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Though many of the old families of Somerset survived the devastating Wars of the Roses and managed to hold onto their lands, the accession of King Henry Tudor to the throne of England, and later the dissolution of the monasteries, brought opportunities for many 'new men' in the county. The Pophams, a family of lawyers who became Lords Chief Justice; the Wyndhams of Orchard Wyndham, the Phelips of Montacute, Sir Edward Rogers, Sir Ralph Hopton and others. New or old, they served the crown in many matters of National import. Sir Amias Poulett, of that ancient family of Hinton St. George, for instance, was one of those chosen to escort Princess Catherine of Aragon through the county, upon her arrival at Crewkerne from Plymouth. Successive descendants were Governors of Jersey and a younger Sir Amias was appointed keeper of Mary, Queen of Scots. He became a strong supporter of her execution.

Ordinary Somerset men followed their lords in such events. Soldiers from Dunster were almost certainly present with Sir John Luttrell at Boulogne in 1544 and, three years later, at the Battle of Pinkie against the Scots. Naval contingents from Somerset were also abroad. Thomas Wyndham took a squadron of three ships to Morocco in 1552 under Master John Kerry of Minehead; and John Leach took The Emanuel from Bridgwater on Frobisher's third Voyage, in 1578, in search of the North-West passage to India. In later years, Somerset settlers in the Americas, included Sir Ferdinando Gorges of Wraxall who founded New Plymouth (1628) and became Lord Proprietary of Maine; Nicholas Dodge of East Coker who established a settlement at Block Island; Richard Tucker of Stogumber and George Cleaves of Brompton Ralph founded Stogumber in New Somersetshire and Falmouth in Maine; and Richard Treat of Pitminster who was one of Charles II's patentees for Connecticut.

By the 16th century, when the geographer John Speed visited the county, Somerset was a place of great diversity. Speed noted pasture for livestock, birds and fish in the recently drained wetlands near Glastonbury and valuable lead and other mineral deposits in the Mendip Hills. Local coal was used for smelting iron and lead and the quarries at Ham produced quality building stone. The following century, however, brought turmoil to this idyllic rural scene. The Civil War between King Charles I and his Parliament, tore the the inhabitants of Somerset in two. The Somerset gentry, and most of the rural population, were Royalists, even though they disliked some of Charles' policies, while support for Parliament was represented by the puritans, particularly in the towns, in the north of the county. When Parliament tried to take control of the local militia, the two sides swiftly divided and the first armed skirmish in Somerset was a victory for the Royalists at Marshall's Elm (near Street) in the late summer of 1642. Despite this encouraging start, the county was dominated by Parliament throughout 1643. Fortunes changed the following year, though, when the Royalists regained the upper hand under the command of Sir Ralph Hopton. He besieged Taunton, Bridewater and Dunster and finally drove the Parliamentarians from Somerset at the bloody Battle of Lansdown.. Their victory was not conclusive, however, and the Royalist defeat at the Battle of Langport in 1645 heralded the beginning of the end for their cause in the county.