The Farmers Markets On Dearborn Street

 Every Thursday Morning Oct - May on Dearborn Street is the place to be from 9:00 AM to 1:00 PM, .

 This local staple brings a vibrant energy right to the heart of Old Englewood Village. 

Whether you are looking for the freshest local produce, handmade artisan goods, or just a beautiful morning stroll through town, the street comes alive with a welcoming community atmosphere that you will not want to miss.

What makes this event truly unique is that you get 4 incredible, independent markets all on one single street. You can easily wander between:

• The Market on Dearborn
• Olde Englewood Village Farmers Market
• Dearborn Street Market
• Sea Star Cove Farmers Market

Each stop offers its own distinct selection of local vendors, giving you the perfect opportunity to support small businesses.

 Bring your appetite, grab your reusable shopping bags, and come see why Thursday mornings are a favorite local tradition. 

Mark your calendar for this Thursday between 9:00 AM and 1:00 PM and enjoy everything these 4 independent markets have to offer. 

First Thursday In October - 2026

Till:  Last Thursday In May 2027

Every Thursday 9am to 1pm

  The Thursday Market On Dearborn 

 232 W Dearborn St., Englewood, Fl. 

First Thursday In October - 2026

Till:  Last Thursday In May 2027

Every Thursday 

9am to 1pm

Come out for fresh produce, handmade goodies, local eats, and live vibes.

Englewood Night Market & Music:

 A vibrant evening gathering featuring more than 40 local craft and artisanal vendors, food trucks, and live local music. It runs from 

5:00 PM to 9:00 PM on the following dates:

• October 8, 2026 (Featuring live music from The Outsiderz)
• November 12, 2026
• December 10, 2026

Cruizin’ on Dearborn

 Sponsored by Looney Electric 

1st Saturday of The Month

The Kooky Catman will be their crusin' in one of The Pop Culture Antique Museum crazy PR vehicles, along with hundreds of cars and thousands of car lovers converge on Dearborn Street for this car show.

Music to cruise by Tom's Traveling Tunes

  ⭐ TOAST 2 TROOPS: RED, WHITE & BREW FEST ⭐

• WHO: Proudly Hosted by Operation Healing Heroes Foundation
• WHAT: Red, White & Brew Fest 🍻🎶
• WHEN: Saturday, November 14, 2026
• TIME: 12:00 PM – 6:00 PM
• WHERE: Pioneer Plaza (325 W Dearborn St., Englewood, FL 34223)

🎉 ALL THE FUN STUFF HAPPENING 

• Jessie G – Headlining Nashville Recording Artist
• Dave Bray USA – Live musical performer
• Hit Machine – Live musical performer
• Paul Sr. of Orange County Choppers – Special appearance

!Get ready for an action-packed afternoon of non-stop excitement! We are bringing the community together with an incredible lineup of live musical performances rocking the stage all day long. 

Come hungry and thirsty—we’ve lined up a massive variety of local food trucks serving up delicious eats alongside a refreshing selection of ice-cold craft beers and drinks.

 Families will love the vibrant festival atmosphere, complete with unique artisan and craft merchandise booths to browse, interactive business exhibits, and plenty of fun activities for all ages. It's the ultimate block party with a patriotic heart!

🦅

LET'S MAKE A BIG IMPACT TOGETHER!
Support local. Support our veterans. Support the mission. 

 WHO: Family Festival Celebrating Veterans & Servicemen
WHAT: "There's No Place Like Home" Wizard of Oz Festival
WHEN: Sunday, November 22, 2026 | 10:00 AM to 3:00 PM (Live music starting at 2:00 PM)
WHERE: Pioneer Plaza (In Front of the Englewood Mural) | 10:00 AM to 3:00 PM (Concert at 2:00 PM)

Follow the yellow brick road to Pioneer Plaza for an autumn community 

celebration honoring our local veterans and active servicemen starting at 10:00 AM. 

The festival kicks off with a special community open mic invitation where our veterans are welcome to take the stage and share their voices during the day.

