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First Peoples.
The earliest inhabitants were peoples of distant descent in the subregion, later to be called 'Bushmen' [or 'Bosjesmans' (Dutch) or 'Boesmans' |(Afrikaans), all now considered derogatory], now San (although this too has negative connotations). Their way of life was as hunter-gatherer and they not given to the making of permanent settlement, natural shelters- such as caves, overhangs or scrub shelters being their customary habitations.
They were followed, and intermixed with the Khoekhoen, the clan of this region when the pioneer Dutch settlers arrived, known to themselves as Hessequa. They were transhumant peoples who made semi-permanent settlements at water sources where they could also graze their landrace sheep, goats and few head of cattle. They used pack-oxen to carry their 'matjieshuis' material - flexible staves and woven rush mats - which would be erected where they settled. Many of the place names and geographical features of the greater region still bear these traditional names, such as the nearby Heskwas River and Tradouw Pass. The many places suffixed -kraal allude to these settlements, the kraal being etymologically linked to their word for a corralled area protected by stones, thorn scrub and even living aloe hedges or coral trees enclosures (anecdotally a word that travelled by way of the early Portuguese to become part of the European tongue). Many place names in the vicinity derive their names from local clan chieftains or leaders, such as Lang Elsies Kraal in the Bontebok National Park. Slanghoek, a rural town to the east of Swellendam was a grant to the local Hessequa by the Crown in the time of Victoria. Suurbraak has a similar history and became centre to a population of freed slaves as well after their emancipation in 1836.
Company rule.
With the arrival of the white settlers the indigenes way of life was irredeemably disrupted, first through a collapse of their economies, both of livestock as wealth and land occupation systems, unreconcilable with that of Europeans, later through disease such as smallpox where populations were decimated, and finally through a natural intolerance to the consumption of alcohol which led to addiction and destitution.
The Dutch VOC had set up a permanent revictualling station in the Cape in 1652, but as the settler numbers increased and more became Free Burghers, these persons traded and later moved and settled ever further from this centre. Baron van Imhoff on a brief visit to the Cape in 1743, on his way to Batavia, made a short tour of the country. Of his recommendations to the Company was that the 'Overberg' - the land beyond the Hottentots Mountains - be raised to the status of a sub-drostdy of the then Drostdy of Stellenbosh. Theophilis Rhenius was appointed as Assistant-Landdrost-cum-Secretary, later promoted to full Landdrost. To house these offices a Drostdy was erected in 1746-47.
From about 1787 the Cape government had an understanding that the farmers of Swellendam would deliver wheat at a fixed price to the Company's granary at Mossel Bay. This agreement was terminated in the mid 1790s to economize on the expenditure of the Company. This led to a general dissatisfaction with Company rule throughout the distant centres of the colony, including Swellendam and Graaff Reinet.
In 1795 a band of armed men occupied the Drostdy and declared a Republic in an attempt to free the Burghers from Company rule.
British Interregnum
With the British invasion of the Cape in September 1798 a detachment of Burghers from Swellendam hastened to assist the defenses there but with the surrender to the British, persisted in using the name 'Colony of Swellendam' on official documents. The first Church was built in the time of British occupation in 1802.
The brief period of the Batavian Republic 1803-1806
Under Batavian rule wool sheep were introduced to the Overberg in 1803.
British Colonial rule 1806-1910
With the colonization of the British in 1806 agriculture flourished. The Swellendam Agricultural Society was formed in 1832, the agricultural show the longest continuous running in the country. With the emancipation of the slaves a church was erected, termed an Oefeningshuis-', to circumvent restrictions on it being called a church. A family of Muslims, the Hendricks - probably of slave descent - became known for their skilled plasterwork while other skilled Muslim artisans located in Lemmetjiesdorp near The Glen, offered valuable service to the making of the fine built heritage of Swellendam. Swellendam became headquarters to the Barry family, merchants and traders who established a harbour at Malgas. An historic signaling canon used to alert farmers to the arrival of their steamship, the 'Kadie' in the harbor, is still located just outside Swellendam adjacent the N2 before Stormsvlei. Many of the structures in the town and district are associated with the Barry's such `as the Auld House,the Barry House, and father afield in Port Beaufort the Barry Barn and Barry Church, and in the Tradouw Pass, Letty's Bridge. A severe drought in the 1860s brought a bad depression to the area and the Barry enterprise flounders, the sinking of the ship, The Kadie in November of 1865 dealing a fatal blow leading not their bankruptcy in 1866. The town was also ravaged by a disastrous fire in 1865 destroying many of the older structures of the town centre, including many houses, the hotel, printing press, bank and Wesleayan Chapel (SHA 2018:11).
