The eponymous hero is born as a male nobleman in England during the reign of Elizabeth I. He undergoes a mysterious change of sex at the age of about 30 and lives on for more than 300 years into modern times without ageing perceptibly.
As a teenage boy, the handsome Orlando serves as a page at the Elizabethan court and becomes favorite of the elderly queen. After her death he falls deeply in love with Sasha, an elusive and somewhat feral princess in the entourage of the Russian embassy. This episode, of love and ice skating against the background of the celebrated Frost Fair held on the frozen Thames River during the Great Frost of 1608, when birds froze in mid air and fell like stones to the ground, inspired some of Virginia Woolf's most bravura writing:
Great statesmen, in their beards and ruffs, despatched affairs of state under the crimson awning of the Royal Pagoda ... Frozen roses fell in showers when the Queen and her ladies walked abroad ... Near London Bridge, where the river had frozen to a depth of some twenty fathoms, a wrecked wherry boat was plainly visible, lying on the bed of the river where it had sunk last autumn, overladen with apples. The old bumboat woman, who was carrying her fruit to market on the Surrey side, sat there in her plaids and farthingales with her lap full of apples, for all the world as if she were about to serve a customer, though a certain blueness about the lips hinted the truth.
