The first humans to reach Virginia arrived when sea levels were much lower, perhaps 10,000 years before the Chesapeake Bay developed. The first Virginians may have walked into the boundaries of the modern state from the north, west, or south.

We don't know for certain how Virginia was first settled. However, we know that global warming and global cooling have caused the shape of the continents to vary, as the continental shelves have been exposed or flooded.
The Atlantic Continental Shelf (the physiographic province east of the Coastal Plain) was exposed when the Bering Strait was also dry land. The land of Virginia extended much further to the east when the glaciers and ice caps "pulled" water from the oceans. During the warmer climate stages when the ice melted, both the Atlantic Continental Shelf and the eastern edge of the Coastal Plain of Virginia were flooded.
At the moment, sea levels are rising and the Coastal Plain is being inundated again. Barrier islands are migrating westward. If that pattern continues over the next few centuries, Tangier Island will be completely inundated and low-lying cities such as Norfolk will have to build massive flood walls.
If the Greenland ice sheet or the Antarctic ice sheets melt, then sea level could rise another 20-50 feet higher - forcing residents on the Atlantic coastline to abandon their "turf" and migrate inland, just as the first Native Americans in Virginia did as the river valleys flooded and the Chesapeake Bay formed.

Right now, the shelf between Russia and Alaska is covered with water, called the Bering Strait. During the Ice Ages, however, sea level was hundreds of feet lower because so much water was trapped in glaciers, and there was a land bridge connecting the continents. The general consensus is that Asians crossed to North America and the genetic stock that settled Virginia originally was derived from the hunting groups that moved across that land bridge.
One theory suggests some Asian hunters reached the West Coast in boats or rafts. We know the islands in the Pacific (including Hawaii) were settled by people who drifted to them on rafts - or used some navigational technology to direct their journey by sailing or paddling. And it may be true that Vikings arrived in North America before Columbus... but by the time the Vikings got here, they found the continent already settled by prior immigrants.
However and whenever they arrived, the Native Americans in Virginia were a low-tech culture compared to modern-day Virginians. In 1607 the Virginians had no airplanes, no Metrorail or Virginia Railroad Express, no Omnilink or Fairfax Connector bus, no cars. The Native Virginians who greeted the Jamestown settlers (or the Spanish who arrived 37 years earlier...) did not even use the wheel - and they did not have horses.
To get around for about 10,000 years, the Native Americans in Virginia walked or canoed. The Native Americans had no sailing ships, but they were using canoes routinely when the Europeans like John Cabot sailed along the North American shoreline at the end of the 15th Century.
By 1607, Powhatan's power extended across the Chesapeake Bay to the tribes on the Eastern Shore. Powhatan did not fully control the tribes north of Potomac Creek, on the northern tip of the Chesapeake Bay, or on the northern part of the Delmarva Peninsula. It's safe to assume Powhatan's emissaries did not walk from Werowocomoco to the Eastern Shore by going north around the tip of the Chesapeake Bay, through territory controlled by other tribes - instead, they used canoes to cross the bay. We haved the historical records of the English colonists to confirm the Algonquians used canoes.
The Virginia Indians also used stone tools, including "points" and scrapers with sharp edges that could be used to cut tree trunks to a desired length. Cutting a large standing tree with just stone tools would have been possible, and would have allowed the Indians to select the most desirable tree trunks - but the investment in labor would have been immense. Instead, they used fire.
On occasion, floods brought a supply of trees to the boatmakers, eliminating the hard work of cutting big trees with fire and stone/bone tools. The Native Americans may have selected the best trunks from the intermittent flood logjams, and then converted those trunks into canoes. After all, the flood-provided trees were already cut and on the shoreline - would you go into the forest, select a tree, cut it down, and drag it to the river if there was a canoe-in-the-making already floating on the water?
The Native Americans used fire together with stone tools to excavate the excess wood and shape the tree trunk into a canoe. That would have required skill as well as patience. Making a canoe in Virginia before the Spanish, French, Dutch, and English arrived would have required a month or more of work. Those boats were manufactured with Stone Age tools, until the Europeans arrived and brought iron and steel. The Powhatans made canoes from trees, burning and scraping away the charred wood with sharp stones or shells until the trunk had been hollowed out.


Coals would be placed on the section of tree to be removed, charring the wood and making it easier to scrape away. But how did the canoe makers avoid burning sections of tree trunk that were not to be removed? Mud, good ol' Virginia mud. Mud was plastered on the edges of the trunk, ensuring that only the sections intended to be removed would burn. A thick layer would be slathered carefully on the edge of the tree trunk, and it would stop the fire from weakening the portion of wood that was being retained.