The Farmers Markets On Dearborn Street

First Thursday In October - 2025 

Till:  Last Thursday In May 2026

Every Thursday 9am to 1pm

  The Market On Dearborn 

 232 W Dearborn St., Englewood, Fl. 

First Thursday In October - 2025

Till:  Last Thursday In May 2026

Every Thursday 9am to 1pm

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

The Artist Colony Outdoor Gallery

 Artists Display & Sell their Original at our Outdoor Gallery 1st and 3rd Wednesday Oct-April 

10am - 3pm

The Open Studio

Open Mic Tuesday

Concert Series Thursday

4pm - 8pm

380 Old Englewood Rd

Englewood, FL 5 - 8

It is an Open Air Party thrown every Tuesday. The Party is free and everyone is invited, even pups .

Coolers are even welcomed. We have enough room to spread out. The Garden is something very unique. There is no place like the garden. 

We have some chairs but feel free to bring your own.

Musicians come from near and far to play for all at the Party. 

Summertime usually is filled with only local players.

All genres, all talent levels welcome. We have some great local musicians that share the stage.

Happy faces found here!! Come on down and let's see your smile.

Let's celebrate another wonderful Tuesday in the Garden!

Musicians - sign up for mic time. Up to 3 songs and we will have a rotation for a second time up ( summer is like this) Bring your instrument. E Drum and Congas available.

Plant Based Food Is Available

Menu is something different every week.

WEDNESDAYS@5

  WEDNESDAYS@5 features the best local musicians and showcase their talents 

at

The Old Florida Outdoor Center and Gallery at 463 W Dearborn St. in Englewood 

 All musicians, songwriters, singers, dancers, poets, comedians, storytellers, eaters and drinkers welcome! 

All ages and abilities.

 Stage, microphone, and amplification provided. Hosted by Gary Louis every Friday 5:00 - 9:00+ at Culture Coffee.

405 W.Dearborn Street  

THE GREAT MR. SWINDLE'S TRAVELING PECULIARIUM AND DRINK-ORY GARDEN®

Get ready for an experience that’s delightfully inappropriate, shockingly fun, and utterly unforgettable! The Great Mr. Swindle’s Traveling Peculiarium and Drink-Ory Garden®—a spectacle so wildly inappropriate and uproariously funny, it defies description. Hosted by Mr. B.S. 

Swindler, AKA Mr. Swindle—this 90-minute extravaganza unfolds under a hypnotical Big-Top, where unbelievable feats, absurd comedy, and the unexpected come together to create one unforgettable evening.

ELIXIR’S DRINK-ORY GARDEN

Join us an hour before showtime at Dr. Elixir’s Drink-Ory Garden, where you can indulge in perplexing potions, bitter brews, mischievous medicines, and savory snacks—a tantalizing prelude to the wildly entertaining evening ahead!

LOCATION

Under The Boutique Big Top at Pioneer Plaza
325 W Dearborn St
Englewood, FL 34223

  The Lemon Bay Historical Society's annual Cracker Fair for 2026 is scheduled for

 Saturday, February 14, 2026. 

10am - 4pm

Event details

• Date: Saturday, February 14, 2026.
• Location: Pioneer Plaza in Englewood, on Dearborn Street.
• Admission: The event is free to the public.
• Activities: The Cracker Fair typically includes live performers, food and craft vendors, artists, authors, and demonstrations. Past events have featured whip-cracking demos by Bit of Hope Ranch and live animals from the Peace River Wildlife Center.
• Culmination of Lemon Bay Fest: The Cracker Fair marks the end of "Lemon Bay Fest," a week-long series of local history events organized in conjunction with the Englewood libraries. 

 The Cracker Fair typically features a wide variety of activities, entertainment, and vendors celebrating "Old Florida" heritage. Typical Activities and Entertainment

• Live Music: The fair usually includes live performances of folk, blues, country, bluegrass, Americana, and classic rock music.
• Demonstrations: A key part of the fair is traditional "Cracker" skills demonstrations, which have included whip-cracking by Bit of Hope Ranch, swamp cabbage preparation, and cast net throwing.
• Animal Exhibits: Organizations like the Peace River Wildlife Center often bring live animals for educational presentations.
• Lemon Dessert Baking Contest: The event hosts a popular baking contest where participants present their best lemon-themed desserts.
• Kids' Zone: There is usually a dedicated area with activities for children. 