The festival atmosphere transitions at 2:00 PM into an exceptional evening concert program headlining "The Old Glory Band" performing classic rock sets live under the plaza lights. 

Grab a spot on the grass, connect with friends and neighbors, and settle in for a memorable night of music, tribute, and neighborhood spirit until the event wraps up at 3:00 PM.

Explore a unique festival layout that brings the fantasy of Oz straight to the heart of the village. 

From silhouette displays of Dorothy and the crew to flying monkeys hovering along the prominent corridor backdrop, this family-friendly setting provides the perfect backdrop for autumn memories while showing active support for those who served.

WHAT: The 2026 Holiday Showcase 

WHO: Presented by The Artist Colony in Englewood
WHEN: Sunday, December 6, 2026 | 10:00 AM to 3:00 PM (Live music starting at 2:00 PM)

WHERE: Pioneer Plaza on Historic Dearborn Street

Kick off the festive season in the heart of the village with an all-day celebration of music and neighborhood spirit starting at 10:00 AM. Local musicians will take the stage at Pioneer Plaza to perform your favorite classic carols, timeless holiday melodies, and standard seasonal choices that everyone knows and loves.

It is the perfect opportunity to bring your neighbors together, relax under the Florida winter sky, and immerse yourself in the unique festive energy of Historic Dearborn Street. 

Grab your favorite spot, settle in with the community, and enjoy the outdoor market and festive activities running until 3:00 PM.

This community gathering shines a spotlight on our exceptional regional talent while providing a warm, welcoming space for friends and families to connect. 

With the main live music performances kicking off at 2:00 PM and leading straight into the evening concert program, you will find plenty of holiday cheer to share with the neighborhood.

 WHAT: The 2026 Christmas Festival & Parade
WHO: Sponsored by the Old Englewood Village Association
WHERE: Historic Dearborn Street & Pioneer Plaza
WHEN: Date and Time To Be Announced

Bring the neighborhood together and dive into the holiday spirit as Historic Dearborn Street transforms into a massive winter celebration. 

The annual parade procession will feature incredible regional talent and vibrant seasonal performances from local school groups, including full marching sets from the Lemon Bay High School Marching Band alongside heartwarming holiday numbers from the Englewood Elementary 4th and 5th-grade choirs.

The excitement continues right down the street with a unique fleet of decorated golf carts, a custom bicycle raffle, and a highly anticipated appearance by Mr. and Mrs. Claus.

 It is the perfect opportunity to line the sidewalks, wave to the marchers, and catch up with old friends under the evening sky.

As the parade wraps up, the celebration moves directly to Pioneer Plaza for an unforgettable evening under the stars. 

The plaza will be bustling with local food trucks, seasonal treats, and interactive community activities for everyone to enjoy.

 Settle in with your lawn chairs, enjoy the live holiday music filling the air, and let the unique charm of Old Englewood set the perfect tone for a wonderful festive season.

 Mr. Swindle's Traveling Peculiarium 

• Dates: January 8–17, 2027 
• Venue: Under The Big Top at Pioneer Plaza, 325 W Dearborn Street, Englewood, FL 34223 
• Runtime: 90 minutes plus a 15-minute intermission 
• Description: A theatrical variety production blending vintage circus arts, acrobatics, illusionists, vaudeville, and comedy under a traditional tented big top. 

Prepare to step into an extraordinary world of vintage intrigue, high-flying stunts, and eccentric characters at Mr. Swindle’s Traveling Peculiarium. 

This premier traveling circus brings a brilliant fusion of vaudeville charm, world-class acrobatics, and hilarious adult comedy straight to the neighborhood. From the moment you approach the iconic big top, the lively and immersive old-school carnival atmosphere invites guests to leave reality behind and indulge in a captivating, grown-up theatrical experience unlike any other. 

Under the grand tent, a spellbinding variety show unfolds, starring a bizarre yet incredibly talented troupe of global performers. 

