The first stopping place beyond Moss Vale was at Meryla Siding, where a platform existed from 1883 to 1969, serving the locality of Werai.

Today Exeter Station is the first stop. The pioneer there was James Badgery, whose initial grant was issued in 1822. His son, Henry, consolidated grants in the area, naming his property Vine Lodge. The railway line bisected his holdings and a station opened as Badgery's Siding in 1878. The name was changed to Exeter in August 1890, when a fully inter-locked crossing loop and new goods siding were installed. A large section of the Vine Lodge estate was subdivided in 1891 and a village developed. Elegant timber platform buildings, still in existence today, were erected at the station.

Next down this section of line is Bundanoon Station, which recently has been refurbished to preserve its heritage features. It began in 1868 as Jordan's Crossing, a stopping place with gated level crossing and water tank, so named because the railway ran through land owned by the Jordan family and perhaps also referring to a nearby crossing loop for up and down trains to pass.

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By 1877 a siding was added along with a small station comprised of a waiting shed and wooden platform which allowed travellers to step across to the carriage rather than climbing up from ground level. Originally known as Jordan's Siding, in 1881 the station was changed to Bundanoon, that being the residents' chosen name for the village and post office. The name reflected the Gundungurra word meaning 'deep gullies' as recorded by Charles Throsby when exploring the area in 1818.

By 1882 the station had gained a larger platform and a new parcels, ticket and telegraph office, with separate waiting rooms for ladies and gentlemen, and a ladies' toilet. A goods shed was also erected. Tourists began to arrive by train, attracted by the spectacular beauty of the nearby gully country and the clean air. With them came the need for more accommodation, recreational facilities and tracks to scenic vantage points. The fledgling village began to flourish, eventually becoming the Wingecarribee Shire's fourth town.

When the Moss Vale to Marulan section first opened in 1868, there were no intermediate stopping places south of Bundanoon, but eight were later opened.

Several of these were in the locality of present-day Penrose village. A siding opened in 1869 and was first mentioned as a passenger stop in 1 June 1871, under the name Cable's Siding. This was situated southward of the present village, near where the Arcadia fruit stall operated on the Highland Way for many years. A 31-metre platform and waiting shed were erected by 1892 and in 1897 the station was renamed Penrose.

Another station, first mentioned in the timetable of 1 May 1885 under the name of Wollondilly, was an unattended platform situated near where the present Penrose Public School Zone speed restriction starts (near Dunlop Lane). When a crossing loop was built in 1890, it became a staffed station and in June 1891 was renamed Kareela, an Aboriginal word for 'south wind'.

On duplication of the southern line between Bowral and Goulburn, undertaken during 1915, the Railway Commissioners decided that the locality did not warrant two stations close together. Penrose and Kareela stations were closed and a new Penrose Station was built midway between the two, opening on 14 March 1915. A new post office was erected nearby and the locality prospered with extensive orchards.

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