The stony-faced pet has become something of an internet sensation with his persona 'Dog in a Bag'.
Hailing from London, Timothy has recently been on a holiday tour of Shropshire and his owner Rory Fox has been documenting his travels on twitter and on his website – doginabag.co.uk
Timothy has managed to see Ironbridge, Bridgnorth and Ludlow during his tour all from the comfort of a Royal British Legion poppy jute bag.
In 2013 Timothy suffered a seizure as a result of an enlarged heart whilst out on a particularly long walk in Camden.
That means he finds it difficult to walk, so he lets his owner do all the hard work instead.
Rory, 36, recalled the incident, saying: "When it happened at first I thought he was dead in my arms."
The condition is more common among elderly dogs and Timothy, being 11, has already lived past the average lifespan for a King Charles spaniel which is nine years.
However, despite this, Timothy is able to live a perfectly happy and full life if he doesn't have to walk for longer than 20 minutes at a time. So his owners came up with the plan to carry him around in a bag.
This stroke of genius meant Timothy was able to continue his travels with Mr Fox as well as giving him the opportunity for internet stardom.
Rory said: "People in London were always asking us for photos of Timothy in his bag, so we thought we might as well document his travels ourselves."
He set up doginabag, documenting all the latest photos of Timothy on his travels, including many of his latest trip to Shropshire where he saw some of Shropshire's finest attractions including Ironbridge, Blist Hill and the Severn Valley Railway Station, at Bewdley.
Though Rory was surprised to see how far his dog's fame had spread when he visited Blist Hill with him.
"Unsurprisingly I've never been stopped in the street before and been told 'I've seen your dog on the internet' but it happened six times while we were there," he said.
Timothy's also visited Yorkshire with his owners last summer and he's been treated to several dog themed days out for his birthday.
These have taken him to Berkhamstead, Canary Wharf and Barking.