Smallwood Store: Chokoloskee's 1906 Trading Post

Ted Smallwood's trading post

Chokoloskee Island sits at the ragged southern edge of the Ten Thousand Islands, a shell-mound island the Calusa built up centuries before anyone thought to put a store on it. Ted Smallwood arrived as a young pioneer in the 1890s and, in 1906, opened a trading post to serve the handful of families scattered across this remote stretch of coast — a place with no roads, no bridges, and no way in except by boat through miles of mangrove creeks and open bay. For decades the store was the only real supply line for this end of the Ten Thousand Islands: the place you came for flour, tools, cloth, coffee, and word of what was happening anywhere beyond the mangroves.

It’s worth sitting with how isolated that really was. Chokoloskee wouldn’t see a road connection to the mainland until decades later; before that, every sack of flour, every bolt of cloth, and every letter arrived the same way every customer did — by water. That single fact shaped everything about how Smallwood ran his business, and it’s the same fact that shapes the rest of the story you’ll find across our Local History pages: on this coast, the water was never a barrier. It was the road.

What makes the store worth a stop isn’t just its age. It’s that Smallwood built his business on relationships with everyone who lived and worked this water — Seminole hunters and trappers, gladesmen running trap lines through the backcountry, and pioneer families clearing small farms on the scattered high ground of the islands. That mix of customers, all arriving by water because there was no other way to arrive, is what turned a small-town general store into one of the most-cited chapters in Ten Thousand Islands history.

Seminole canoes and pioneer barter

Picture the scene the store was built for: a Seminole family paddling a dugout canoe across Chokoloskee Bay, loaded with otter and raccoon pelts, alligator hides, and maybe a haul of egret plumes from the plume-hunting years, pulling up at Smallwood’s dock to trade for coffee, cloth, ammunition, and tools. That kind of barter trade — hides and skins for hard goods — was the backbone of the store’s early decades, and Smallwood earned a reputation as an honest trader at a time when that wasn’t a given out on this frontier.

Pioneer families across the Ten Thousand Islands brought their own trade goods too: sugarcane and cane syrup, guavas and other produce grown on the thin patches of arable high ground, plus fish and furs from their own trap lines. Everything moved by water, because everything out here still does. That’s the same water our Ten Thousand Islands boat tours run through today — the same bay, the same channels, the same reason nothing out here has a road.

The building that wouldn't go down

South Florida hurricanes have flattened plenty of pioneer-era buildings over the past century, and Chokoloskee has taken direct hits from more than a few. The Smallwood Store survived them by design: it’s raised well above the water on wood pilings, a construction choice that let storm surge pass underneath instead of through the building. It’s the same logic that saved plenty of old Florida coastal architecture — build up, not just strong.

The store operated as a working business into the early 1980s before closing, then reopened as a museum run by Smallwood’s own descendants, who kept the original shelving, the ledgers, and the merchandise more or less as it was left. Walking through it today, you’re not looking at a recreation or a themed attraction — you’re standing inside the actual trading post, on the actual pilings, over the actual bay. That authenticity is rare on this coast, where so much pioneer-era building has been lost to storms, fire, or simple redevelopment.

The landing where Ed Watson was shot

The store’s history has a darker chapter too, and it’s the one that put Chokoloskee on the literary map. In October 1910, Ed Watson — a Chatham Bend planter suspected in a string of deaths among his own workers — came ashore at Chokoloskee by boat. A group of island residents, having heard the rumors and fearing for their own safety, confronted him right at the landing in front of Smallwood’s store. Watson was shot and killed on the spot. The story became one of the most retold in Florida frontier history, later fictionalized in Peter Matthiessen’s acclaimed novels about the Ten Thousand Islands. You can read the fuller account of that day on our Ed Watson history page — it’s the darkest tale this stretch of coast has to tell, and it happened on the same dock you can still walk out on today.

Visiting the store today

The Smallwood Store sits on Chokoloskee Island, a short causeway drive from Everglades City and a world away from Marco Island’s condos and beaches — even though it’s barely a boat ride apart. Inside, you’ll find the original trading-post shelving still stocked with vintage goods, historic photographs of Smallwood and the pioneer families who traded here, and displays on the Seminole trade relationships and the Ed Watson story. It’s a small museum, an unhurried one, and exactly the kind of place that rewards slowing down rather than rushing through on the way to somewhere else.

Most visitors reach it by car via the causeway, but the store faces the same open bay our boats cross running through the Ten Thousand Islands — the same water Smallwood’s canoe-borne customers paddled a century ago. Seeing that bay from a boat, the way every one of the store’s original customers did, is the fastest way to understand why this trading post ended up exactly where it did: not despite the water, but because of it. Pair a stop at the store with time on the water itself and the whole story clicks into place in a way a plaque on a wall never quite manages.

That’s really the throughline of this whole silo of stories. Places like the Smallwood Store, the shell mounds of Chokoloskee, and the backcountry channels beyond it aren’t roadside attractions — they’re water-only chapters of a coast that’s still mostly wild. Our captains grew up running these same passes, and a trip through the Ten Thousand Islands is as close as you’ll get to seeing this stretch of Florida the way Smallwood’s customers saw it.