On the net you can find many sites covering aspects of Daoism including its history. I don't intend to repeat what appears elsewhere and is written by far more informed people than me.
What I want to do here is provide a time line and sketch out a little detail of some particular highlights.
Late Neolithic: Prior to 2200 BCE, this period in history marks the establishment of agricultural settlements, the time before this period is considered by Daoists as an era of pristine existence. Prior to agriculture, humans lived in harmony with nature, a hunter gatherer lifestyle, governed by the seasons, the migration patterns of animals and the growth of wild plants.
Many of the perceived qualities of the people of this time (real or otherwise) are what Daoists seeks to regain.
This period is where some of the earliest aspects of Daoism such as Shamanism and Divination were established. Such activities were universal across all early developing civilisations and still persist in communities that have evaded mass industrialisation.
XIA: 2200 - 1766 BCE, this marks the establishment of early states in China, referred to as the Three Dynasties period.
Shang: 1766 - 1170 BCE, a period marked by the establishment of palaces and stately tombs for great leaders. It was also the period in which divination of a type related to the YiJIng is known to have existed, one such form of divination developed in this period was the writing on Scapula bones of simple formula, this at a later date became the foundation of the Yijing. Such divination methods may well have existed prior to this but no evidence survives to support such a hypothesis. Early theories of cosmology also date from this period laying the foundations for later schools of thought (Yin Yang naturalism) that evolved into Daoism.
Zhou: 1170 - 221 BCE, this period is of particular importance because it was the era of the Kings Wen and Wu and the Duke of Zhou. These people are credited with the creation of the early Yijing, developing it from earlier works in the Shang period, as we know it now and the yarrow stalk method of consultation.
The latter part of the Zhou Era was marked by the Warring States period. The few centuries of this period saw the 'flowering of one hundred schools' (100 in this context is not literal but rather implies very many). These school included: Kongfutzi (Confucius), Laozi (Lao Tsu) and Zhuanzi (Chuang Tsu).
Qin: 221 -207 BCE, this brief period marked the start of 2000 years of Imperial rule. It was started by Qin Shi Huangdi. He unified the area we now know as China and called himself "the first Emperor of China". This period probably saw the creation of the Wuxing (5 phases) school.
Han: 202 BCE - 220 CE, four hundred years of relative stability saw the forming of sate bureaucracy the adoption of Confucianism as the officially approved philosophy. It should be noted that Confucianism remained a key part of official state exams until the end of the Imperial period 2000 years later! It is this period that really cemented the Chinese identity.
Around 142 CE saw the establishment of the Celestial Masters school of Daoism. This was a large and successful group that actually established a regional state. It is also often referred to as the Five Pecks of Rice school. This was due to the fact that anyone joining had to donate Five Pecks of rice to the community. The group's influence faded by the fifth century.
Around 360 CE the Shangqing School was established, much of its theory was based upon spirit writing.
Tang: 618 - 907, often viewed as something of a golden era for Chinese culture. Art, poetry and the emergence of Buddhism and 'organised' Daoism all took place in this period.
Song: 960 - 1279, Neo Confucianism emerges as does early signs of foreign influence on Chinese culture.
This era also marked the foundation of one of the most influential of the later Daoist schools: Quanzhen Pai (The Complete Reality Sect). This school of Daoism believed that Daoist practice had become corrupted through misunderstanding of classic texts and lack of true transmission from teachers to students. This movement set about trying to remove some of what it believed was erroneous practice.
This school itself split into two differing approaches, they are identified by their geographical areas of influence, Northern and Southern. The Northern school was and still is, heavily influenced by Chan (Zen) Buddhism and is, in China, a largely Monastic movement.
The Southern School has more in common, though via different sources, with Tantric Buddhism. The Southern School was not monastic and featured a more eclectic approach to study with a traditional Master / Student relationship. Because of this approach (harder to control) the current Chinese state does not approve of or support it in the way it does the Northern Sect. As a result practitioners of the Southern methodology tend to be dispersed amongst the Chinese diaspora across Asia and now the rest of the world.
Another school that emerged at this time was the Zhenyi Dao school. This school established the selling of talisman as a means of making a living. It is a good example of "religious" Daoism. Its practitioners offered members of the public access to a number of deities for good luck and prosperity.
Manchu (Qing) 1644 - 1911, the last imperial dynasty ending with the republican period and occupation of much of China by Western powers and Japan.
Republic of China 1912 - 1949, China opens to western influence and the west becomes aware of aspects of Chinese culture.
People's Republic 1949, the arrival of state communism. Initial closing off to the west, massive turmoil and disruption. The 1970's saw a partial lifting of the "Bamboo Curtain" as Nixon initiates limited political and trade initiatives with China. This also opened the door to limited opportunities for western scholars to work and travel in China, bringing further knowledge of Chinese culture to the west.
At the same time as the west gained access to mainland China, British controlled Hong Kong saw the emergence of a film industry headlined by Bruce Lee. This raised awareness of Chinese martial arts in the minds of the masses and from this aspects of Chinese philosophy ceased to be a subject limited to scholars.
Interestingly, to me at least, this period also saw the creation of Traditional Chinese Medicine (TCM). TCM as it is known today is actually a modern creation. It was created by the Chinese Government in a desire to codify and modernise Original Chinese Medicine (OCM). The Government had initially tried to ban OCM and wanted China to adopt purely western medicine. This effort failed so in the spirit of 'if you can't beat them join them'. The Goverment took control of OCM grafted some western 'science' onto it and created TCM.
One thing that all modern followers of the Dao should clearly understand is that there is, and never was, a single form of Daoism. Even the brief history above should make it clear that Daoism has been subject to centuries of internal evolution and external influence and pressure. Many school ran concurrently with each other yet had a wide variety of beliefs and practises. One of the main things to be aware of, just as it is today, the most successful and well known is not by definition the best or most genuine. Much of Daoist history has been strongly influenced by how successful individuals and schools were at garnering state approval.