The Best of Old Florida – West Dearborn Street and Olde Englewood Village


By Gabriele Walkow

For a slower, easygoing pace of life, Olde Englewood Village and West Dearborn Street, on Florida’s Gulf Coast, offer the best of Old Florida. Charming and laid-back, visitors are greeted by a down-home friendliness and casual ambience ideal for making treasured vacation memories. First settled in 1878, this former fishing village is quickly becoming a go-to destination.

Travel back to Old Florida on West Dearborn Street and Olde Englewood Village

Home to delightful restaurants—many with al fresco dining—cozy cafes, unique gift shops, gorgeous art galleries and beautiful boutiques, Englewood’s historic downtown area is a throwback to the Main Streets of yore. Hunt for antiques and vintage treasures, purchase paintings, photos and other pieces by Florida artists, and pick up some jewelry and other gifts for friends back home.

Visitors will be enchanted with quaint and historic West Dearborn Street. Designated a Sarasota County Community Redevelopment Area (CRA), West Dearborn Street is the perfect mix of small town atmosphere complemented by contemporary touches. Old Florida charm is blended with new ideas.

A must-see attraction on West Dearborn Street, the Old Florida Outdoor Center and Gallery inspires through art and adventure. Book a kayak or paddleboard tour, shop for lovely local artwork, participate in a fun art class and learn about fly-fishing, all in one spot!

The Old Florida Outdoor Center and Gallery inspires through art and adventure

Featuring excellent entertainment in the form of drama, comedy, thrillers and showcase productions, the Lemon Bay Playhouse also fronts on West Dearborn Street. Further along, a neighborhood of historic homes provides a glimpse into Englewood’s past.

Make a toast to a day of Old Florida fun and savor dinner and a drink at Mango Bistro or Vino Loco. These two stylish spots pour wines from around the world to pair with small plates, salads and other delectable dishes. Dance the night away at Englewoods on Dearborn. This hot spot features delightful dining, cool cocktails and award-winning blues artists.

In addition to an exciting roster of special events, the Village is home to several popular ongoing events. The Englewood Farmer’s Market is a picturesque affair every Thursday from 9 a.m. until 2 p.m. October through May. Held the first Saturday of every month at 5 p.m. Cruisin’ on Dearborn Street welcomes hundreds of cars and car enthusiasts to this free vintage and antique car show. Discover Englewood’s rich and colorful history during Lamp House Tours and Englewood Historical Museum Tours.

For more information on this Gulf Coast treasure, visit

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