Audiences will be treated to breathtaking displays of aerial artistry, gravity-defying balance acts, and fast-paced variety routines that keep the energy electric from start to finish. Woven seamlessly into these stunning feats are a series of mischievous comedic sketches and a delightfully eccentric narrative hosted by the mysterious Mr. Swindle himself, ensuring continuous entertainment for all who enter. 

Complementing the performance is the unique festival garden, a specialized outdoor oasis where attendees can gather before and after the main attraction.

 Guests can browse an array of quirky, vintage-style displays and interactive areas while enjoying a selection of delicious local snacks and refreshments. Whether you are a dedicated lover of modern variety theatre or simply looking for an unforgettable night out with neighbors and friends, this phenomenal traveling production offers a masterful blend of amusement, wonder, and community fun.

  WHAT: The Englewood Beer Fest
WHO: Sponsored by the Englewood Sunset Rotary Club
WHERE: Pioneer Plaza on Dearborn Street
WHEN: Date and Time To Be Announced 

 Get ready for the ultimate celebration of local flavor, cold brews, and community spirit as historic Dearborn Street transforms for the annual Englewood Beer Fest. 

This premier event brings together passionate craft beer lovers, incredible live music, and the best local food vendors right in the heart of Olde Englewood Village. 

It is the perfect opportunity to kick back, catch up with neighbors, and soak in the absolute best of Southwest Florida’s laid-back coastal vibe.

Step into the expanded beer garden where you can unlock an extensive lineup of exceptional local and regional craft breweries.

 Your tasting experience features a diverse selection of ice-cold samples, ranging from bold signature ales to distinct seasonal creations poured directly by the region's finest makers. 

As you sip your way down the historic corridor, the outdoor spaces stay completely energized with a full food truck lineup serving savory favorites alongside live musical acts keeping the festival vibes moving all day long.

Best of all, this spectacular community gathering combines a fantastic time out with a meaningful mission to support local charitable initiatives.

 Organized annually, the festival fun direct-connects neighbors, regional visitors, and small businesses to raise resources that pour right back into the local community. 

Make sure to clear your schedule, assemble your friends, and prepare for an unforgettable weekend celebration packed with high-energy entertainment and excellent flavor.

WHAT: The 23rd Annual Cracker Fair
WHO: Presented by The Lemon Bay Historical Society
WHERE: Pioneer Plaza on Dearborn Street, Englewood, Florida
WHEN: Saturday, February 13th from 10:00 AM to 4:00 PM (Free Admission)

Step back in time and immerse yourself in the rich heritage of the Sunshine State at the 23rd Annual Cracker Fair. 

Hosted by the Lemon Bay Historical Society, this highly anticipated community tradition transforms Pioneer Plaza into a lively festival grounds dedicated to celebrating Old Florida culture. 

Running from 10:00 AM to 4:00 PM on Saturday, February 13th, the event offers completely free admission for the whole family, making it the perfect weekend destination to connect with neighbors and experience the area's deep-rooted history.

The festival grounds will be bursting with classic entertainment, interactive heritage showcases, and lively local vibes. 

Attendees can pull up a chair to enjoy a full lineup of live, local music while exploring various historical demonstrations that bring pioneering traditions to life. 

The air will be filled with the enticing aromas of local food trucks, and a diverse marketplace of unique arts, crafts, and merchandise vendors will offer the perfect opportunity to find one-of-a-kind goods while supporting small regional businesses.

One of the day’s most exciting highlights is the famous Lemon Dessert Baking Contest alongside the traditional Florida whip cracking demonstrations. 

The thundering pop of the traditional cracker whips will bring the authentic spirit of Florida's cowboy history straight to the plaza, matching the fun energy of the baking competition. Gather your friends and family, mark your calendars for Saturday, February 13th, and head down to Dearborn Street to celebrate the timeless spirit of Old Florida..

