Ever have one of those late-night hankerings for some yummy dessert and wonder where to go? Well, there’s the 24-hour The Trading Post in Islamorada.

Chatting with Betsy Jacocks and her son Michael Mooney brings out the history of The Trading Post, the adjacent Village Square property. And with the history come some fun things they have planned for the rest of this year into 2022.

Jasocks’s parents initially bought the store in 1966 for $32,000. Her parents had owned an iron ore mine and lost everything when Fidel Castro took over. Like many other Cubans, they moved here to start over. 

One day, her father was in the Keys working in the store doing their inventory when he heard the owner say, “I can’t wait to get out of here. I want to sell this place.” The original owner had opened the store so his wife would have a decent place to go grocery shopping.

Betsy then went to college in Louisiana to be a vet but ended back in the Keys after graduation. 

In 1990, Betsy bought The Trading Post from her mother for quite a bit more. Betsy said with a smile and a chuckle that when she found the original paperwork, years later, she called her mom to renegotiate. Her mom sweetly said, “Dear- Business is business,” and hung up on her.

Years later, their business is still thriving, with exciting updates on the way.

They are currently creating a walk-in Beer Cave where they will have the coldest beer — jacket required? In addition, the produce section is being updated and adding even more options. They are excited to be supporting South Florida farmers by adding in even more local produce. Next year, they are planning an extensive remodel. 

Family owned since 1966, The Trading Post is a one-stop shop for cold beer, fresh meats, desserts and more. WEEKLY FILE PHOTO

The deli is a No. 1 sales driver. Michael and Betsy were adamant that their prepared food is always “Homemade, fresh, nothing comes out of a box.” Adding in, “That’s one thing we will never give up or change.”

They get a good push of traffic around 9 p.m. and then again at midnight to 1 p.m. for that late-night snack crowd. It’s important to know where to go for some delicious desserts. (This is the part  when I started drooling over their bestselling Mississippi Mud Pie, Reese’s Pie, Key Lime Pie, chocolate cake, tarts, and more.)

The Trading Post is not only a full-service 24-hour grocery store, but also the perfect place to order food for football game day, an event, party, or as Michael said, “if someone wants to order a platter of sandwiches all for themself,” they are happy to help.

And they have varying fresh daily lunch specials. When asked what their favorite meal was, they both responded in unison, “The chicken salad.” Betsy admitted she doesn’t have a passion for cooking, which concludes that their food options have to be top-notch if that is the owner’s primary food choice for the past 30 years.

In addition, Mooney plans to increase the number of items they offer in their gift section. The gift items cater to locals and tourists as they are not “Keysee” but still smaller for a fun impulse, a gift, or stocking stuffer for the upcoming holidays. Some items are Paddywax Candles, Corkcicle, cocktail napkins, and the fun line Blue Q.

One last fun fact: The family lived in the house behind The Trading Post, which is now Miss Monroe, for 20 years. 

Besides Miss Monroe, there are several other must-visit businesses on the property — Bookee Sue Botanics, Bad Boy Burrito, and Café Moka at The Village Square. In addition to the success of those businesses, Betsy said, “They are all great tenants and get along nicely, like one big happy family.” 

It sounds like the perfect place to stop. Oh, and don’t forget your dessert.

Next up for The Village Square is Halloween festivities on Saturday, Oct. 30. Tickets will be on sale at the door. In 2022, there will be a new event called “Keys Concerts by Candlelight,” which will be a full sit-down dinner and drinks monthly January through April.

Follow on FB @thetradingpostofislamorada or IG @tradingpostislamorada to keep up to date.

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Melinda Van Fleet is a Confidence & Peak Performance coach, bestselling author of Confidence Mastery for Couples and Life & Love Lessons, and speaker, who works with businesswomen who desire to develop the confidence to believe in themselves, take action, and get results. Melinda is the host of two podcasts, The Good Karma Success Coach and Creating Confident Content. You can connect with her on FB, LI or IG melinda_vanfleet.