"The next day, there were four more waiting to be rescued!"
Casting for Cats posted that line in May, after its volunteers found a group of kittens living behind the Community Center in Founders Park. The nonprofit paid to have every one of them spayed or neutered. Then it went back for the next four. The same post points readers to the group's October backcountry tournament, which pays for rescues like that one.
In a story about stray cats you can see how Islamorada's fall comes back. It doesn't build slowly. It returns in one short window, from Thursday, October 15, through Sunday, October 18. Almost every piece of it runs through a few familiar places: Lorelei, Islander Resort, Whale Harbor, Morada Way and Founders Park. Much of the money raised that week stays in the Upper Keys.
Four Days, at a Glance
- Thursday, Oct. 15. Florida's stone crab season opens. That evening the Morada Way Art Walk runs from 6 to 9 p.m.
- Friday, Oct. 16. Casting for Cats holds its check-in and rules meeting at Islander Resort. Ladies, Let's Go Fishing starts its fall Keys seminar with a networking social.
- Saturday, Oct. 17. Casting for Cats anglers fish out of Lorelei, then go back to Islander for dinner and awards. The seminar spends the day on classes and hands-on skills.
- Sunday, Oct. 18. The seminar wraps up with optional fishing.
Thursday Opens Two Seasons at Once
Stone crab season usually gets its own coverage. This year opening day falls on the third Thursday of October, which is Art Walk night. So the first claws and the first busy evening of the fall season share a date.
According to the Florida Fish and Wildlife Conservation Commission's season announcement, harvest starts October 15 and runs through May 1, and the season closes May 2. Those dates come from the agency's 2025 release and follow the season's standard calendar. If you run your own traps off a dock, a few rules from that release apply:
- Claws must measure at least 2 7/8 inches.
- Plastic and wood traps, recreational or commercial, need an unobstructed escape ring of 2 3/16 inches.
- Recreational harvesters 16 and older must complete a free trap registration every year.
If you'd rather buy than trap, Islamorada Fish Company runs a restaurant and a retail market next to it, and says fresh Florida stone crab is sold at both while the season lasts. The company's own website lists different season dates on different pages, so call before you drive over on opening week.
That evening, the Morada Way Arts & Cultural District opens its galleries from 6 to 9 p.m. for the monthly Art Walk, with artists on hand, live music, food and drinks. The district's current studio list includes:
- Jessica Ann Art
- Limelight Studio + Gallery
- Taylor Hale Studio & Gallery
- Morada Way Clay, at 140 Morada Way
Each studio sets its own hours and access, and the district hasn't posted which venues will open on the night of the 15th.
Friday and Saturday Belong to the Flats
The weekend has two fishing events, and they work very differently. One is a competition that raises money. The other is a teaching event that fills up early. Both run out of docks most locals could find without a map.
| Casting for Cats Backcountry Tournament | Ladies, Let's Go Fishing Keys Seminar | |
|---|---|---|
| Dates | Oct. 16–17, 2026 | Oct. 16–18, 2026 |
| Home base | Islander Resort, with Saturday angler check-in at Lorelei | Tavernier Elks for classes and the Friday social |
| On the water | Backcountry catch-and-release | Whale Harbor |
| Format | Two-angler teams, bait, artificial and fly divisions | Friday social, Saturday classes, optional fishing Friday and Sunday |
| Status as of early October | Taking entries through the organizer | Inshore fishing full as of Oct. 4; classroom seats open |
Casting for Cats has opened its doors
Casting for Cats is a Florida-recognized 501(c)(3) that raises money for the Upper Keys' feral cats. For years the tournament was for women only. This year it adds co-ed and junior divisions. Under the 2026 entry form, a co-ed team is one male and one female angler. A two-angler team pays $600 to enter. Juniors ages 10 to 17 fish solo for $200 and aren't eligible for the boat prize.
The target species are permit, bonefish, tarpon, snook and redfish, all released after the catch, with bait, artificial and fly divisions. The website puts the Saturday awards dinner at 8 p.m. The printed brochure says 7:45. Confirm with the organizer before you make plans.
The junior division lets a 12-year-old who has grown up on the flats enter a real tournament with real scoring, and the entry fee pays for spay and neuter work on the same island. The Founders Park rescue is one example of where that money goes.
The seminar that filled its boats early
The Ladies, Let's Go Fishing program holds its Friday social and Saturday classes at the Tavernier Elks and fishes out of Whale Harbor. The organizer notes that Robbie's party boat isn't available for 2026 and points anglers to Miss Islamorada. The organizer's October 4 update said every inshore fishing slot for both days was taken. Classroom space was still available. If you live nearby and have wanted to learn knots, casting or how to read the backcountry, a seat in the classroom is still an option.
Lorelei Hands the Keys to People From Here
Saturday morning, Casting for Cats anglers check in at Lorelei. They'll be walking into a restaurant that changed its leadership this summer.
In August, Keys Weekly reported on Lorelei Restaurant & Cabana Bar's new management team, all of them already on staff:
- Mike Wilkinson, general manager. He has lived in the Upper Keys all his life, graduated from Coral Shores, and has nearly 20 years in hospitality, the last eight at Lorelei, where he has worked almost every position. He is also a longtime friend of the Lindback family.
- Ann Dotson, assistant general manager. She is marking 15 years at Lorelei and has a background in nonprofit management.
- Patrick Naughton, executive chef. A born-and-raised Keys Conch and Coral Shores graduate with more than 15 years of culinary experience, he spent a year in Lorelei's kitchen before taking charge of it.
The same report says the restaurant is still serving the favorites it's known for, including house-made conch fritters, the blackened snapper reuben, smoked fish dip, the Lorelei Sunset made with the restaurant's own vodka, the Key Lime Colada, and Key lime pie served traditional or frozen, with live music every night. A team that grew up locally and came up through the restaurant now runs one of Islamorada's best-known sunset spots. That fits the rest of the week, where most of what's on the calendar is homegrown.
Founders Park, a Week Later
After that weekend the calendar stays quieter until October 24. That evening, according to a Village of Islamorada alert posted October 1, the eighth annual Trunk or Treat runs at Founders Park from 6 to 8:30 p.m. It includes a costume contest, food trucks and pumpkin decorating, and parking costs $15.
Founders Park is also where Casting for Cats found the kittens in May. Saturday's anglers on the flats are paying for the kind of rescue that happened behind the building where families will park on the 24th.
Earlier in the month, the Islamorada Chamber calendar lists Oktoberfest on October 11. The calendar doesn't name a venue, so check with the Chamber before you go.
If an autumn on the water near the Islander, Whale Harbor or Lorelei has you thinking about a place of your own here, with dock access and room for the gear, The Cascone Team would be glad to help you look at the details, starting with the boat. Let's Connect.
This article is general information, not legal, tax or financial advice. Consult a qualified professional about your situation.
