Bagwell was a passenger on the Sea Venture, which foundered on Bermuda after being caught up in a hurricane on the way from London to Virginia in 1610. The survivors built two pinnaces from the wreckage of the Sea Venture and native cedar that was abundant on Bermuda. The Deliverance and Patience brought the passengers and crew to Virginia, where they arrived in April 1611. Henry Bagwell was aboard the Deliverance.

In 1622, he was living at the West & Shirley Hundred plantation in Charles City, and he survived the 1622 Indian massacre.

By 1632, he had settled on the Eastern Shore and became the first clerk of the court for Accomack County.

He served in the House of Burgesses in 1630 and 1632.