Mossel Bay replaced Port Beaufort as the main trading harbour and Swellendam importance as a trading, and with that as a church centre declined as other towns grew in importance such as Caledon, Riversdale, Heidelberg and Bredasdorp.
After Union (1910-present)
In 1965 the main road through the town, Voortrek Street, was broadened leading to the felling of many of the oaks that lined the historic street, while many of the buildings were demolished or lost their street frontages, forever adversely damaging the historic character of the once rural town. Ironically had the damage no sooner been done that the main road, the N2, was realigned outside the borders of the town centre in the 1970s. This, probably intentionally, coincided with the enforcement of the Group Areas Act in the 1970s where the so-called 'Coloured' population was relocated to Railton across the highway divide, the Golf Course re-established from there where a little vernacular settlement existed, to the 'White' side of town towards Marloth Park beneath the Langeberg. This demographic divide persists till this day. (SHA 2018:12-13) List of references:Buirski, AP; Langenhoven, AH (Editor) . 2017. The Barrys, the Overberg, and the harbour of Port Beaufort. Witsand: Privately published by the Editor. pp Various
| Burrows, Edmund H. . 1988. Overberg origins : The English-speaking Swellendam families. Swellendam: Private (Swellendam Trust). pp All
| Burrows, Edmund Hartford . 1994. Overberg Odyssey : people, roads and early days. Swellendam: Privately printed in co-operation with the Swellendam Trust. pp 5-7, 9-14, 17, 18, 24, 26, 28, 35-43, 48, 53, 58-61, 70, 71, 77, 82, 86-88, 93-96, 98, 70, 71, 77, 82, 86-88, 93-96, 98, 102, 106, 110, 112, 116-122, 124, 128, 138-143, 145-147, 152, 157, 162, 164, 166, 175, 180
| Cleary, Melanie and Du Plessis, Karen . 2006. Overberg, The : Inland from the tip of Africa. Cape Town: Struik. pp 158-161, 173, 174
| Fransen, Hans. 2004. The old buildings of the Cape. A survey of extant architecture from before c1910 in the area of Cape Town - Calvinia - Colesberg - Uitenhage. Johannesburg & Cape Town: Jonathan Ball Publishers. pp 453-463
| Fransen, Hans. 2006. Old towns and villages of the Cape. A survey of the origin and development of towns, villages and hamlets at the Cape of Good Hope. With particular reference to their physical planning and historical landscape. Johannesburg & Cape Town: Jonathan Ball. pp 88-96
| Howard, Leslie & Phillips, Keith. 2004. Overberg tapestry. Helderberg: Keith Phillips Images. pp 9-10, 18-19, 21, 24-30, 36, 45, 51, 55, 68-69, 71-74, 76-79, 83, 85, 89, 91, 95, 107, 109, 111, 116, 118
| M. E. R. & Rothmann, A. 1960. The Drostdy at Swellendam. Swellendam: Drostdy Commission. pp All
| Maeder, GA & Zinn, C. 1917. Ons kerk album van Hollandsche kerken en leeraren. Capetown: Cape Times. pp 42
| Oberholster, JJ. 1972. The historical monuments of South Africa. Cape Town: Rembrandt Van Rijn Foundation for Culture at the request of the National Monuments Council. pp 109-115
| Picton-Seymour, Désirée. 1989. Historical Buildings in South Africa. Cape Town: Struikhof Publishers. pp 80-81
| Potgieter, DJ (Editor-in-chief). 1974. Standard Encyclopaedia of South Africa [SESA] Volume 10 Sle-Tun. Cape Town: Nasou. pp 386-387; 387-388
| Richardson, Deirdré. 2001. Historic Sites of South Africa. Cape Town: Struik Publishers. pp 153-156
| Rothmann, ME en A . 1968 (1960). Drostdy op Swellendam, Die. Elsiesrivier: Raad van Kuratore. pp All
| Schoeman, Chris . 2017. Historical Overberg, The. Cape Town: Zebra Press. pp 9, 18, 19, 34, 52-60, 189, 191, 192, 195
| Scott, Ann and Scott, Mike (Compilers and producers) . 2001. Overberg explorer, The : a guide for environment-orientated travel in the Cape Overberg : a joint project of the Overberg community. Gansbaai: Overberg Conservation Services. pp 83, 84, 170
| Swellendam Heritage Association . 2023. The Irrigation Water of Swellendam. Swellendam: Swellendam Heritage Association. pp All
| Thomas, Beverley, van Hemert, Marena & Cochrane, Colin . 1997. The Drostdy Museum : Guide Book. Swellendam: Drostdy Museum. pp All
| Thomas, Beverley (Compiler). 1995. The Drostdy in Swellendam : a pictorial history. Swellendam: Drostdy Museum. pp All
| Tomlinson, LL. 1943. Geskiedkundige Swellendam. Cape Town: Nasionale Pers Beperk. pp All
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List of structures:Auld House: 1802.  
