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City of Longwood

Wekiva Country Club

Longwood Historic District

Wekiva Springs State Park

Big Tree State Park

Of all Seminole County’s municipalities, Longwood, population 13,700, has the most history to preserve, and has done the best job of preserving it. But it’s still a modern place, with a plethora of exclusive country club communities, office parks and shopping centers.

In 1873 a New Englander named Edward Henck homesteaded a tract of land that he named Longwood, after a Boston suburb he had helped plan.

Henck was also the town’s first postmaster and its first mayor. And in what may have been his spare time, Henck co-founded the South Florida Railroad and built a line connecting Sanford and Orlando, which enabled Longwood to boom as a citrus- and lumber-shipping center as well as a winter resort destination.

But as crucial as Henck was to Longwood’s development, it was a carpenter named Josiah Clouser, a Henck employee, whose legacy is most visible. Clouser, a Pennsylvanian, constructed most of the buildings still standing in Longwood’s remarkable historic district, a two—block area on Warren and Church avenues near the intersection of C.R. 427 and S.R. 434.

Popular annual events include the Longwood Arts and Crafts Festival, held the weekend before Thanksgiving, and the Founders Day Spring Arts and Crafts Festival, held in March.

On the outskirts of the city; toward neighboring Apopka in Orange County is Wekiva Springs State Park. And on General Hutchinson Avenue is Big Tree State Park, home of “The Senator,” said to be the oldest and largest cypress tree in the state.