The road was constructed in pursuance of an act of Parliament, the
Battle Bridge and Holloway Road (Middlesex) Act 1825 (
6 Geo. 4. c. clvi), obtained by the Battle Bridge and Holloway Road Company. The company built the Caledonian Road in 1826 as a
toll road to link the
New Road with Holloway Road (which is part of the
Great North Road) and provide a new link to the
West End from the north. Originally known as Chalk Road, its name was changed after the
Royal Caledonian Asylum for the children of poor exiled Scots, was built in the area in 1828. The building has since been demolished and its site is occupied by local authority housing, the
Caledonian Estate built 1900–7. The first residential buildings on the road were Thornhill Terrace (numbers 106–146), which were built in 1832, and other terraces, which were built in the 1840s. From around 1837 to 1849, cottages in gardens were built between Brewery Road and the site of the railway which were part of the failed Experimental Gardens or French Colony founded by a philanthropist,
Peter Baume. Due to poor lighting and roads, the cottages declined into slums.
Pentonville Prison was built in 1842 immediately to the south of the asylum. Cattle drovers passed along the road on their way to
Smithfield until 1852 when the
City of London Corporation transferred the
Metropolitan Cattle Market to the Caledonian Market. In the mid 20th century, many communities were attracted to Caledonian Road by its relatively low property prices. An Irish community grew there; and in 1955, a cache of weapons belonging to the
Irish Republican Army was discovered in the cellar of No. 257 Caledonian Road. In the 21st century much of the commercial and residential property on the road has come under the ownership of notorious rogue landlord Andrew Panayi, one of England's biggest private landlords, who owns at least 200 properties on Caledonian Road alone.{{cite web|title=Landlord forced to submit 140 applications to prove flats are lawful |work= The Guardian == Buildings ==