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
Englewood Art and Craft Show
April 18-19 2026
Boca H2O Music Festival
May 23, 2026
Fireworks Show
July 04, 2026
Pioneer Days
September 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
ANNUAL OR ONE TIME EVENTS IN ENGLEWOOD, FL
- MAY 23, 2026 - BOCA H2O FEST
The most anticipated event of the year in Southwest Florida! The Boca H2O music Festival is the largest Music Festival on the water in the South East united States! The stage is literally floating, and you must get there by boat, tube, kayaks or anything else that will get you there!
- JULY 4TH 2026 - FIREWORKS SHOW
The fireworks will be shot from the end of Dearborn St.
Every year this show does a spectacular job!!
Like other fireworks shows, Englewood's will start after dusk.
SEPTEMBER 2026
PIONEER DAYS
A Labor Day Weekend Tradition on Dearborn Street
Pioneer Days in Englewood, Florida is one of those events locals plan their weekend around. It’s been part of the community for years, built around celebrating Englewood’s history, but it’s just as much about getting everyone together downtown.
SEPT 12, 2026 - PIRATE POKER RUN
Get into your pirate gear, and sail your ship around Lemon Bay, pillaging select restaurants and bars for their poker chip so you can have a seat at the pirate table.
Everyone dresses up as a pirate, including your favorite servers and bar tenders. You can win prizes for having the best hand in poker or by winning a raffle
OCTOBER 08-11, 2026 - WATERFEST
Speed, Power and Excitement comes to Englewood, Florida! Watch thrilling offshore powerboat racing from Englewood Beach as boats gather points for the world championship races! This is the World Championships for OPA Racing (Offshore Powerboat Association) with 75+ boats running at speeds up to and over 150 miles per hour
- OCTOBER 31, 2026 - HALLOWEEN SAFE WALK
Get your spooky on and cruise down Dearborn St for some Halloween fun.
Its the 27th Annual Halloween Safe Walk, where you can take the kids to get their tricks and treats, pass out candy and listen to some music.
The walk usually takes place from about 5pm to dusk and will have contests for the best Halloween costumes. The turnout is always pretty good and its fun for everyone.
- DECEMBER, 2026 -
CHRISTMAS ON DEARBORN ST.
2026 Christmas Festival at Old Englewood Village on Dearborn St (Pioneer Plaza).
This family-friendly event features Mr. and Mrs. Claus, food vendors, music, a bicycle raffle, and a decorated golf cart parade.
- JANUARY 2027 - BEER FEST
Get ready to drink up and have a blast at Beerfest 2026 - the ultimate beer lover's paradise!
Beerfest 2026 is back and better than ever! Join us for a day filled with amazing brews, delicious food, and live music featuring Pure Country at Pioneer Plaza/335 W Dearborn St. Get ready to sample a wide variety of craft beers from local breweries and enjoy the vibrant atmosphere with fellow beer enthusiasts. Whether you're a seasoned beer connoisseur or just looking to have a good time, Beerfest is the place to be. Don't miss out on this epic event!
- FEBRUARY 2027 - CRACKER FAIR
The Cracker Fair in Englewood is an annual "Celebration of Old Florida" held at Pioneer Plaza on Dearborn Street. Organized by the Lemon Bay Historical Society.
MARCH 2027 - SEAFOOD AND MUSIC FESTIVAL
Englewood Seafood & Music Festival has everything you need if "The Plan" is to spend the weekend unwinding, having fun, eating delicious cuisine, and enjoying live music. The event will take place this year at Pioneer Park, which is off West Dearborn Street.
Choose from a wide selection of fish, meat, and vegetarian dishes that are all freshly prepared on location by neighborhood restaurants and food suppliers.
Listen to some of Florida's greatest musical acts while indulging in delicious food from genres like R&B, blues, jazz, rock, and fresh Caribbean sounds.
- MARCH 2027 - FLY-IN AND CLASSIC CARS
The Buchan Airport Fly-In & Classic Car Show in Englewood, FL, is an annual community event featuring vintage aircraft displays, helicopter rides, and over 170 classic cars, held at Buchan Airport (X36)
MARCH 2027 SMALL TOWN BOOTS AND BREW
A Night of Country Music, Dancing & Ice-Cold Drinks – All for a Great Cause!
Calling all country music lovers, line dancers, and festival-goers! The Small Town Boots & Brews Country Music Festival is back for its 2nd annual event in beautiful Englewood, Florida. This all-day festival brings together top country music artists, incredible drinks, delicious food, and non-stop entertainment—all while supporting the Englewood Sunrise Rotary’s mission to give back to the community.
-MARCH 2027 -
FINE ART FESTIVAL
You are cordially invited to join us on Dearborn Street in Olde Englewood Village for our Spring Fine Arts Festival!
Newly revived and sparkling with old-world charm, this once sleepy town transforms into a pedestrian-only artist's village.
- APRIL 2027 WOODSTOCK BENEFIT CONCERT FOR ST. DAVID’S JUBILEE CENTER
Woodstock festival music will begin at 2pm with rock portion beginning at 5pm.
Still planning and will have morning and early afternoon activities prior to the concert beginning.
* entrance fee = food (not expired please) or cash donation at the gates.
Raffles and live auction during music breaks.
* bring your chairs and coolers allowed. Food and beverages will be available. Including beer service
- APRIL 2027, BURGERFEST -
Who has the best burger in town?
It turns into a bit of friendly competition, both for the vendors and for the people walking around debating which one actually deserves the top spot.
- APRIL, 2027 - VENICE SHARKS TOOTH FESTIVAL
Yes, not in Englewood, but our sister city has something fun going on in April. Welcome to the Venice, FL Sharks Tooth Festival! Join us for an exciting weekend filled with live music, delicious food, and fun activities for the whole family.
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.
