Benjamin Boyd needed to create a link between his property at Twofold Bay and his 14 leased stations on Monaro on which he grazed sheep and cattle. Overland from Sydney, these leases were 300 miles distant, but only about 80 miles from Eden.
In 1843 Boyd and his friend Oswald Brierly left Boydtown and followed a route through the present villages of Towamba, Burragate and Rocky Hall as far as the mountain which they ascended via the Cowbail Track to Maffra Station held by Boyd. On the return journey they turned off at the home of William Hibburd, later known as the St George and Dragon Inn. At the time, Hibburd leased Archer's Flat and Bibbenluke Stations. Descending the mountain via Tantawanglo they reached Peter Imlay's home at Candelo. Brierly wrote in his diary:
"Here we got a capital breakfast consisting of potatoes and meat and had a refreshing wash in the delightful river that ran past the house. About 2 in the afternoon we reached Candelo and were received politely by Peter Imlay. There was a good garden of strawberries. After a pleasant conversation of schoolboy recollections, a pouch of tobacco and a few songs we took our leave and pushed on, intending to reach Pampoola."
(Southern Record and Advertiser 13.11.31)

The route became known as Boyd's Road and was the only one known to be followed to Monaro until Merimbula was opened as a port in 1855. George Grant in his memoirs tells how in that year his family left Merimbula and taking a route via the Peak and Honeysuckle, joined Boyd's Road near the present New
Buildings bridge, at which place Boyd had built an inn. Grant wrote:
"On to the Towamba River in which we found a good fresh running. We could see the Boyd inn on the other side. We had to camp there for two days until it went down. There were lots of folk coming through. Some riding horseback, some walking leading horses and spring carts. Lots walking and carrying big swags. Next morning the place looked like a circus starting up."

The ascent of the mountain then most commonly used was by the Coal Hole or Bridle track, although another track, the Purgatory, was later preferred by the teamsters because of its easier grades. All these tracks converged on Hibburd's Inn which was licensed in 1844 near the present Cathcart.

Hibburd was granted his license following references from persons of high standing, including John Macarthur, who described him as "honest and industrious". He also had the support of the Colonial Secretary, Alexander McLeay, who leased McLeay's flat near the Yellow Waterhole.
The Coal Hole track was to become the Big Jack road in 1868 and follows the source of the Towamba River. As Hibburd's leases extended down the mountain to join the Walker's leases in 1848, he built another inn. the 'Roan Horse' at Pambula. His idea was to develop another route to meet up with Boyd's road near Rocky Hall at Boyd's inn and as an early step, he lobbied for the election of Daniel Egan as the first to represent the electorate of Manaroo, later Eden, in the N.S.W parliament. Using this political influence and the support of the Monaro squatters, Hibburd pursued his idea of a new road by building another inn at Honeysuckle which was licensed in 1855. George Grant described the inn:
"The Honeysuckle inn was conducted by an old French woman who sucked a clay pipe and supplied lodgers with overproof rum and turned on some wild parties playing up considerably and doing an Irish jig."
He may have been referring to Mary, the wife of the licensee William Thompson, but the description better fits that of Ann Love, the wife of a later licensee. Both ladies were thrice married and each was long remembered for her exuberant behaviour.

The discovery of gold at Kiandra in 1860 brought a flood of diggers into Merimbula port and led to the erection of several more inns, including McCauslands at Lochiel, Turbets and Loves at Wyndham and Hibburds at Rocky Hall. Two newspapers started in Eden giving local news formerly given by the Illawarra Mercury. Neither paper lasted more than a year but the Bega Gazette started in 1864.

The gold discoveries brought the need to station police along the route after a number of disturbances. Mrs. Love at the Old Stockyard inn was stuck up by men who "threatened a hot seat on the fire if she did not give them what they desired."
Monaro was infested with sly grog shops, robbers and murderers. The Clarke bushrangers killed several people, including the policeman Miles O'Grady at Nerrigundah. The Clarke brothers were hanged in 1868. The safe way to the diggings was by steamer, the newly formed Illawarra and South Coast Steam Navigation Co. having been recently formed, serving the ports of Eden, Merimbula, Tathra and Bermagui, the latter continuing to serve the Cobargo area until the Company ceased operating to all ports in 1955.

