Mr. Mac and life along Caroline Street: The roots of Old Key West

The railroad brought the world to Key West

When the Overseas Railroad, built by Henry Flagler, began running to Key West in 1914, the island suddenly felt closer to the rest of the world. The line — part of the ambitious Florida East Coast Railway — ended at the waterfront near Caroline Street. Travelers arriving by train often lingered in town while awaiting steamship connections to Cuba and beyond.

At the same time, car ferries from the Upper Keys unloaded vehicles at the Bight. (There would be no continuous highway to Key West until 1938.) The result was a steady stream of visitors walking directly past a growing cluster of small shops selling shells, coral, sea fans and maritime curiosities. These storefronts weren’t just tourist stops — they were windows into the working life of the island.

The birth of Mac’s Sea Garden

In the winter of 1921, William “Willie” McHugh — known locally as Mr. Mac — opened Mac’s Sea Garden. A former cigar maker, he had lost his livelihood when factories relocated to Tampa in the early 1900s.

With seven children to feed, Mr. Mac turned to the water. Like many Keys families of the time, he became a sponger, working the narrow channels between islands and collecting what the sea provided.

His shop inventory read like a catalog of the ocean floor: sea feathers, coral, conch shells, glass floats, demijohn bottles from wrecked sponge boats, and objects tangled in mangrove roots. Family stories tell of a sponge once hauled aboard with a pirate sword embedded in it — a reminder that Key West’s waters hold centuries of layered history.

McHugh’s ability to speak Spanish, learned during his cigar factory days, allowed him to connect easily with Cuban and Latin American visitors. Nearly all his merchandise was displayed outdoors, packed away nightly against storms — a daily rhythm that mirrored the island’s dependence on weather and tide.

Street dances during the Depression

The Great Depression slowed tourism, but creativity kept the street alive. Through a Works Progress Administration program, Mr. Mac organized a string dance band and hosted public dances several nights a week along Caroline Street, a historic 0.5-mile street that runs from Whitehead Street to Grinnell Street in the Old Town area. Music spilled into the warm night air between Margaret Street and Grunt Bone Alley, turning hardship into community celebration.

Mr. Mac ran his shop until 1938 — the year the Overseas Highway finally connected Key West to the mainland after the railroad’s destruction in the catastrophic 1935 hurricane. His son, C.B. McHugh, later known as the “King of the Spongers,” continued working on the water and advocating for the protection of sponge grounds and the pink conch well into the late 20th century.

The modern Mac’s Sea Garden pays homage to those early curio shops that once lined Caroline Street. Even the playful signage — “Woolworth of the South” and “Nickels and Dimes” — reflects Mr. Mac’s original flair for promotion.

Why stories like this still matter

Key West isn’t a manufactured destination. It’s a living museum shaped by working families, immigrant communities and maritime trades. Walk a few blocks in any direction and you’ll find echoes of railroads, wrecking salvages, cigar rollers, sponge fleets, and Caribbean influences that still define the island’s character.

Known as one of the island's most scenic, Caroline Street features 19th-century "conch houses," luxurious restored homes, and close proximity to the Historic Seaport and Duval Street.

Staying in a historic home deepens the connection to the island’s past. At Historic Key West Vacation Rentals, our collection of thoughtfully preserved homes places you inside neighborhoods where these stories unfolded. Instead of observing history from a distance, you live among it: morning coffee on a wraparound porch, evening walks past century-old cottages, salty air drifting in from the harbor that once welcomed railroad travelers and sponge boats.

Many of our properties retain original architecture, woodwork and layouts that date back to the same era as Caroline Street’s curio shops. When you wake up in a restored conch house, you’re not just visiting Key West — you’re inhabiting its timeline.