 ENGLEWOOD SEAFOOD & MUSIC FESTIVAL

• WHAT: The 7th Annual Englewood Seafood & Music Festival
• WHO: Open to the general public with Free Admission (Fun for families, foodies, music lovers, and local shoppers)
• WHERE: Englewood Elks Lodge, 401 North Indiana Avenue, Englewood, FL 34223
• WHEN: February 26–28, 2027
  • Friday, February 26: 4:00 PM – 10:00 PM
  • Saturday, February 27: 11:00 AM – 10:00 PM
  • Sunday, February 28: 11:00 AM – 6:00 PM

Get ready for a spectacular weekend of flavor and sound at the 7th Annual Englewood Seafood & Music Festival, returning to the Englewood Elks Lodge at 401 North Indiana Avenue from February 26–28, 2027. 

This highly anticipated, three-day community celebration is completely free to attend, welcoming locals and visitors alike to gather, unwind, and experience the very best of Florida's Gulf Coast culture.

The heart of the festival lies in its incredible culinary and musical showcase, offering a feast for all the senses. 

Seafood lovers can dive into an array of fresh, sustainably sourced Florida Gulf Coast dishes, alongside plenty of classic meat and vegetarian options, delicious sides, desserts, and refreshing drinks. 

As you dine, the main stage will come alive with an incredible lineup of regional and top-tier musical acts, pumping out live rock, blues, R&B, jazz, and vibrant Caribbean tunes all weekend long.

Beyond the food and music, the festival features an expansive outdoor marketplace perfect for weekend browsing. 

Attendees can explore a diverse open-air shopping area packed with unique arts, handmade crafts, gourmet food items, and specialty products from local creators and vendors. 

Whether you are coming out to dance, grab a great meal, or shop local businesses, this premier Englewood event delivers the ultimate weekend destination. 

 BEATLES-THEMED FAMILY FESTIVAL & ART SHOW

• WHAT: The Beatles-Themed Family Festival & Spring Art Show
• WHO: Hosted by The Artist Colony (Fun for all ages, families, art lovers, and music fans)
• WHERE: Pioneer Plaza, Historic Dearborn Street, Englewood, FL (Right next to Sip Sip Hooray Garden Café and Mango Bistro)
• WHEN: Sunday, February 28, 2027
  • Main Family Festival & Art Show: 10:00 AM – 3:00 PM
  • Headline Tribute Concert Sets: 4:00 PM – 7:00 PM (Late afternoon slots)

Get ready to twist and shout down memory lane at the spectacular Beatles-Themed Family Festival, rocking Pioneer Plaza on Sunday, February 28, 2027. 

This vibrant community celebration seamlessly combines the stunning Spring Art Show with a sensational Beatles Tribute Benefit Concert. Designed as a high-signal, family-friendly gathering, the event invites music lovers and families to come together for a day of classic tunes and local culture, all while supporting a fantastic cause with a simple food or cash donation at the gates.

The daytime festivities kick off with an expansive open-air market organized by The Artist Colony

. Visitors can stroll through a curated showcase featuring the region's finest local vendors, craftsmen, and creators displaying exquisite paintings, hand-thrown pottery, intricate fused glass, and beautiful custom jewelry. 

As you explore the creative talent of the Gulf Coast, the air will be filled with the timeless sounds of the Fab Four, creating an electric, nostalgic atmosphere that bridges generations.

As the sun begins to set over Historic Dearborn Street, the energy rises with headline tribute sets and main-stage concert programming extending straight into the late afternoon.

 Whether you are dancing along to your favorite rock hits, browsing unique local goods, , this premier festival promises the ultimate weekend destination. It is a brilliant opportunity to celebrate community spirit, honor great music, and support music instruments for local students. .

  Event Name: Buchan Airport Fly-In & Classic Car Show

• Date & Time: Saturday, March 13, 2027, from 9:00 AM – 2:00 PM (Car show portion typically runs 10:00 AM – 1:00 PM, with trophies around 12:30 PM)
• Location: Buchan Airport, 1390 Old Englewood Road, Englewood, FL 34223
• Admission: Free for general spectators (donations encouraged to support local student scholarships); $10 registration/donation fee for show cars.
• Features: Dozens of airplanes and helicopters on display, a classic car show presented by the Florida West Coast Car Club, music by Tom's Traveling Tunes, and food/vendors available for purchase (including Libee's Sports Bar & Grill).

