Cooktown was settled by Captain Cook in 1770 when the Endeavour boat was beached here, and is where Joseph Banks gathered 186 different species of Australian plantlife along the Endeavour River. Cooktown grew to the second largest town in Queensland after the Palmer River Gold Rush, although WWII and various cyclones almost destroyed Cooktown.

Webber Esplanade is to the north of the town and starts at the tip of Grassy Peak, where you will find the Powder Magazine which is the oldest brick building in Far North Queensland. There is a great view from the headland as well as from the top of the hill and it makes a pleasant walk back towards town, along the Endeavour River. Once in town, the road turns into Charlotte Street and is where you will find a bank, some cafes and restaurants, many shops, a post office and several pubs. There are also some memorials and monuments along Charlotte Street, for Captain Cook and other explorers.