Robert started writing poetry from a young age and found support in the local bardic community, gaining the friendship of Thomas Thompson (1773-1816), who was considered to be one of the finest and earliest Newcastle poets. Gilchrist was held in high regard. In 1818, at the age of 21, he received a silver medal from his companions in appreciation of his poetry. His special place amongst the community was recorded in the song ‘Thumping Luck to Yon Town’, by William Watson, a painter and politician, who was writing poetry and songs between 1820 and 1840. Watson notes Gilchrist’s “comic song” amidst the wit and humour of notable others such as Thompson and William Mitford. Gilchrist's poems were published alongside these poets in group anthologies that dealt with common local or regional themes.

Gilchrist was patroned by the Mitchell family, an influential publishing family from Newcastle who published the Tyne Mercury newspaper, for whom Gilchrist wrote occasional verse. His leading patron, W.A. Mitchell, was particularly inclined to support poets from humble origins. Mitchell’s philosophy is displayed in an essay he wrote in 1817, An Essay on Capacity and Genius. Inspired by the educational philosophies of John Locke, which aimed to break down the barriers between the literate and illiterate, Mitchell thought there was no such thing as innate genius; man’s mind was a blank slate to be shaped by beneficial social conditions, education and the guiding hand of encouragement by patrons. In W.A. Mitchell Gilchrist had found a keen sympathiser. His poetic ability was also fostered by the local bardic community, which was considered by one commentator to be so strong that poets "flourished as common and prickly as brambles along the banks of the Tyne.” Local poet Charles Purvis celebrated this community in his 1812 verse 'Bards of the Tyne':

Ye sons of Parnassus, whose brains are inspir’d
With envy or madness, dame dullness, or wine,
Who wish to be flatter’d, or prais’d, or admir’d,
Leave thinking, and fly to the banks of the Tyne:
No wit is requir’d
To make you admir’d,
Let doggrel run limping thro’ each crippled line;
No humour degrades,
Nor genius pervades
The verses sublime of our Bards of the Tyne.

Gilchrist's first book-length poem Gothalbert and Hisanna was published in 1822. In 1824 his Collection of Original Songs, Local and Sentimental was published by W.A. Mitchell. The second part appeared in 1826 (his last book length publication) published by W. Boag.

Gothalbert and Hisanna was semi-autobiographical and within it are clues to Robert’s humble origins. Early lines show his father to be a modest and parochial figure: "He knew no luxuries, ever bluntly spoke, And seldom rov’d beyond his chimney smoke.” Whilst Robert would later take over his father's sailmaking business, he is keen to distance himself from his labouring identity. No poem deals with the production process or business aspects of sailmaking, neither is there evidence in his writings that he sought the sobriquet 'The sailmaker poet'. The prologue to Gothalbert and Hisanna acknowledges his writing was “the offspring of a few leisure hours.” And later in the titular poem he writes that bards favour “ease, good wines and custard – And hate hard work as much as cats do mustard.” This was typical of labouring-class poets throughout the eighteenth and nineteenth centuries, a form of reassurance that poetry was composed to relieve drudgery and to reassure aristocratic and bourgeois readers of the importance of their trade; that poetry might be idle but their real work carried on regardless.

Nevertheless, the literary merits and pretentions of Gilchrist were criticised in Gothalbert of the Tyne, a book published by the Sunderland poet T. Ferguson, written in response to Gothalbert and Hisanna. Ferguson's ire was directed towards the effects of education upon the lower classes. Ferguson wrote a series of explicit attacks to demonstrate the danger posed to literary standards by labouring-class writers such as Gilchrist. He noted that whilst publications like Gothalbert and Hisanna are largely ephemeral and parochial, he feared the populism of such efforts – especially for men of “taste and impartiality” who have a moral and immediate cause to defend literary standards and values. Ferguson questioned the pretentions of labouring-class poets whose “hands profane” and pollute the sacred Mount Parnassus, home of the muses. Through a series of three similes – the Fable of the Bear; Aesop’s fable of the donkey and the lion; and an industrial simile of the poet as machine - Ferguson erects a barrier to entry, which ridicules and mocks the efforts of Gilchrist. Quite why Gilchrist and his early literary efforts should rile Ferguson in particular is unknown. However through the attack, maintained throughout 26 pages, Gilchrist is revealed to be an immature, derivative and ill-disciplined poet in desperate need of finer craft skills than to rely on his limited 'natural ability'. Despite this, Gilchrist maintained a production of verse throughout the 1820s and 1830s, many of which were republished in local anthologies in his own lifetime and beyond, including Fordyce's 1842 Newcastle Song Book, Joseph Robson's 1849 Songs of the Bards of the Tyne, and Thomas Allan's 1862 Tyneside Songs and Readings.

