'Orlando' by Virginia Woolf

'The longest and most charming love letter in literature'

Photo by Yoav Hornung on Unsplash

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As many readers will be aware, June is officially Pride month, celebrating the LGBTQ+ community with vibrant Pride marches and other lively events.

The first official marking of Pride month came in June 1970, to mark the first anniversary of the violent police raid at New York’s Stonewall Inn on 28th June 1969.  

The Stonewall riots were a series of spontaneous demonstrations against a police raid which occurred in the early morning of 28th June.  The Inn was popular amongst the marginalised gay community as one of the few places they were welcomed, and police raids were routine throughout the 1960s.  

The police, armed with a warrant, entered the Stonewall Inn on 28th June without prior warning.  Violence broke out, thirteen people were arrested, including employees of the Inn and members of the community who were violating the state’s gender-appropriate clothing statute.  

Local patrons of the Inn who were sick of the constant police harassment and discrimination, as well as local residents, refused to disperse the scene on this occasion, becoming agitated at the aggressive handling of the community by the police.  This led to an outbreak of violence. 

The police, a few members of the community, and a writer for the Village Voice barricaded themselves into the bar, leading to an attempt to set the Inn on fire.  The fire department and riot squad were eventually able to put this out and rescue the citizens from inside the Inn, but the protests continued within the area for five more days, flaring up further when the Village Voice published an account of the riots.

Though the Stonewall uprising isn’t cited as the start of the gay rights movement, it did lead to more LGBTQ+ political activism.  Following the 1970 one-year anniversary march from the Stonewall Inn to Central Park, the first gay Pride parade was born, known at that time as the Christopher Street Liberation Day.  The official chant: “Say it loud, gay is proud,” heralded from this event.  

In 2016, President Barack Obama designated the Stonewall Inn as a national monument to recognise its contribution to gay rights in the US.

To kick off this pride month, I wanted to look at a book that has often been considered an early transgender novel for the way its protagonist changes gender within its pages.  That novel is Orlando by twentieth-century modernist Virginia Woolf.

Written in 1928, Orlando is a masterpiece of modernist queer fiction.  It chronicles the life of Orlando, who changes sex from male to female within the novel, spanning centuries and beginning in the Elizabethan era.  Woolf’s book is part-satire on English historiography.  

But it is also said to be a love letter to Vita Sackville-West, Woolf’s sometime partner, friend and muse. 

Vita Sackville-West, a writer in her own right, was also a keen garden designer and a fellow member of the infamous Bloomsbury Group of writers and artists, living and writing around Gordon Square in London’s Bloomsbury.  Vita and Virginia became lovers, a partnership lasting over ten years, despite both women being married. 

In true Bloomsbury fashion, gender boundaries and marriages did not stop love affairs from happening, and the bohemian way the members carried on their sexual relations had a clear effect on their art and writing at the time.  (Shout out at this point to the wonderful Victoria K Walker’s Publication, Beyond Bloomsbury, in which many of the writers and artists of this influential early twentieth-century group are celebrated).

It was Virginia and Vita’s relationship which inspired Woolf to write Orlando, which Vita’s son Nigel Nicolson later described as ‘the longest and most charming love letter in literature.’

Orlando by Virginia Woolf

As well as his mother, it was her family’s ancestral home of Knole House in Kent, with its lavish furnishings, family portraits, and many aspects of the original house which inspired the ancestral home of the novel.  

Vita, being female, suffered from the issue of primogeniture, meaning she was unable to inherit the home she loved, with it passing instead to the first male heir.  This was a deep sadness to Vita, who felt keenly the unfairness of being unable to inherit the home she loved due only to her gender.  Clearly, the idea of the gendered permutations of this struck a chord with Woolf, who’s imagination runs riot in this tale of a young man who eventually transitions into a woman, and feels the differences this brings to their experiences of the world throughout the centuries.  She allows Vita the resolution she longs for through her character of Orlando, who inherits her ancestral home, even as she transitions into a woman. 

Knole House, Kent

Although undoubtedly women of the upper- and upper-middle-classes within the early part of the twentieth-century benefited from lives of material comfort, they were also placed under intense social restrictions.  As Woolf had demonstrated in her treatise A Room of One’s Own, she believed in the importance of a woman’s ability to be financially independent in order to achieve her own liberty.  This was not an easy feat to achieve.  In Woolf and Sackville-West’s case, they were both married to respectable men, Virginia to the publisher and author Leonard Woolf and Vita to a diplomat and writer Harold Nicholson.  They both maintained open marriages, allowing them to feel free to pursue other relationships with both genders.  This was the way of the unconventional, bohemian Bloomsbury Group, though they often conducted their affairs within the constructs of conventional, respectable marriages.  

