Rupert lives in a cottage in Nutwood village with his parents, Mr and Mrs Bear, and is recognisable in his red jumper and yellow checked scarf and trousers. The family have an annual summer seaside holiday and occasionally also visit Rupert's aunts and uncles.
Rupert's closest chums are Bill Badger, Algy Pug, Podgy Pig and Edward Trunk, an elephant.
An assortment of animal chums appear with Rupert, including Pong-Ping, the Pekinese, 'Rastus Mouse, Willie Mouse, Ferdy and Freddy Fox, Reggie and Rex Rabbit, Lily Duckling. The stories also feature human characters - the Professor, Sailor Sam, the Chinese Conjurer and his daughter, Tigerlily, and the Sage of Um, who travels in his upturned umbrella, are often seen.
Adventures involve journeys to the bottom of the sea, King Frost's Ice Palace, the Weather Clerk's headquarters and numerous locations, where Imps and Elves are sometimes encountered. Ingenious inventions enable Rupert to fly to far away places quickly.
Many characters and friends join Rupert in his stories, which usually begin with him leaving Nutwood, enjoying an adventure, and then returning safely home.
Bill, one of Rupert's closest chums, always looks on the bright side. He shares many adventures, and is a long-standing pal Rupert relies on. Bill has a good sense of fun, and lives with his parents and baby brother in Nutwood.
Algy likes playing practical jokes, and is a close fun-loving friend of Rupert. He likes being out of doors, enjoying adventures in the countryside with Rupert and his pals.
The cheerful elephant pal is strong, and always tries to help his friends. Edward lives in Nutwood with his mother, father and baby brother, Pompey.
A greedy, good-hearted pal, Podgy is often lazy. However, he joins in with the chums in many adventures. His favourite pastime is eating food. His cousin Rosalie appears in some stories.
The brainy Bingo loves inventing, and is good at making things work. He is one of Rupert's pals, although occasionally he goes off by himself.
The young daughter of the Chinese Conjurer often misuses magic, which causes problems for Rupert' in his adventures. Tigerlily is mischievous, but usually helps put matters right.
The adult inventor friend of Rupert lives in a castle tower. The Professor has invented many flying machines, and often they are the cause of many exciting adventures.
The Pekinese friend of Rupert lives in Nutwood with his pet dragon, Ming. Sometimes Pong-Ping travels to China using his special lift. Although occasionally quick tempered, Pong-Ping is a good chum.
The country mouse enjoys adventures with Rupert. Rastus who wears a brown tweed suit is less shy than his cousin Willie.
The timid Willie is one of Rupert's closest chums. He is able to squeeze through gaps, due to his size.
The identical brothers are mischief-makers, playing tricks on Rupert. They attend Nutwood school.
Rupert's parents are used to their son going off on adventures, and welcoming him home on his return. Mrs Bear is often busy about their cottage whilst Mr Bear tidies up the garden.
Recognisable in her bonnet and cape, Lily is seen around Nutwood village. A friend of Rupert, Lily is timid and inquisitive; she is aware of what is going on.
An adult seafaring friend, Sam lives in a shack on the edge of Nutwood. He takes Rupert for rides to the seaside in his motorcycle sidecar, and is involved in many sea adventures.
The father of Tigerlily has magic powers and can cast spells. He lives in a pagoda in Nutwood.
The eccentric, wise old man flies in his brella - an upside-down umbrella. He lives on Um Island with a band of unicorns.
The identical twins are in Rupert's class at Nutwood school. Dressed alike, they enjoy sharing in Rupert's fun and games.
Clara is involved in a recent story, having moved from Nutchester to Nutwood.
Nutwood's village policeman is always friendly, and has a sense of fun.
He often makes use of Rupert's help in solving crimes.
The kind, mysterious Wise Old Goat is clever. His home is in a castle near Nutwood.
The gipsy boy has a good knowledge of the countryside, and understands nature. Rollo lives with his granny in a gipsy caravan.
Dr Uncle Bruno occasionally visits Nutwood in his motor-car, bringing presents for his nephew, Rupert.
Small, inquisitive Gregory is prone to mishaps. He is part of many adventures.
The young girl lives in Nutwood Manor, and is a friend of Rupert. Ottoline plays the piano.
One of Rupert's pals, Billy is a grandson of Granny Goat, and a nephew of the Wise Old Goat.
The scarecrow is able to talk, and walk around on his wooden legs. Odmedod is a good friend of Rupert.
Dinkie is Girl Guide Beryl's black cat, and is often with her.
The servant lives with the Professor, and helps with inventions.
The understanding schoolmaster at Nutwood school teaches Rupert and his chums.
The old countryman has lived in Nutwood for many years. He enjoys hearing about Rupert's exploits.