We found three Christmas markets and winter events in and around Fort Myers–Naples with 2026 dates posted: three holiday markets. Two are free to get in. They’re in Naples and Fort Myers. Each card has the dates and hours, what it costs to get in, and notes on strollers and things for little kids.
By date
Tap one for hours, prices, stroller notes and what’s there for little kids.
Holiday market · Public market Saturday, Nov 7 (preview party Friday evening) · Trinity-by-the-Cove, 553 Galleon Dr.4DecFriChristmas on 5thHoliday market · to Dec 5 · Fifth Avenue South4DecFriHoliday Artisan Market (December Art Walk)Holiday market · Friday, Dec 4, 5 to 9 p.m. · First St. and Hendry St.Nothing matches that filter yet.
Markets
Dates, hours and prices come from each organizer’s, venue’s or city’s own page.
Trinity-by-the-Cove, 553 Galleon Dr. · Naples, FL
Good to know: A church holiday market with local vendors, homemade jams and jellies, gingerbread treats and a thrift room. Proceeds support outreach ministries.
Fifth Avenue South · Naples, FL · downtown
Good to know: Market details are still to come on the organizer's page.
First St. and Hendry St. · Fort Myers, FL · River District
Good to know: Art, crafts and music on closed downtown streets.
Before you go
TimingGo when it opensWeekday afternoons and opening hour are the least crowded, which makes a stroller much easier.
DressLayer upOutdoor markets get cold after dark. Mittens and a blanket for the stroller help.
StrollerCheck the stroller noteSome markets get packed on weekend evenings. A carrier can be easier there.Keep planning
November: things to do in Fort MyersEvery dated listing for the month, by weekDecember: things to do in Fort MyersEvery dated listing for the month, by week
Free things to do in Fort MyersFree days, free events and places that never charge
Thanksgiving weekend in Fort MyersParades, turkey trots and what’s open on Thursday
Christmas parades in Fort MyersParades and tree lightings with dates and start times
The Nutcracker in Fort MyersBallet and touring shows, sensory-friendly flagged
This week in Fort MyersDated outings for ages 0–6, checked every ThursdayGood questions
Christmas Market at Trinity-by-the-Cove at Trinity-by-the-Cove, 553 Galleon Dr.: Sat, Nov 7, 2026. Christmas on 5th at Fifth Avenue South: Dec 4 – Dec 5. Holiday Artisan Market (December Art Walk) at First St. and Hendry St.: Fri, Dec 4, 2026.
Each listing comes from the venue’s or organizer’s own page and links to it. We only list a date, time or price when that page shows it, and anything we can’t confirm stays off. These were last checked Oct 30, 2026, and we recheck them every week through December. How we choose and check.
One short email every Thursday evening with the best things to do with little ones in Fort Myers that weekend, holiday markets included.
