Englewood is the only town in Florida I know that resides in two counties – Sarasota and Charlotte County. The area was settled in the late 1800s by pioneers like William Goff, who opened a trail from El Jobean to Vineyard (nowadays Dearborn Street), and Lorin Ainger, who set up a store to serve area fishermen. In 1896, the three Nicolas Brothers started a 24-four block community and named it Englewood after their Illinois hometown (the event is celebrated in Englewood every Labor Day weekend). The town remained agricultural until the 1940s, since the Tamiami Trail passed east of the peninsula.
Little remains from those pioneer days. The original center of Old Englewood is the corner of Old Englewood Road and Dearborn Street, where, at 2 Old Englewood Rd., you can see the Rickards’s Guest House, built in 1896. For you history buffs, the house that was once the winter home for Ohio State professor Edward Sommermeir can give you feelings of those bygone days. Today, Dearborn Avenue offers quaint village shops for that special find, a place for brunch, and somewhere to get groceries.
To meet the charming and laid-back present, let’s take a side trip off Old Englewood Road. Turning west on Stewart would lead to Lemon Bay Park, Sarasota County's newest nature complex (with a butterfly garden, picnic sites, and nature trails). Down the road, on the Lemon Bay shore south of Dearborn Street, Indian Mounds Park offers a public boat ramp, a historic nature trail, and picnic tables. Before crossing the bridge to Englewood Beach, you might want to drive along New Point Comfort Road, site of old cottages and the former Bass Biological Lab. Crossing the Tom Adams Bridge, turn left to notice the huge white Chadwick Beach Pavilion built in 1927, once the focal point of Steve Chadwick's cottage colony.
Today, Englewood is a town that thrives on its beaches, nature parks, cultural events, fishing, and boating.
The Englewood Sports Complex is excellent place for families, featuring lots of fields for amateur baseball, softball, and soccer, as well as tennis courts, playground, and picnic areas. San Casa Athletic Complex also draws a number of athletes, while the Trangaili Community Center features a teen center, meeting facility, and tennis courts.
Englewood hosts many activities for all to enjoy. Among them are March Madness Seafood Festival, Turtle Watch, September’s Pioneer Days festival (every Labor Day weekend, locals commemorate the pioneers who were responsible for its origin in 1896), Florida International Air Show, Manasota Beach Art Show, Englewood Rotary Fine Arts Festival, Boca Grande Tarpon Tournament (held in July), and Fourth of July fireworks.
The rainy season lasts here from June through September, with rain spread fairly evenly throughout those months. Thunderstorms tend to pop up quickly but also dissipate just as quickly, with the sunshine quickly returning. The winters are lovely, with warm afternoons and mild evenings and much less rain. Hurricane season generally runs August through October.