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This Month in History: The story behind ‘Tom’s Follies’

By Staff | Apr 2, 2014

Readers of my column may recall that Tom Phillips purchased land on Pine Island in the 1930s and developed Tom’s Town. Today we call that area Pine Island Center.

In later years Phillips would also develop St. James City and assist in developing Flamingo Bay. Not many people are aware that Phillips partnered with Lee County to dig a tunnel under Pine Island Sound connecting Pine Island with Sanibel.

In 1938, Phillips purchased a large track of land at Woodring Point on Sanibel. If you look at a map of the area you will see that Woodring Point is directly across the sound from St. James City. Phillips wanted to build million dollar homes on his Sanibel property. This was before all of the mansions located on Sanibel today. Phillips realized though that few people would purchase on Sanibel if the only means of getting to the island was by the ferry at Punta Rassa. So, he offered Lee County to finance half of the cost of the tunnel if they would sell and guarantee bonds to cover the other half of the funding.

The only request from Phillips was that Lee County name the tunnel “Tom’s Tunnel.”

On April 1, 1939, work started on the project. The opening was dug near the end of Sanibel Boulevard in St. James City, but not at the very end. The digging went smoothly and 21 months later the tunnel emerged on Sanibel, but in “Ding” Darling National Park.

Phillips had hired an engineering firm from Sanibel to plot the direction of the tunnel. Well, these people on Sanibel did not want the “riffraff of Pine Island,” as they called us, invading their pristine island. So the engineer plotted the digging line to be off by one degree. By the time the tunnel reached Sanibel, it was off by several hundred yards to the west of where it should have emerged.

Because the tunnel exit was in the middle of a national park, Phillips could not build a road to connect the tunnel with his property.

By now the money had run out and the United States was about to enter World War II. The project was canceled and Phillips sold his property on Sanibel and concentrated on developing more of Pine Island.

When Phillips developed St. James City, many years later he filled in the entrance to the tunnel and sold the property. There is a home on that property today. I cannot reveal which house it is on Sanibel Boulevard out of respect for the owner. But if you drive down there you will see that one home distinctly leans to the right where the ground under it had settled.

On Sanibel, in the “Ding” Darling Park, there is a plaque commemorating Tom’s Tunnel at where it emerged. It was erected there by that same engineering firm that had plotted the tunnel for Phillips. The plaque simple says “Tom’s Follies.”

A special thank you to Ben Lyon of the “Ding” Darling Historical Society for his research that contributed to this article.

For more history of Pine Island, visit the Museum of the Islands, Tuesday through Saturday, 11 a.m. to 3 p.m., and Sunday, 1-4 p.m.

The museum is conveniently located next to the Pine Island Library at 5728 Sesame Drive off Stringfellow Road. Call 239-283-1525.

Tim Knox is museum historian at the Museum of the Islands.