Typical Vendors and Booths

• Food Vendors: A variety of food options are available, ranging from local cuisine to classic fair food.
• Artists and Authors: Local artists and authors, particularly those focusing on local history, often have booths.
• Crafts and Local Merchants: Numerous stalls feature hand-crafted goods and merchandise from local businesses.
• Informational Booths: Community and non-profit organizations often set up informational booths. 
• 
  

The overall atmosphere is a lively celebration of local history and culture in Englewood's Pioneer Plaza.
 

 This year the event will be held at the Englewood Elks Club. 

 This year the event will be held at the Englewood Elks Club. 

 Feb 27th – Mar 1st

If relaxing, having fun, enjoying good food, and listening to great live music over the weekend sounds like your perfect plan, then we have exactly what you need at the 7th Annual Englewood Seafood & Music Festival. 

This year the event will be held at the Englewood Elks Club.

Dates of the festivities are 

February 27th – March 1st, 2026. 

The fun and relaxation start 

Friday evening from 4pm-10pm, continuing Saturday 11am-10pm and Sunday 11am-6pm. Admission is FREE! 

The event is produced by Paragon Festivals in association with Sarasota County.

Choose your foods from a diverse menu of seafood, meat, and vegetarian dishes, all cooked fresh onsite by local restaurants and food purveyors. Seafood dishes are prepared using only the freshest local and sustainable ocean resources from the Florida Gulf Coast. 

Select from a variety of side dishes and, of course, awesome desserts! Liquid refreshment includes selections of alcoholic, non-alcoholic, and fruit drinks, along with sodas and bottled water.

While immersed in great food, listen to some of Florida’s top musical groups from genres such as R&B, blues, jazz, rock, and Caribbean sounds. The entertainment schedule will be posted as the festival date approaches. 

Last year’s performers included The Billy Rice Band, Kara Nally Band, K-Luv & United Funk Foundation, Trey Wanvig Band, Dr Dave Band, Annika Chambers Deslauriers & Paul Deslauriers, 22N, Maiden Cane, Jack’D Up, Kettle of Fish, and Gas House Gorillas.

During breaks between performances, enjoy shopping at a marketplace of fine arts, crafts, and select fine products and food items.

This is Plan A! All you need to do is come to the event and partake in all the festivities! Remember: YOU are the most important ingredient and have earned this time! We look forward to seeing you and having you be part of this growing, vibrant event in Englewood.

No outside food or drinks permitted.

3rd Annual Small Town Boots & Brews Country Music Festival – Englewood, FL

Pioneer Park, Dearborn St, Englewood, FL

Date: Saturday  March 21, 2026  

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 3rd 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.  

Date: March 21, 2026  

Location: Pioneer Plaza 325 W Dearborn St., Englewood, FL 34223  

Live Music from Amazing Country Artist  

Enjoy a full lineup of top-tier country music acts performing live on stage, bringing you the best of traditional country, Southern rock, and honky-tonk favorites.

 Last years artists featured:  

Pure Country of Southwest Florida  – A local favorite delivering high-energy country hits!  

The Winters Brothers Band  – A legendary Southern rock band you won’t want to miss.  

Also performing:  

Everett Ferrell  Flatwater  Bittersweet Saloon Marty Moss & The MossTones   

CALLING ALL GRILL MASTERS, BURGER LOVERS & PARADISE HEROES!

SATURDAY APRIL 4th,2026 

The Englewood Sunset Rotary Impact Club is turning up the heat for the THIRD ANNUAL 2026 Burgerfest in Paradise! 

Have what it takes to claim the title of Best Burger in Paradise? 

We’re looking for fun, community-minded GRILLERS ready to flip, sizzle, and serve for a great cause — raising funds that go right back into our local community.

 Whether you’re a backyard BBQ legend, a restaurant pro, or just love seeing smiles around the grill, this event is your moment to shine!

 100% of proceeds support local programs, families, and service projects that make Englewood the paradise we’re proud to call home.

 Join us as a griller, sponsor, or volunteer!

Let’s make 2026 the biggest, juiciest Burgerfest yet.

 Englewood Sunset Rotary Impact Club

email RotaryImpactFL@gmail.com for details