| Barry House: 1846 : 1860.
| Berg Street, No 27 - Historic House: 1900.
| Berg Street, No 30 - Historic House: 1870c.
| Berg Street, No 31 - Historic House: 1870c.
| Berg Street, No 33 - Historic House: 1870c.
| Berg Street, No 46 - Historic House: 1880c.
| Berg Street, No 53 - Historic House: n.d..
| Bethel Hall: 1935.
| Bethel Street, No 72 - Historic House: 1860c.
| Bloemfontein Huisie: 1922.
| Bontebok National Park Chalets: n.d..
| Braeside: n.d..
| Bramble Bush: 1905c.
| Buirski & Co: 1880s.
| Buitenkant Street, No 3 - Historic House: n.d..
| Buitenkant Street, No 5 - Historic House: 1900.
| Buitenkant Street, No 7 - Historic House: n.d..
| Buitenkant Street, No 82 - Historic House: 1890c.
| Bukkenburg House: c1890.
| Cattle Dip / Dipgat: 1920s. Hermitage,
| Charcoal Kiln on Voorhuis Farm: 1750s
.
| Christ Church - Anglican: 1911. Swellendam Central,
| Christ Church - Anglican: 1856. Central,
| Christ Church Cemetery: n.d..
| Church Street, No 10 - Historic House: n.d..
| Church Street, No 24 - Historic House: 1870c.
| Coachman, The: n.d..
| Coniston - Paulsen House: 1822.
| Cottage, The: 1832.
| Cypress Cottage: 1815.
| De Kloof - Weltevreden: 1801.
| Drinking Fountain: n.d..
| Drostdy Museum Complex: 1934-.
| Drostdy Museum Complex - Conservation Building: 1986.
| Drostdy Museum Complex - Gaol: late 1700s onwards.
| Drostdy Museum Complex - Mayville: 1853.
| Drostdy Museum Complex - Mayville Memorial Rose Garden: 1977.
| Drostdy Museum Complex - Trades Yard : Ambagswerf: 1969-1974.
| Drostdy Museum Complex - Zanddrift: 1734 : 1769 : 1976.
| Drostdy Museum Nursery: n.d..
| Drostdy Street, No 5 - Historic House: n.d..
| Drostdy, The (Now Drostdy Museum): 1746.
| Evening shade: 1860c.
| Farm Church: 1950.
| Faure Street, no 12 - Historic Cottage: 1860c.
| Gaoler's Cottage / Sipierhuis [Warden's House] / Old Post Office: 1828.
| Gates to Powel Sports Fields - B.I.C. van Eeden Memorial Arch: 1952.
| Glen The: 1812/1821.
| Hermanus Steyn Street, No 10: 1890c.
| Hermanus Steyn Street, No 12: n.d..
| Hermanus Steyn Street, No 6: n.d..
| Hermitage School: 1911.
| Hoek's Garage: c1940.
| Hope Lodge: 1839.
| Hopley House : 1839.
| Joubertsdal: 1792.
| Kerkplein - Church Square: n.d..
| Klein Drostdy: 1850.
| Klipriver Farm: 1833.
| Koornlands Cottage - The Cottage: 1832.
| Lemoenhoek School for 64 pupils: 1914.