Upon the death of his father, John Gilchrist, in 1829, Robert took over his father's business near the Custom House on the Quayside. He was not successful in the business preferring the country and long walking tours. Gilchrist resided in the old house facing Shieldfield Green, reputed to have housed King Charles during the English Civil War as a prisoner of the Parliamentarians. In 1838 he wrote a poem 'The humble petition of the old house in the Shield Field' to Mr John Clayton Esq. complaining of plans which threatened to destroy this house. The house was spared. A memorial plaque stands on Shieldfield Green to commemorate the famous inhabitants of the house, which eventally succumbed to urbanisation and redevelopment in the 1960s.

Gilchrist had some involvement in local politics and must have had a degree of status in Tyneside. He was a freeman, a member of the Herbage Committee, which tended Newcastle's Town Moors, and took part in the annual Barge Day event, a local custom in which the Mayor and barges representing the Town's Guilds sailed the length of the Town Corporation's boundaries on the Tyne. Following the Poor Law Reforms of 1834 and the creation of the Newcastle-upon-Tyne Poor Law Union in September 1836, Gilchrist was elected to the Board of Guardians, representing the All Saint's Parish. This role would have meant him adjudicating between deserving and undeserving poor, deciding on the fate of unfortunate individuals and families as they entered the newly constructed Newcastle Workhouse.

Robert died on 11 July 1844 at the Old House in Shieldfield, aged 47, and was buried at the East Ballast Hills burial ground. The cause of death is given as a chronic stomach ailment, possibly cancer. John Luke Clennell, the son of the engraver and poet Luke Clennell (1781-1840), paid tribute to his old friend in the poem below, dated 16 July 1844:

If honest, manly, unpretending worth
May justly claim from us a tribute dear,
And those who were respected whilst on earth,
Deserve a passing dirge sung o’er their bier,
Then may I write me ROBERT GILCHRIST here.
No vain and empty words are these to tell
A tale of sorrow in an idle rhyme;
I knew the simple-hearted fellow well,
And felt his kindness also many a time.
Thus it is fitting memory should dwell
In pensive sadness on a man who gave
Good cause for us to sorrow o’er his grave,
And that the Muse bear record with a sigh,
When now it is the poet’s lot to die.

Robert left behind a wife, Margaret Bradley Morrison, whom he married in 1826, and five remaining children, many of whom carried on in sailmaking and maritime trades. The family relocated to East London (West Ham) in the mid-1850s - one can speculate that they were victims of the Great Fire of Newcastle and Gateshead which destroyed a substantial amount of quayside property on 6 October 1854.

Unlike later Tyneside poets such as Ned Corvan, Gilchrist has received little attention. There are good scholarly reasons for the lack of posthumous fame or critical inquiry into his works. Many of his poems display a rustic naivety, a charge made by Lord Byron in English Bards and Scotch Reviewers of local poets of the Georgian era. This rustic naivety, as subject theme and quality, does not lend itself as easily to studies of the north-east and its popular cultures, where other poets and songsters have been studied for their contribution to music hall culture, to sports culture, or for popular songs that became a strong part of the regional identity. The physical cultures of the North East, of the pit and heavy industry, overtake those of the town's maritime and mercantile culture and its people. Furthermore, Robert Gilchrist's output appears to diminish in the 1830s, with one biographer writing that he downed his pen upon the death of Blind Willie, a celebrated Quayside eccentric, out of respect. This is unfortunate as it places Gilchrist in a pre-Chartist literary and political landscape; his poetry is neglected as it does little to inform on the development of a political consciousness in the formative years before the Chartist movement.