Get ready for an action-packed day where the skies meet the asphalt at the Buchan Airport Fly-In & Classic Car Show, taking off on Saturday, March 13, 2027. 

This unique community gathering transforms the airfield into a high-signal paradise for aviation enthusiasts and automotive fans alike. 

General admission is completely free for spectators, though gearheads looking to put their prized rides on display can enter the showcase for a minor ten dollar registration fee, with all collected funds going directly toward supporting local student 

scholarships.

The grounds will come alive with dozens of spectacular airplanes and helicopters parked right on the tarmac for close-up viewing, offering an incredible look at classic and modern aviation history. Right alongside the aircraft, the Florida West Coast Car Club will present a magnificent classic car show featuring pristine restoration models, muscle cars, and vintage rides competing for trophies. 

With the energetic sounds of Tom's Traveling Tunes pumping through the air and fantastic food options like Libee's Sports Bar & Grill cooking up fresh bites, this high-energy neighborhood event delivers an unforgettable local experience. .

   SALUTE TO WOODSTOCK BENEFIT FESTIVAL

• WHAT: The Annual "Salute to Woodstock" Benefit Festival & Open-Air Market. 
• WHO: Organized and presented by The Artist Colony in Englewood (Fun for 1960s music fans, classic rock lovers, families, and local art collectors).
• WHERE: Held live on the main stage layout at Pioneer Plaza, located at 325 W. Dearborn Street, Englewood, FL 34223. 
• WHEN: Sunday, March 14, 2027 (Daytime Art Show starts at 10:00 AM; Live Woodstock tribute music performances kick off on stage at 2:00 PM).

Dust off your favorite vintage threads, grab your lawn chairs, and get ready to relive the legendary days of peace and love at the "Salute to Woodstock" Benefit Festival. Spearheaded by The Artist Colony.

 This highly anticipated annual celebration channels the ultimate 1960s counterculture movement right onto the main pavement of Historic Dearborn Street. 

Admission is simple and community-focused: visitors are asked to bring a donation of cash or non-perishable food items at the gates, with all collected proceeds directly funding vital regional crisis centers like St. David's Jubilee Center to keep local food resources strong. 

The high-energy festivities break out early in the day, launching an expansive outdoor market where talented Gulf Coast craftsmen and artists showcase brilliant selections of original fine art and handmade goods. 

As the afternoon rolls in, the open-air venue transforms into a powerhouse tribute concert, featuring premier regional headline musicians delivering live covers of the iconic rock, blues, and folk bands that defined the 1969 counterculture movement. 

Complete with excellent food trucks, refreshing local beverage stations, and dynamic charity auctions during music breaks, this premier festival provides a phenomenal destination to celebrate historic music while delivering critical support to the local community. 

4th Annual Small Town Boots & Brews Country Music Festival

• Date & Time: Saturday, March 20, 2027, from 10:00 AM to 10:00 PM
• Location: Pioneer Plaza, 325 W. Dearborn St., Englewood, FL 34223
• Organizer: Lemon Bay Sunrise Rotary
• Entertainment: Non-stop live country music and Southern rock acts on the main stage, a dedicated line dancing floor, and full-service bars.
• Food & Drink: A wide selection of local food trucks alongside craft beers, wine, and mixed beverages.
• Admission: Small entry donation at the gate (suggested $3), with children ages 12 and under admitted for free.
• Purpose: All proceeds directly fund local charitable initiatives, including student scholarships and community programs. 

What started as a cozy community gathering has exploded into one of Englewood’s most anticipated block parties, expanding across both sides of West Dearborn Street to accommodate thousands of enthusiastic fans. 

The massive venue transformation turns the historic district into an open-air entertainment hub complete with massive sound stages, sprawling vendor markets, and high-energy party zones. Because the festival stretches late into the evening, it draws an incredibly diverse, high-energy crowd that packs the downtown strip from morning until the final encore. 

The festival has become a massive magnet for young adults, college students, and younger families from all over Southwest Florida who come out to celebrate the region's vibrant country culture. 

