Upcoming Events in Englewood FL 2026-2027
(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!
ANNUAL OR ONE TIME EVENTS IN ENGLEWOOD, FL
- OCTOBER 31, 2026 - HALLOWEEN SAFE WALK
Get your spooky on and cruise down Dearborn St for some Halloween fun.
Its the 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.
- NOVEMBER 12, 2026 - ENGLEWOOD NIGHT MARKET AND MUSIC
Kick off your weekend early with GBack’s Englewood Night Market and Music at the historic Pioneer Plaza! This vibrant evening event brings together over 40 local vendors, delicious food trucks, live music, and a welcoming community atmosphere. Enjoy shopping, dining, and entertainment under the lights in beautiful downtown Englewood — the perfect way to celebrate community and start the weekend right.
- NOVEMBER 14, 2026 - RED WHITE AND BREW
Join us for the 2nd Annual
Red, White & Brew
TOAST2TROOPS
at Pioneer Plaza in
Englewood, FL, for a day of free live music, food trucks, Craft beer tasting, and support for veterans, first responders,
and Gold Star Families
- NOVEMBER 22, 2026 - WIZARD OF OZ FAMILY FESTIVAL
On November 22, the Wizard of Oz-themed “There’s No Place Like Home” festival honors servicemen, veterans and their families. Musicians can take the open mic to share their name and branch or dedicate a song to someone who’s served. Along with the Kids Korner, the Colony is hosting a Korn Hole Tournament matching veterans with ROTC students, and veterans will get to pick a kiddo to compete with them
- DECEMBER 06, 2026 - HOLIDAY SHOWCASE
The Holiday Showcase wraps up the season on December 6. Alongside art and kids’ activities, musicians are welcome to play in an open mic session, with plenty of seasonal music. The headliners for the benefit show are still in the works.
- DECEMBER 10, 2026 -ENGLEWOOD NIGHT MARKET AND MUSIC
Kick off your weekend early with GBack’s Englewood Night Market and Music at the historic Pioneer Plaza! This vibrant evening event brings together over 40 local vendors, delicious food trucks, live music, and a welcoming community atmosphere. Enjoy shopping, dining, and entertainment under the lights in beautiful downtown Englewood — the perfect way to celebrate community and start the weekend right.
- 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 08-17, 2027 - Mr. Swindle's Traveling Peculiarium
Ninety minutes of world-class acrobatics, deliciously twisted comedy, and delightful mischief beneath our Boutique Big Top. So come in, leave your troubles outside, and remember: happiness can, in fact, be purchased.
- JANUARY 23, 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!
- JANUARY 23, 2027 -ENGLEWOOD CHILI COOKOFF
- JANUARY 28, 2027 -ENGLEWOOD NIGHT MARKET AND MUSIC
Kick off your weekend early with GBack’s Englewood Night Market and Music at the historic Pioneer Plaza! This vibrant evening event brings together over 40 local vendors, delicious food trucks, live music, and a welcoming community atmosphere. Enjoy shopping, dining, and entertainment under the lights in beautiful downtown Englewood — the perfect way to celebrate community and start the weekend right.
- FEBRUARY 13, 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.
- FEBRUARY 11, 2027 -ENGLEWOOD NIGHT MARKET AND MUSIC
Kick off your weekend early with GBack’s Englewood Night Market and Music at the historic Pioneer Plaza! This vibrant evening event brings together over 40 local vendors, delicious food trucks, live music, and a welcoming community atmosphere. Enjoy shopping, dining, and entertainment under the lights in beautiful downtown Englewood — the perfect way to celebrate community and start the weekend right.
- FEBRUARY 25, 2027 -ENGLEWOOD NIGHT MARKET AND MUSIC
Kick off your weekend early with GBack’s Englewood Night Market and Music at the historic Pioneer Plaza! This vibrant evening event brings together over 40 local vendors, delicious food trucks, live music, and a welcoming community atmosphere. Enjoy shopping, dining, and entertainment under the lights in beautiful downtown Englewood — the perfect way to celebrate community and start the weekend right.
- FEBRUARY 26-28, 2027 - SEAFOOD AND MUSIC FESTIVAL
Englewood Seafood & Music Festival will be located at the Englewood Elks Lodge at 401 North Indiana Avenue. The festival runs Friday from 4pm-10pm, Saturday from 11am-10pm, Sunday from 11am-6pm.
- FEBRUARY 28, 2027 - BEATLES THEMED FAMLIY FESTIVAL
Join the Englewood Art Colony for a Beatles-Themed Family Festival & Art Show! Celebrate the music and spirit of The Beatles with live entertainment, local artists, unique arts and crafts, food vendors, and family-friendly activities. Enjoy a groovy day filled with peace, love, music, art, and community fun in Englewood, Florida!
- MARCH 13, 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 20, 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.
- MARCH 11, 2027 -ENGLEWOOD NIGHT MARKET AND MUSIC
Kick off your weekend early with GBack’s Englewood Night Market and Music at the historic Pioneer Plaza! This vibrant evening event brings together over 40 local vendors, delicious food trucks, live music, and a welcoming community atmosphere. Enjoy shopping, dining, and entertainment under the lights in beautiful downtown Englewood — the perfect way to celebrate community and start the weekend right.
- MARCH 14, 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
- MARCH 25, 2027 -ENGLEWOOD NIGHT MARKET AND MUSIC
Kick off your weekend early with GBack’s Englewood Night Market and Music at the historic Pioneer Plaza! This vibrant evening event brings together over 40 local vendors, delicious food trucks, live music, and a welcoming community atmosphere. Enjoy shopping, dining, and entertainment under the lights in beautiful downtown Englewood — the perfect way to celebrate community and start the weekend right.
- APRIL 03, 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 08, 2027 -ENGLEWOOD NIGHT MARKET AND MUSIC
Kick off your weekend early with GBack’s Englewood Night Market and Music at the historic Pioneer Plaza! This vibrant evening event brings together over 40 local vendors, delicious food trucks, live music, and a welcoming community atmosphere. Enjoy shopping, dining, and entertainment under the lights in beautiful downtown Englewood — the perfect way to celebrate community and start the weekend right.
- APRIL 22, 2027 -ENGLEWOOD NIGHT MARKET AND MUSIC
Kick off your weekend early with GBack’s Englewood Night Market and Music at the historic Pioneer Plaza! This vibrant evening event brings together over 40 local vendors, delicious food trucks, live music, and a welcoming community atmosphere. Enjoy shopping, dining, and entertainment under the lights in beautiful downtown Englewood — the perfect way to celebrate community and start the weekend right.
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.