| Lodge la Belle Alliance - Restaurant: 1924.
| Malta House: 1750.
| Masonic Hall: n.d..
| Memorial to the Coronation of King George V: 1911.
| Moolman Street, no 10 - Historic Cottage: 1850.
| Moolman Street, no 3 - Historic Cottage: n.d..
| Moolman Street, no 9 – Historic House: 1850.
| Moolmanshof: 1798.
| Morgenzon: 1745.
| Municipal Offices: n.d..
| Nederduitse Gereformeerde Kerk: 1911.
| Nederduitse Gereformeerde Kerk: 1798.
| Nederduitse Gereformeerde Sending Kerk Hermanus - Mission Church: n.d..
| Nederduitse Gereformeerde Sendingkerk - Voortrekker Hall: 1904.
| Nederduitse Hervormde Kerk: n.d..
| NG Kerksaal: 1954.
| Oefeningshuis - Meeting House: 1838.
| Old Library: 1907.
| Old Mill / Groenewald's Mill / Mill Cottage: 1840.
| Old Racecourse: n.d.. Bontebok National Park,
| Old Residency (Now Heemraden House): 1839.
| Old School: n.d..
| Olyfkrans College - Old Boy's High School: 1825.
| Olyfkrans College - Old Boys High School: 1825.
| Oslo House: 1850.
| Oupos: 1734.
| Park Villa: 1802.
| Pedestrian Bridge over the Koornland River: 2000s.
| Powder Magazine: 1850.
| Railway Station: c1935.
| Road Bridge over the Buffeljags River - 'Sugar Bridge': 1845-1852.
| Rose Cottage: 1840.
| Rothmann House (JVDS House and Cottage): 1834.
| Rotterdam: 1794.
| School: 1906.
| School: 1923.
| Schoone Oordt: 1853. Swellendam Central,
| Shalom: n.d..
| Shop: 1880.
| Siebert Street, No 9 - Historic House: 1900.
| Somerset Street, No 4/6 - Historic House: n.d..
| St Luke's Church: 1867.
| St Luke's School - First: n.d..
| St Luke's School - Second: n.d..
| Streicher Cottage: 1840c.
| Sugar Bridge: 1852.
| Swellengrebel Street, No 18 now Drostdy Museum Administrative Offices and Workshops: 1800s : 1853.
| Town Hall: 1885.
| Townhouses (Tuishuisies): n.d..
| Townhouses (Tuishuisies) - First: 1860.
| Townhouses (Tuishuisies) - Second: 1876.
| Van Oudtshoorn Road, No 11: n.d..
| Van Oudtshoorn Road, No 17 - Historic House: n.d..
| Van Oudtshoorn Road, No 3 - Historic House: n.d..
| Van Oudtshoorn Road, No 7 - Komnader: 1928.
| VOC Memorial - Oude Post: 1941 : 2007.
| Voortrek Street, No 101: 1890.
| Voortrek Street, No 124/126 - Historic House (Now two shops): 1850s.
| Voortrek Street, No 128 - Historic House: 1844.
| Voortrek Street, No 130 - Historic House: 1844.
| Voortrek Street, No 132 - Historic House: 1798.
| Voortrek Street, No 134 - Historic House: 1844.
| Voortrek Street, No 143 - Historic House: 1860c.
| Voortrek Street, No 145 - Historic House: 1850c.
| Voortrek Street, No 177 - Historic House: 1880c.
| Voortrek Street, No 179 - Historic House: 1860c.
| Voortrek Street, no 184 - Historic Cottage: 1860c.
| Voortrek Street, No 19 - Historic House: 1802.
| Voortrek Street, No 190 - Historic House: 1840c.
| Voortrek Street, no 198 - Historic Cottage: n.d..
| Voortrek Street, no 200 - Historic Cottage: 1840c.
| Voortrek Street, No 204 - Historic House: n.d..
| Voortrek Street, no 204 - Victorian House: 1890.
| Voortrek Street, No 233 - Historic House (was Groenewald's Mill): n.d..
| Voortrek Street, No 236 - Historic House: 1850c.
| Voortrek Street, No 270 - Historic House: 1834c.
| Voortrek Street, no 276 - Historic Cottage: n.d..
| Voortrekker Monument: 1938.
| Watermill: 1880.
| Weltevreden: 1801.
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