With the advent of local newspapers travellers commented on the scenes and events along the way. The Twofold Bay and Maneroo Observer of 1860 has accounts of the mountains - their "dark frowning terrible heights almost touch heaven causing a thrill in this great valley, frowning in awful majesty"... "sun's rays playing with feeble effect."... the "Towamba River creeps as if by stealth along the bottom of this mighty chamber in the earth's surface" But at the top, the scene is impossible to describe where, "the foliage assumed a more beautiful aspect and thousands of birds dance on every bough".

Another traveller comments on the Honeysuckle Inn:
"The Honeysuckle is an old established roadside house and being situated in an open flat valley with its high post on the opposite side of the way, the sign board suspended and swinging in the breeze it forcibly reminded me of the picture of an English roadside inn in the olden time. A large party of diggers en route for the Snowy were playing quoits in the large open ground behind the hotel as I passed through this village."
(T. Bay & Maneroo Observer 17.8.1860)

After 1861 with the Free Selection Act. small farms replaced the large holdings creating villages and a permanent population. A road closer to the port of Tathra was needed, so another was built via Tantawanglo, by-passing Rocky Hall, although teamsters preferred to use the purgatory track east of the Coal Hole near Rocky Hall, and maintained Eden and Merimbula as their preferred ports. It was not until 1901 that Merimbula had a deep water port, when a wharf was built outside the lake entrance.

The coastal steamers continued until the train line from Queanbeyan moved south, which in time led to the construction of the Brown Mountain road. Pat Farrell, a teamster himself, recalled that his father David, carried big loads of wool from Corrowong station near Delegate to Merimbula down the Big Jack road and back-loaded cargo from ships until his death by accident. when he was crushed by a wagon in 1927. At that time, plans were being made to by-pass the Big Jack with a new road.

The railway reached Cooma from Queanbeyan in 1889, the same year as the Brown Mt. road was completed, until this time, the route to Monaro still used by most Shire groups was by the Big Jack or Tantawanglo. Places like Bemboka were somewhat isolated areas of the Twofold Bay region. It was planned that the railway, after reaching Bombala, should continue to Bega and Eden, so three surveys were carried out to find a line down the mountain. One of these, in about 1895, was carried out by Charles Darragh, the son of a Rocky Hall selector, Felix Darragh. Charles left home as a youth and gained qualifications in surveying, astronomy and other scientific pursuits. During his time in the Bega valley he often viewed the lofty mountains of the region. While carrying out his survey, he described how he reached the mountain summit:

"When I reached the top of that lovely viewpoint what a sight I beheld. I could see the vast Pacific gleaming in the sunlight and the intervening Far South Coast area from the Tilba country and Mt. Dromedary to Mt. Imlay on the south of Twofold Bay, a glorious panorama."
(Pambula Voice 12.2.38)

The State Geodetic Branch named the mountain after him. His survey route followed the Tantawanglo road to Candelo. Although the railway reached Nimmitabel in 1912, the Railway Junction Hotel in Wolumla waited in vain. Bombala was reached in 1921, but the roads to meet the train were remaining obstacles.

The economic conditions of the late 1920s created high unemployment, particularly on the coalfields of the Newcastle region. Residents of the Imlay Shire, then the southern areas of the present Shire, had been pressing for a road easier than those being used. To relieve unemployment, it was proposed to build this road from Wyndham to Cathcart following in part, the old Purgatory track to the east of Big Jack. The work began in 1928 and at any one time two hundred men were employed using horses, tip-drays and horse drawn scoops, the only mechanical device being a steam shovel.

To dispense with the need for bridges, the road has several hairpin bends and culverts, allowing also for easier grades. The two bridges required were constructed of concrete over the Jones and Mataganah Creeks. Completed in 1911, the road by-passed Rocky Hall and in spite of some early landslides in an area between the two bridges in 1934, it has since been an all weather road.

The mail contractor from Merimbula to Bombala on three days each week, Les Sharpe, now travelled a shorter and quicker journey. Not so Seward (Googy) Haig, who drove the cream lorry for the Pambula Butter factory, and still had to service the dairy farms of Cathcart and Rocky Hall. With the growth of road transport, the steamers ceased the coastal trade and the trains did likewise. Fred Piper is remembered having died on the Brown Mt. road shovelling snow. Fred drove the mail service from Bega to Cooma for many years. Passing the lookout named in his honour, one cannot forget the short man with hunched shoulders wearing a dust coat and cloth cap that seemed part of Cooma station on train days.

Travellers from the Bega Valley today would be most likely to use the Brown Mountain and the Monaro Highway. The more scenic route is through Mt. Darragh, where Charles Darragh's 'glorious panoramas' are still there to be experienced.