The combination of modern country-pop hits, social-media-friendly food trucks, and lively group line dancing creates a dynamic, festival-style atmosphere that appeals heavily to the younger demographic.

 Whether hitting the massive dance floor with friends or hanging out by the full-service bars under the stars, the younger crowd injects a distinct, buzzing energy into the heart of Pioneer Plaza

 ENGLEWOOD FINE ART FESTIVAL

• WHAT: The Annual Rotary Club of Englewood Fine Arts Festival.
• WHO: Organized by the Rotary Club of Englewood and the Englewood Youth Foundation, open to all residents, tourists, art collectors, and families.
• WHERE: Hosted entirely on pedestrian-only  Dearborn Street in Olde Englewood Village, Englewood, FL 34223.
• WHEN: Late March Weekend (Traditionally scheduling Saturday and Sunday) from 10:00 AM to 4:00 PM daily.

Step into an open-air wonderland of creativity at the annual Englewood Fine Arts Festival. 

For one spectacular weekend, historic West Dearborn Street sheds its regular routine and transforms into a sprawling pedestrian-only outdoor gallery.

 This long-running neighborhood tradition seamlessly blends the charm of downtown’s boutique shops and local restaurants with an upscale art exhibition, drawing thousands of enthusiastic visitors to the heart of Olde Englewood Village to celebrate community spirit and fine culture.

The festival serves as a premier showcase for master artisans, craftsmen, and creators traveling from across the state and country to display their talents.

 Visitors can take their time strolling between beautiful booth displays packed with striking 2D and 3D original works, including fine paintings, handcrafted pottery, intricate jewelry, photography, and custom sculptures. 

Beyond the visual displays, the weekend is packed with lively street entertainment, live music performances, and local food vendors cooking up delicious eats, making it a true feast for all the senses.

Best of all, this iconic weekend is highly purposeful, ensuring every dollar spent goes back into reinforcing the local community.

 Entry generally asks for a small optional donation at the gate to directly benefit The Englewood Youth Foundation, Inc. and various vital civic Rotary projects. 

Whether you are a serious collector hunting for your next masterpiece, a local looking to enjoy the seasonal sunshine, or a vendor connecting with an energetic crowd, this premier fine arts market delivers an unmissable downtown experience. 

 BURGERFEST IN PARADISE

• WHAT: BurgerFest (Burgerfest in Paradise) — The Ultimate Local Grill-Off Competition.
• WHO: Hosted by the Rotary Club of Englewood Sunset Impact, Inc. (Fun for backyard grill masters, foodies, families, and burger lovers).
• WHERE: Pioneer Plaza, 325 West Dearborn Street, Englewood, FL 34223.
• WHEN: Saturday, April 3, 2027, from 11:00 AM – 3:00 PM.
• COST: Free Admission to enter! Food and drink purchases are required separate, with creative burger tasting portions typically running around 5 dollars each. (Remember to bring your own lawn chair for seating!)

Fire up the charcoal and bring your appetite down to Pioneer Plaza for the high-signal flavor showdown of the season at BurgerFest in Paradise.

 Launching on Saturday, April 3, 2027, this premier outdoor culinary competition brings together the finest local grill teams and professional chefs to go head-to-head in a live, open-air charcoal battle. 

Admission to the venue is completely free, making it the perfect neighborhood destination to drop in, grab a spot on the pavement, soak up the sun, and watch local masters flip, stack, and sear their ways toward trophies and ultimate backyard bragging rights.

The heart of the festival is a massive interactive tasting experience where you get to be the judge. For roughly 5 dollars per tasting portion, attendees can sample a spectacular variety of custom, creative burger creations stacked with unique toppings and distinct local flavor profiles.

 Once you have tried them all, you can cast your vote to crown the winner of the coveted People's Choice Award.

 With non-stop live music performances rocking the main stage, ice-cold drinks flowing all afternoon, and every single dollar raised directly funding vital community nursing scholarships, 

educational grants, and local non-profits, this premier food festival delivers an unbeatable weekend experience.