Holloway used to be in Middlesex. It was a small settlement for many hundreds of years. The reason that Holloway is called this has led to many heated debates by historians over the years. The less glamourous and, in our opinion, more likely reason for the name is simple. It is believed that Holloway came from ‘Hollow’ or ‘Hollow way’ due to a dip in the road. This dip was caused by the many animals crossing the road. At the time, Holloway was the main route used by farmers bringing cattle into London for sale. At the time, Liverpool Road (then called Back Road) was used to rest the cattle and allow them to graze. So, we know for certain that Holloway was a rest stop for cattle on the way to market. The name of this village then seems to make a lot of sense.
The other theory for the name is a bit strange. It is said that Holloway was one of the main pilgrimage routes to Walsingham. That is about as much of this theory that exists nowadays. Could Holloway have changed from ‘Holy Way’ or did the pilgrims cause a dip in the road like the cattle in the other theory? Well, no one knows!
We do know that Holloway was pretty much just a road for many hundreds of years. It passed through two ancient villages: Stroud and Tollington. There was likely a settlement at Holloway perhaps acting as a service station for passers-by, but it was nothing like the Holloway we know today.
Holloway was mostly rural until the 1900s. Much like the rest of the settlements outside of London, Holloway was absorbed by the city during extensive building work as the railway came to town. This small settlement certainly has a very interesting history, no matter which naming theory you believe!