Pigeon Key is popular because of Henry Flagler and his East Coast Railroad Extension. Flagler was responsible for bringing railroad to the Florida Keys and much of the Everglades area as well, in the first half of the 20th century. The volunteer group named the Pigeon Key Foundation is responsible for preserving this piece of Florida Keys history and making it accessible to visitors.

Flagler's railroad used Pigeon Key as a construction base site for his railroad project from 1908 to 1935, and the road which was built to the Key for this purpose is still used today. Although you can't drive your car on the road/bridge to Pigeon Key, it is used by a trolley which takes visitors to Pigeon Key on the hour every hour between 10am and 4pm. The terrifying 1935 hurricane that wiped out much of the middle Keys destroyed Flagler's railroad, and he decided not rebuild after the devestation. A few years after the hurricane, the first Seven Mile Bridge was built alongside Pigeon Key, right over the old railroad spans. Pigeon Key took on new life as the Bridge & Toll District headquarters. When the new Seven Mile bridge was built in the early 1980's, Pideon Key was no longer part of the pathway for cars, but part of the old road was preserved for the trolley car and for joggers and walkers. It makes an excellent workout, at 2 miles to the island, four miles round trip. You can look down and see sting rays in the water sometimes.

Pigeon Key had several other jobs over the years, including a U.S. Navy site, a fishing camp, a park, and a marine biology center for the U. of Miami. Now it's a carefully preserved piece of Florida Keys history. Look for the Pigeon Key Visitors Center at MM 47 on the oceanside on Knight's Key. Here, the trolley sits on the old tracks, waiting to take visitors over to Pigeon Key. The driver will tell you about the history on a 20-minute tour of the island, and you can stay on the island as long as you like, until the last trolley at 5pm if you like. There's a small fee for the tour, even if you walk to the island.