Upcoming Events in Englewood FL 2026
(Festivals, Weekly Events & Things To Do)
Looking for the best events in Englewood, Florida? From annual festivals on Dearborn Street to weekly car shows, live music, and community gatherings, there’s always something happening around town. Whether you’re planning ahead or just looking for something to do this weekend, this page highlights the most popular events in Englewood FL, including local favorites and recurring events that bring the community together.
Englewood’s event scene is centered around Olde Englewood Village, the beaches, and nearby parks, giving everything a relaxed, coastal feel you won’t find in bigger cities. Check back often as new events are added and seasonal festivals return throughout the year.
The annual events are listed first and then we have a section for weekly and monthly events.
Englewood has a lot going on and you don't want to miss out.
Music Festivals, Food, Boat Races, Car Shows and More!
LIST OF ANNUAL EVENTS IN OR NEAR ENGLEWOOD, FL 2026
Pioneer Days
September 5-7th 2026
Pirate Poker Run
September 12, 2026
Englewood Beach Waterfest
October 08-11, 2026
Halloween Safe Walk on Dearborn.
October 31, 2026
Christmas on Dearborn
December 2026
BeerFest
January 2027
Cracker Fair
February 2027
Englewood Seafood & Music Festival
February 2027
Fly-in and Classic Cars
March 2027
Small Town Boots & Brew Country Music Festival
March 2027
Fine Art Festival
March 2027
Burgerfest in Paradise
April 2027
Venice Sharks Tooth Festival
April 2027
Woodstock Benefit Concert
April 2027
Englewood Art and Craft Show
April 2027
Boca H2O Music Festival
May 2027
Fireworks Show
July 04, 2027
ANNUAL OR ONE TIME EVENTS IN ENGLEWOOD, FL
WEEKLY & MONTHLY EVENTS
IN ENGLEWOOD, FL
ENGLEWOOD CAR SHOW - EVERY FIRST SATURDAY OF EVERY MONTH
The first Saturday of every month, Englewood has a car show, "Crusin' on Dearborn."
They usually have hundreds of cars, from old classics to new age power cars and everything in-between. Thousands of people flock this event and take in the beauty of the cars and trucks while listening to music played throughout the street.
ENGLEWOOD FARMERS MARKET EVERY THURSDAY FROM OCTOBER TO MAY
Englewood's Farmers Market is open every Thursday, from 9 AM to 1 PM. It is closed when the Thursday lands on a holiday.
It is located on Dearborn street at the Pioneer Plaza. Dogs are permitted if they are on a leash.
They have local organic produce, local fish, salsa, honey, syrups, baked good, plants, herbs and much more.
Englewood Beach Drum Circle
Every Sunday before sunset at Englewood Beach.
Englewood Beach is home to a vibrant drum circle that brings together locals and alike for a night of rhythm and community. Every week, participants gather on the sandy shore, creating a lively atmosphere filled with the sounds of drums, laughter, and camaraderie As the sun sets, the energy builds, fostering a sense of connection and joy among all who join in. Whether you're an experienced drummer or simply there to enjoy the music, the drum at Englewood Beach offers a unique and memorable experience.
Englewood Florida Events | Things to Do in Englewood FL
Looking for the best events in Englewood, Florida? This charming Gulf Coast town offers a wide variety of activities throughout the year including festivals, farmers markets, live music, community celebrations, art shows, and family-friendly events.
Whether you’re visiting Englewood Beach, Manasota Key, or Dearborn Street, there are always exciting things to do in Englewood FL. From seasonal festivals and outdoor markets to concerts and charity events, Englewood has something for visitors of all ages.
Browse upcoming Englewood Florida events and discover what’s happening during your visit.
Weekly Events in Englewood Florida
Englewood Farmers Market (Dearborn Street)
One of the most popular weekly Englewood events, the Englewood Farmers Market takes place every Thursday from October through May at Pioneer Plaza in Olde Englewood Village.
Visitors can shop from dozens of local vendors offering:
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Fresh Florida produce
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Gulf seafood
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Homemade baked goods
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Local honey and sauces
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Handmade crafts
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Plants and flowers
The Englewood Farmers Market is a great place to support local businesses while enjoying the lively atmosphere of Dearborn Street.
Live Music in Englewood Florida
Englewood has a lively music scene with live bands performing throughout the week at local restaurants, beach bars, and entertainment venues.
Popular places to hear live music in Englewood include venues near:
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Dearborn Street
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Englewood Beach
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Manasota Key
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Lemon Bay
Visitors can enjoy everything from rock and blues to country and tropical beach music while relaxing along the Gulf Coast.
Check Back Here to Stay Updated on Events in Englewood, Florida
These nearby destinations offer additional festivals, shopping, restaurants, and entertainment.
Check Back for Upcoming Englewood Events
Our calendar is regularly updated with new Englewood Florida events, festivals, markets, and community activities. Whether you’re planning a vacation or looking for something fun to do this weekend, Englewood offers plenty of exciting experiences along Florida’s beautiful Gulf Coast.
Bookmark this page and check back often to see the latest things to do in Englewood FL.