conservation awareness, emphasizing the importance of protecting our underwater ecosystems.

As you travel along the Overseas Highway in the Florida Keys, keep an eye out for the vibrant banners and signs welcoming you to the Underwater Music Festival. It’s a sight that perfectly encapsulates the eclectic and adventurous spirit of the Keys, inviting you to dive into a world where music and nature harmoniously coexist beneath the waves.

4. Key West Food & Wine Festival

Key West Food & Wine Festival - top 8 festivals and events in summer along scenic Overseas Highway

The Key West Food & Wine Festival is a culinary extravaganza held annually in the charming island city of Key West, Florida. Established to celebrate the diverse flavors and vibrant culinary scene of the Florida Keys, this festival brings together renowned chefs, talented mixologists, and wine experts for a week-long celebration of food and drink.

Throughout the festival, visitors can indulge in a wide array of culinary delights, from fresh seafood dishes to creative cocktails crafted with local ingredients. Events include wine tastings, cooking demonstrations, interactive workshops, and extravagant tasting events held at various venues across Key West.

As you travel along the Overseas Highway through the Florida Keys, keep an eye out for advertisements and banners promoting the Key West Food & Wine Festival. It’s a must-see event for food enthusiasts and wine connoisseurs alike, offering a taste of the unique flavors and culinary traditions that make the Keys a culinary destination worth exploring.

5. Fantasy Fest

Fantasy Fest - get ready for your next adventure with my list of best road attractions, festivals, and events Overseas Highway and Key West.

When traveling along the Overseas Highway and through the Florida Keys, keep an eye out for billboards and signs advertising Fantasy Fest. It’s a spectacle worth witnessing, offering a unique blend of creativity, eccentricity, and unbridled fun that captures the essence of Key West’s spirited culture and community. Whether you’re a participant or a spectator, Fantasy Fest promises an unforgettable experience unlike any other.

Fantasy Fest is a one-of-a-kind celebration held annually in Key West, Florida, known for its vibrant costumes, lively parades, and uninhibited revelry. This 10-day festival, which typically takes place in late October, transforms the island into a colorful spectacle of creativity and fantasy, drawing thousands of visitors from all over the world.

The festival originated in 1979 as a way to boost tourism during the shoulder season and has since evolved into one of the largest and most famous costume festivals in the United States. Each year, Fantasy Fest adopts a different theme, inspiring participants to unleash their imagination and dress up in elaborate costumes ranging from the whimsical to the outrageous.

Throughout the festival, Key West comes alive with a diverse array of events and activities, including themed costume parties, street fairs, art shows, live music performances, and body painting competitions.

6. Key Lime Festival

Key Lime Festival - very famous festival Florida Keys.

The Key Lime Festival is a delightful celebration of one of Florida’s most iconic flavors, the tangy and refreshing key lime. Held annually in the Florida Keys, this festival pays homage to the beloved key lime through a variety of culinary events, tastings, and competitions.

During the Key Lime Festival, visitors can indulge in a plethora of key lime-inspired dishes and treats, including pies, cocktails, ice creams, and savory dishes infused with the bright and zesty flavor of this tropical fruit. From traditional key lime pie baking contests to creative cocktail competitions, the festival showcases the versatility of key lime and the creativity of local chefs and mixologists.

One of the highlights of the Key Lime Festival is the Key Lime Pie Hop, where participants can embark on a delicious journey to sample different variations of this classic dessert at various restaurants and bakeries throughout the Florida Keys & Overseas Highway. Additionally, the festival features live music performances, cooking demonstrations, and family-friendly activities, making it an enjoyable experience for visitors of all ages.

7. Goombay Festival

Goombay Festival - summer party. Overseas Highway and Florida Keys events.

Immerse yourself in the vibrant culture of the Bahamas during the Goombay Festival in Key West. Held in October, this lively street festival celebrates Bahamian heritage with Caribbean music, dance performances, and delicious island cuisine. Get ready to dance to the rhythm of steel drums and savor the flavors of the Caribbean.

During the Goombay Festival, the streets of Key West’s historic Bahama Village come alive with music, dance, food, and art, creating an atmosphere of jubilation and camaraderie. The festival features live performances of traditional Bahamian music, including Junkanoo bands, reggae, calypso, and soca, filling the air with infectious rhythms and melodies that beckon visitors to dance along.

One of the highlights of the Goombay Festival is the vibrant street parade, where costumed dancers, stilt walkers, and marching bands parade through the streets of Bahama Village, delighting spectators of all ages. When traveling along the Overseas Highway and through the Florida Keys, keep an eye out for signs and advertisements promoting the Goombay Festival.

8. Key West Literary Seminar

Key West Literary Seminar - most famous festivals and events summer in the Florida Keys.

The Key West Literary Seminar is an annual gathering of writers, readers, and literary enthusiasts held in Key West, Florida. Established in 1983, this renowned literary event brings together some of the most esteemed authors, poets, journalists, and scholars from around the world for a series of lectures, panels, workshops, and readings.

Each year, the Key West Literary Seminar explores a different theme or topic of literary significance, inviting participants to engage in thought-provoking discussions and exchanges about literature, culture, and society. Past seminars have focused on themes such as “Writers on Writers,” “New Voices, Old World,” and “Writers of the Caribbean.” Undoubtedly, a must-see festival along your journey on the Overseas Highway through the Florida Keys.

If you’re in Key West, be sure to check out my blog post about clubs and bars here: The Nightlife of Key West: 8 TOP Bars, Clubs, and Entertainment Venues

πŸ‘ Find out more:

Overseas Highway Florida Keys Travel Guide - 101 best stops by Mark Watson

Explore the finest attractions along the Overseas Highway and Florida Keys with my travel guide, ‘Florida Keys Overseas Highway Travel Guide – 101 Best Stops,’ now available on Amazon. This comprehensive guide is your ultimate companion for those seeking adventure and wonder along THE OVERSEAS HIGHWAY & FLORIDA KEYS! Discover 101 amazing places with convenient ‘Scan QR and go’ functionality for easy navigation.


Pacific Coast - Mark Watson

Mark Watson is a California-based member of a Los Angeles motorcycle club and an avid traveler. He has completed seven full journeys along the iconic Pacific Coast Highway on his Harley-Davidson and is passionate about promoting this historic drive to others. Mark has also explored the Alaska Highway and Route 66, and has authored four bestselling travel guides on Amazon: “Route 66 Travel Guide – 202 Amazing Places,” “Alaska Highway Travel Guide – 202 Best Stops,”, “Pacific Coast Highway Travel Guide – 202 Best Stops”, and “Florida Keys Overseas Highway Travel Guide – 101 Best Stops.”

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