%20(4).png)
What’s Happening Around Key West This October: Coffee, Fantasy Fest & a Local Landmark in Transition
What’s Happening Around Key West This October
October is always one of the most interesting months in Key West. Summer starts giving way to busier streets, seasonal residents begin returning, restaurants and businesses gear up for the season, and then Fantasy Fest arrives and turns the island upside down for ten days.
Here are a few Key West stories that caught my attention as we head into October 2026.
Baby’s Coffee Is Back in Old Town
If you’ve spent any time driving between Key West and the Lower Keys, you probably know Baby’s Coffee at Mile Marker 15. Now you don’t have to leave Key West to get it.
Baby’s recently opened a new location at 418 Fleming Street, bringing the longtime Keys coffee company back to Old Town. According to Keys Weekly, the business’s coffee roots date to 1991 on Duval Street, before its move to MM 15 in 1995.
The new Fleming Street shop is open daily, and the owners are putting a particular emphasis on locals, including online ordering and priority pickup through a Dutch door on Bahama Street.
I love seeing longtime Keys businesses expand while still keeping their local identity.
Fantasy Fest Is Already Taking Shape
Fantasy Fest officially runs October 16 through October 25, 2026, with this year’s theme, “Musical Icons and Iconic Musicals.” The main Fantasy Fest parade takes place Saturday, October 24.
But what visitors see on Duval Street is only the finished product.
One recent Keys Weekly story followed a local team that started planning its 2026 float just one month after last year’s Fantasy Fest. Their entry, “OzFest Key West: The Emerald Tour,” mixes The Wizard of Oz with Ozzy Osbourne and is expected to include a float crew plus dozens of costumed walkers.
That is one of the things I love about Fantasy Fest.
Behind all the parties and costumes is an enormous amount of local creativity, construction, planning and teamwork.
Goombay also returns to Bahama Village on October 16 and 17, with food, arts and crafts and live music from noon to midnight, according to the official Fantasy Fest schedule.
Is Key West’s “Million Dollar Bar” About to Change?
Another local institution may be entering a new chapter.
Don’s Place, the longtime neighborhood bar at Truman Avenue and Grinnell Street, is under contract after being listed for $3.375 million, according to Above the Fold’s September 30 report. The bar has earned the nickname the “Million Dollar Bar,” although Key West real estate values have obviously moved well beyond that number.
What happens next is still uncertain. The report does not establish the buyers’ future plans, so it remains to be seen whether Don’s continues largely as people know it or the property takes on a different use.
For anyone who has lived in Key West for a while, stories like this are interesting because our real estate is tied so closely to the places people remember. A building is rarely just a building here.
October Is Just Getting Started
And those are only a few of the things happening around town.
The Key West Farmers Market continues at Truman Waterfront, First Fridays on Fleming returns, and the calendar gets progressively busier as we head toward Goombay and Fantasy Fest.
I’m going to continue sharing local happenings along with my Key West real estate updates because knowing this market is about much more than knowing what homes are for sale. It’s also about knowing the neighborhoods, businesses, people and traditions that make Key West what it is.
See you around the island.
Comments