More Trick than Treat
Compiled and written by Marcy Shortuse
News clips from the Fort Myers News Press
Halloween is one holiday that Boca Grande’s
children have always looked forward to.
While the annual Halloween Carnival is
still going strong after decades, and there are
almost always costume parties to be had, there
is little trick-or-treating here with the exception
of the annual Halloween Walk of the downtown
businesses, sponsored by the Boca Grande Area
Chamber of Commerce.
Back in the olden days, the island’s children
found other ways to entertain themselves on
this particular holiday of spooks and skeletons,
ghosts and goblins. They would stay up as
late as they could to try to catch a glimpse of
“The Headless Woman,” who is rumored to be
Princess Joseffa (Gaspar the pirate’s lady love
who spurned his affection, so he beheaded her)
anywhere from Journey’s End on 18th Street to
Banyan Street, to down by the Port Boca Grande
Lighthouse.
Another part of a typical Halloween in Boca
Grande years ago, though, was all about mischief
… the “trick” more than the “treat,” you could say.
Back in the early part of the 1900s, Miss Rachel
Lamberson was the target of many pranks – often
on Halloween – pulled off by none other than the
original “Bad Boys of Boca Grande,” Dumplin’
Wheeler and Jackie Sullivan, and several others.
Back then, Halloween was an opportunity to
pull out all the stops on mischief … and you
better believe the stops were pulled out as far
as they could go. Many of the pranks involved
Miss Rachel’s car, a little Crosley model with a
propeller on the front. Because these were some
of the fi rst subcompact cars ever made, it wasn’t
too diffi cult for a large group of kids to pick
one up and move it around. Miss Rachel often
resorted to chaining her car to a tree to try to
thwart the children’s plans.