This combination of respectability and conventionality with the bohemian can be seen in some of the paintings at Sissinghurst Castle, the home which Vita shared with her husband, with some portraying Vita as the uptight Edwardian lady, and others, as a young, androgynous, youthful Vita living in her childhood home of Knole House.  

Vita Sackville-West by William Strang

The original manuscript of Orlando, with the inscription ‘Vita from Virginia’ resides at Knole House, which is now a National Trust property.

In 1992, the story was further mythologised in the film Orlando, directed by Sally Potter and starring Tilda Swinton.

The novel: an overview 

The story of Orlando spans over 300 years, between the years 1588-1928.  It features Orlando, who only ages by thirty-six years over this time frame, transitioning from male at the start of the novel to female.  

At the beginning, Orlando is a young noble, too young to fight but enjoying pretending to chop off the heads of Moors as his father and grandfather before him.  He longs to have adventures and travel the world.  He enters the woods to write poetry and falls asleep, being awakened by trumpets sounding the arrival of Queen Elizabeth.   

Impressed by the young Orlando, the queen sends for him two years later, to attend her court, making him her Steward, Treasurer, and lover, with all the wealth and status he could ever hope for.  

Orlando enjoys mixing with the lower-born citizens and frequenting local pubs to frolic with young women, however when he tires of this, he returns to court, now under the reign of King James I.  Many relationships and even an engagement ensues, then Orlando falls in love with a Russian Princess, only to devastatingly lose her.  He therefore locks himself away to become a writer. He invites a famous poet to stay with him by the name of Nick Greene, who eventually leaves and writes a parody of Orlando.

The novel moves on through the reigns of Charles II, who sends him as an ambassador to Constantinople, being subsequently made a Duke.  Following a brief marriage to a Spanish dancer, and an insurrection in Turkey, Orlando falls into a trance, waking after seven days as a woman.

This turn of events, though perhaps startling to the reader, does not appear to surprise Orlando, who quickly accepts her new body.  

She returns to England, becoming romantically involved with the ship’s Captain, and puzzles over whether she enjoys being a man or a woman more.  

She begins spending time with famous poets of the era, as well as some London prostitutes.  Whilst in London, Orlando looks up at the darkening sky and realises that the long Eighteenth century is closing and the nineteenth has begun.  She feels the gloominess of the Victorian era and the pressure to find a suitable husband.  She meets and marries a man who appears to have all the good qualities of a woman, as he revels in the fact that Orlando has all the good qualities of a man.  

She eventually finishes an important poem she has been working on throughout the novel, ‘The Oak Tree’, and meets up with her old nemesis Nick Greene, now an eminent literary critic.

She lives through King Edward VII succeeding Queen Victoria on the throne and witnesses the world becoming much brighter, though also more desperate.  

She gets struck ten times on the head as the clock strikes 10am on Thursday 11th October 1928; she is now in the present day, aged thirty-six. 

Orlando now has the realisation that everything is connected, and thinks about all the different selves that compose her.  In wishing to know who the ‘real’ Orlando is, she realises that she is all of them.  But she is also frightened by the present, and looks at her huge ancestral home, thinking how it no longer just belongs to her but also to history.  She hears an air plane in the skies above, and the clock strikes midnight: it is the present day.  

So: wow!  If you’re thinking that must be a heck of a long novel: it isn’t.  All the action of this story takes place in just 192 pages of Virginia Woolf’s hypnotic, fantastical prose.  And I have just given a condensed overview here!  There are many characters and historical details within the text, which reveals itself as an exploration of British history, the changing monarchy, oncoming technology and the present day, as it was in Woolf’s time.  

When I first encountered the book as an undergraduate, I couldn’t quite make it out.  It moves so swiftly between eras and historical events, and even gender of the protagonist, without any kind of preamble or warning.  It sounds fantastical, but in the reading of the book, it just kind of…works.

I can’t possibly represent the book fully within this short essay.  It is a novel which requires reading to be understood, and there are many critical resources out there which explore and examine the themes and concepts more fully.

But I just wanted to bring it to the attention of readers who might have read the perhaps more ‘popular’ novels of Virginia Woolf, such as Mrs Dalloway and To the Lighthouse.  This book was a revelation when I first encountered it, and it feels like one that will yield something new on every return.

It also felt relevant to this month of Pride, and in the understanding often lacking in narratives around the gender binaries. 

In Woolf’s novel, sometimes tongue-in-cheek, and with a nod to the absurd, she explores what it means to be truly androgynous; of all the different selves that compose us as human beings; and of the interconnectedness of us all.  

I just wanted to give another quick shout-out to this new newsletter, Qstack, comprising The LGBTQ+ Directory of Substacks. 

Hungry for more Pride related essays?  You might enjoy my earlier essay on the LGBTQ+ writer Rita Mae Brown and her seminal text, The Rubyfruit Jungle, as well as this one on Patricia Highsmith’s Carol (also known as The Price of Salt).

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