Big Pine Key's Holiday Season Starts in Daylight and Ends at a Lit Bridge

Three street numbers on Overseas Highway and one on Atlantis Drive hold most of Big Pine Key's holiday season. They are 30250, where the flea market is; 31020, the Lower Keys Chamber of Commerce grounds at Mile Marker 31; and 31009 Atlantis Drive, the county's community park. The fourth date is farther down the highway at Bahia Honda State Park, 36850 Overseas Highway, where the season ends with luminaries lighting the garden and the Old Bahia Honda Bridge.

Read in order, the calendar runs from weekend market days to a nine-to-three art festival, then a tree lighting at 7 p.m., then an evening walk at the state park. All four are run by groups that are already part of island life all year: a market owner, the chamber, Monroe County Parks and Beaches with the Lower Keys Rotary Club, and a state park.

The Flea Market Reopens This Saturday, With Upgrades

The season starts this Saturday. The Big Pine Key Flea Market lists Nov. 14, 2026, as opening day. Its vendor information books seasonal spaces from Nov. 14 through April 25, 2027, so the market keeps going for months after the holidays end.

According to the market, it has had some recent updates. The bathrooms have been completely renovated, every seasonal vendor has a new tent or canopy, and the grounds have been improved. The market calls itself "the largest and most diverse shopping experience in the Keys" and pitches itself as part of your weekend plans. The Lower Keys Chamber member directory lists the business as Big Pine Flea Market, LLC, with Joe Marrama. Keys Weekly covered the market's 2019 reopening under his ownership, and that renovation also covered the restrooms.

The market's homepage puts the food news first: "the Fish Fry is here!" The Big Pine Key Famous Fish Fry heads a food list that also includes:

• Johnny Coconuts
• Mini donuts
• Homemade French pastries
• Fresh produce
• Amy's Ice Cream

The shopping side is the mix you would expect from a Keys market. It has clothing and hats, jewelry, sunglasses, wood carvings, fishing equipment, art and antiques, plants and flowers, health and beauty products, patio furniture and home décor, and boutique clothing. Plants and patio furniture are on the list, so you can plan a porch refresh around a market weekend before the guests arrive.

Two Weeks Later, the Chamber Grounds Fill Up the Night Before

The Saturday after Thanksgiving, the action moves up the highway to the chamber grounds at Mile Marker 31. The Lower Keys Chamber of Commerce holds its Island Art Festival there on Nov. 28, from 9 a.m. to 3 p.m.

The chamber's 2026 vendor application shows how the day takes shape. Vendors who have turned in a completed application and signed waiver can set up tables and tents early, starting Friday at noon. Everyone else sets up Saturday from 7 a.m., and vendor vehicles have to be off the grounds by 8 a.m. There is no electricity on site, so only ultra-quiet generators are allowed. The chamber also asks vendors to bring a canopy or umbrella for shade.

The chamber's festival page describes handcrafted goods from artisans "from near and far." In an earlier preview, Keys News described the annual festival as typically drawing more than 50 artisans and vendors. Their work included jewelry, stained glass, paintings, candles, soaps, wearable art and locally produced foods, and some vendors gave demonstrations.

If you'd rather be behind a table than in front of one, booth spaces are priced as donations to the chamber:

Apart from early registration and payment, the chamber assigns spaces in the order applications arrive. Vendors bring their own tables, chairs and racks, and the chamber rents tables for a $15 donation each. Food vendors list their menus ahead of time so the chamber can avoid duplicate menus. Donations are nonrefundable. You can register online at the chamber's site, or by mail to 31020 Overseas Highway, Big Pine Key.

Atlantis Drive Lights a Tree for the Second Year

Six days after the festival, the season moves into the evening for the first time. On Friday, Dec. 4, Monroe County Parks and Beaches and the Lower Keys Rotary Club hold the second annual Big Pine Key Community Park Tree Lighting at 31009 Atlantis Drive.

This is only the event's second year, which makes it the newest thing on Big Pine's December calendar. It's free and family-friendly. Gates open at 6 p.m. and the tree is lit at 7. The county lists a winter village, holiday games, arts and crafts, letters to Santa, a holiday hayride, live music and entertainment, plus s'mores and hot cocoa. For details, the county's number is 305-453-8748.

The park's street number is 31009, and the chamber grounds are at 31020. That puts the art festival and the tree lighting at almost the same address number, with the flea market's 30250 just below them. Three of the season's four dates fall in that short run of numbers.

The Last Stop Is at Bahia Honda, Free After Sunset

The final event takes the season farther down the highway and later into the day. On Thursday, Dec. 17, Bahia Honda State Park holds its Luminary Walk from 5:30 to 7:30 p.m., based at the Loggerhead Parking Lot.

The Florida State Parks event listing describes it like this:

"Bahia Honda State Park's Luminary Walk is an event that invites the local community to come enjoy the park and craft activities after hours. The garden and iconic Old Bahia Honda Bridge are lit up for the event."

Normal park fees apply before sunset, and no admission is charged after sunset. The park also runs a food drive for a local community food bank that night, and visitors are welcome to bring nonperishable food. The Friends of Bahia Honda State Park list the night on their calendar as the Luminary Walk and Food Drive.

Art festival booths are paid as donations to the chamber, the tree lighting is put on with the Rotary club, and the Luminary Walk ends the season with a food drive. A cooler with a few cans of soup and a bag of rice is all it takes to join in at the last stop. Bahia Honda's address is 36850 Overseas Highway, Big Pine Key.

If you're planning December in the Lower Keys or hosting family on Big Pine for the holidays, the team at Bascom Grooms Real Estate has been part of this community since 1999. We're happy to share what we know about the stretch between Mile Marker 31 and the Bahia Honda bridge. Contact Us, and we'll see you at the Loggerhead lot on the 17th with a can for the food drive.