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Chokoloskee Island as seen from abovePhoto: Spaluch1 · CC BY-SA 4.0
–Not graded
History · Chokoloskee

Chokoloskee’s post office opened in 1892, and 1 of its places is on the National Register

Most of Chokoloskee was built recently: 0.0% of its homes predate 1940 and the median home dates from 1991. Its Register listing is the Ted Smallwood Store. Below: 2 old photos and papers, maps from 1974 on, and the census since 2000.

1892first post office
1on the National Register
0.0%homes built before 1940
2old photos & papers
Add an old photoShare a memory
From Chokoloskee’s archive · credits on each photo
Quick answers

How Chokoloskee began

When was Chokoloskee founded?

1892

The Chokoloskee post office opened in 1892, the earliest record of the town by name.

First census: 404 in 20002020 census: 346134 years
Founding year: the first Chokoloskee post office (Blevins & Helbock, CC0).The full story ↓

What stands out about Chokoloskee’s past

Read from the archive, the National Register and the record. The page puts what stands out first.

A history waiting to be writtenOnly 2 old photos are in the public archives. The rest are in attics and albums.
★ What stands out · Help out

Start Chokoloskee’s collection

The first neighbors to add old photos shape how Chokoloskee’s history is told.

Decades since 1900 with photos
00s10s20s30s40s50s60s70s80s90s
2 of 10 decades. The empty ones are waiting for someone’s album.
Retake an old viewSeminole chickee on Chokoloskee Island,…: stand where they stood+15Share a family photoSign in to add one+10
The story

How Chokoloskee came to be

From Wikipedia’s history of Chokoloskee.

Read it all →

Chokoloskee Island was inhabited by the indigenous Calusa and their ancestors for more than 1,500 years before European explorers reached the area. By the time Spain transferred Florida to Great Britain in 1763, the area was uninhabited. During the first three-quarters of the 19th century, Chokoloskee Island may have been occasionally visited by Seminoles, white hunters, "Spanish Indian" fishermen from Cuba and various "refugees from justice".

ChaptersBefore European settlementEarly settlementTed SmallwoodEdgar WatsonOperation EvergladesEducation, religion and medical care

Text from Wikipedia, licensed CC BY-SA 4.0.

Timeline

Chokoloskee, 1892 to 1974

Woven from the archive, old maps, post office records, the National Register and the people born here.

  1. 19th century
  2. 1892Post officeThe Chokoloskee post office opens
  3. 20th century
  4. 1916In the archiveSeminole chickee on Chokoloskee Island, Florida
  5. 1917BuiltTed Smallwood Store is built
  6. 1967In the archiveErnest Hamilton's stone crab store - Chokoloskee Island
  7. 1974On the mapFirst mapped by the U.S. Geological Survey
By decade

Chokoloskee, decade by decade

2 decades in the archive, from the 1910s to the 1960s. Scroll each row; tap a photo for its story.

1910s1 item
Seminole chickee on Chokoloskee Island, Florida1916Seminole chickee on Chokoloskee Island, Florida
1920s–1950snothing yet
Nothing in the archives for these yearsWeddings on Main Street, storms, parades, school pictures, the old store. If it’s in your family album, it belongs here.
Add from your album
1960s1 item
Ernest Hamilton's stone crab store - Chokoloskee Islandc. 1967Ernest Hamilton's stone crab store - Chokoloskee Isla…
1970s–1990snothing yet
Nothing in the archives for these yearsWeddings on Main Street, storms, parades, school pictures, the old store. If it’s in your family album, it belongs here.
Add from your album
Today11 recent
Chokoloskee Island as seen from above2021Chokoloskee Island as seen from aboveChokoloskee, Florida2019Chokoloskee, FloridaBrown pelicans2015Brown pelicansChokoloskee, FL 34138, USA2014Chokoloskee, FL 34138, USAChokoloskee, FL 34138, USA - panoramio (4)2014Chokoloskee, FL 34138, USA - panoramio (4)Chokoloskee, FL 34138, USA - panoramio (3)2014Chokoloskee, FL 34138, USA - panoramio (3)Chokoloskee, FL 34138, USA - panoramio (2)2014Chokoloskee, FL 34138, USA - panoramio (2)Chokoloskee, FL 34138, USA - panoramio (1)2014Chokoloskee, FL 34138, USA - panoramio (1)Chokoloskee FL south022010Chokoloskee FL south02Chokoloskee FL south012010Chokoloskee FL south01FLMap-doton-Chokoloskee2004FLMap-doton-Chokoloskee
On the map

Chokoloskee on the map in 1974

The U.S. Geological Survey’s map of Chokoloskee.

Chokoloskee on the 1974 USGS map1974Chokoloskee sheet · 1:24,000

U.S. Geological Survey historical topographic maps (public domain), via Esri’s collection of the scans. The red ring marks the center of Chokoloskee.

Then & now

Stand where they stood

No then-and-now pairs yet. Take a photo from the same spot as an old one and they appear here side by side.

Seminole chickee on Chokoloskee Island, Florida
Retake this viewSeminole chickee on Chokoloskee Island, Florida, 1916

Find the spot, match the angle, and add your photo. It becomes the first then-and-now pair on Chokoloskee’s page.

Retake this view · +15
On the National Register

1 historic place in Chokoloskee

The country’s official list of buildings and places worth saving.

place listed
1
National Historic Landmarks
0
none yet
historic buildings protected
1
each building in a district counts
first listed
1974
Ted Smallwood Store
Ted Smallwood Store, built 1917
Buildings
Ted Smallwood StoreBuilt 1917

National Park Service, National Register of Historic Places. Photos from Wikimedia Commons, credited on each place’s page.

People over time

Chokoloskee, census by census

010020030040020002020Peak: 404

Between 346 and 404 people in every census since 2000.

3 censuses, 2000–2020.

U.S. Census Bureau decennial counts, from the census table on Chokoloskee’s Wikipedia page.

Famous people

Famous people close to Chokoloskee

Nobody well known was born in Chokoloskee itself, so here are the best known from just nearby.

See all →
Bruce J. ScottAmerican politician · b. 1933
Neal StorterAmerican football player · b. 1890
M
Mark CalviCollege baseball coach · b. 1969

Questions about Chokoloskee’s history

What year was Chokoloskee founded?

The Chokoloskee post office opened in 1892, the earliest record of the town by name (U.S. post office records).

What is on the National Register in Chokoloskee?

One place: the Ted Smallwood Store (listed 1974).

Memory lane

What the archives can’t tell you, neighbors can.

Town Square →
Start a conversation
Sources

Where this page comes from

Founding dates: Wikidata, Wikipedia, the U.S. post office records of Blevins & Helbock (CC0) and the Census. Homes by year built: Census ACS 2020–24. National Register of Historic Places: National Park Service (list of May 22, 2026). Old photos, postcards and papers: Wikimedia Commons, the Library of Congress and other public archives, credited on each item’s page. Maps: U.S. Geological Survey historical topographic maps (via Esri) and Sanborn fire-insurance maps (Library of Congress). History text and census tables: Wikipedia (CC BY-SA 4.0). Places that used to be: USGS Geographic Names Information System (2021). How TownRatings grades history →

From Wikimedia Commons (13), Wikidata (1), the National Register of Historic Places (1), Wikipedia, U.S. Geological Survey historical maps, U.S. Census counts (via Wikipedia), the US Post Offices dataset (Blevins & Helbock) and the USGS Geographic Names Information System. Archive images are copied here with their credits and licenses, shown on each photo’s page. Refreshed monthly.