On the lower side of the entry from the Main Street to Mary Street was a tiny shop once owned by people named Munn, who made ladies hats, around the 1900/1925 period. On their death their daughter Minni lived there privately until the 1950s. On the upper side Tommy McCann had a Pub and a great appetite for gooseberries and this was one reason for him having his garden at the rear full of gooseberry bushes. When these were laden with fruit, he would call on his old friend Martin Cafferky, the School Master (on whom he was always playing tricks) to send a squad to pick the berries. The boys were delighted to get away but were warned by Cafferky that they would have to keep whistling any who stopped would be accused of filling their mouths and immediately sent back to school.
At the back of the Pub, Tommy had an old two storey house which was used by Pat ("B usky") Dorrian and his brother Dan, as a clothes store in the 1940s and later made into a piggery by Hugh, a son of Tommy McCann. Tommy McCann died on the same morning that Hugh got married and left the Pub to Hugh who later added a Footware Shop to the business, in the 1950s and worked there until he died, in 1979.
The Footware closed and the Pub was taken over by Sam Brannigan, a local who was a representative for a Spirit Firm. Some time later Sam handed over to O'Rourkes, strangers to the Town and who are still in occupation at the present providing all the singsongs and cabaret necessary to draw a custom in this age and time.
Hugh McCann was greatly interested in horseracing and actually ran a Bookies in the Town about the 1950s. One day as he walked up the street, he saw G. F. Annesley, filling up with petrol at Cuunninghams and asked him if he was going to the Races in Dublin. G. F. was and Hugh accepted the offer of a lift. On their arrival at the Race Course little over an hour later, Hugh thanked G. F. for both rides. "What do you mean, both rides?" asked Annesley. "My first and last!" answered Hugh and went to find another lift home.
George Wilson, "Toby";- If anyone was game enough to address him by that nickname, was a Boer War Soldier as stiff and as straight as a rush and as short tempered a wee man as ever sported a waxed moustache. When Toby spoke pleasantly to anyone, they thought it was their Birthday and this was the little man who opened a Watchmakers and Bicycle Shop next door to Minnie Munn in the 1900s. It took a lot of courage to face George in his den as a request for a new part for a bike was answered with a barrage of abuse and a charge upstairs to his stores which ended with cycle frames, mud- guards and wheels being flung about in very noisy protest. One wrong word from a customer and his life was in danger of termination by cycle frame strangulation. He treated his watch and clock customers with the same civility and many a person gathered his dismantled time piece from the street, but for all that, Toby was a real character and one of the most talked about men in the Town.
One wintry morning a neighbouring businessman was passing and got a shock to hear Toby calling him over and pointing to an old, and the only, man slithering up the street. Toby remarked "Thats the sort of an old B*****d that you and I have got to get a days pay out of." The neighbour, finding him in a talkative mood, stayed for a while until they noticed the old man returning down the street with a new spade over his shoulder and when he was just passing Toby said to him "Well it's going to a good home anyway."
George Wilson kept the old Markethouse clock ticking over until he died, about the middle 1950s. His and Minnie Munn's little shops were knocked into one, completely renovated and refronted in 1958. It is now a modern Confectionery owned and run by Mrs Leontia Connolly, Daughter-in-Law of the people who once owned Mooney Bros in the Upper Square. In practically every town there always was and will be people with the temperament of George Wilson and the most remarkable thing is the way they are remembered with reverence by their own community.
Boot and Shoe Sales and Repairs in John Hall's on the Main Street adjoining Toby Wilsons, known to be previously owned by Cunninghams (not the Bros.) was occupied by Halls since the 1830s and run by John Jun. and George on the death of the old man, John. In the 1930s the Halls were the real owners of Bustards. Bustard being a Son-in-Law was the Manager of the Factory for Hall and traded under that name. John Jun. served behind the shop counter while George, with a few employees, repaired the footware in a workshop across Mary Street. They also tinkered at radios and as a sideline charged wet batteries which were the main source of power for the countryman's wireless in the 1930s. The two Halls were very quiet men in later years but were lively enough in their youth. A lot of their leisure time was spent in the Electric Power Supply Station on the Circular Road, playing cards and all sorts of tricks on the people who frequented that place. A rumour was spread through the Town that witchcraft was practised in the Power House at night and with an invitation to anyone who wished to take part in this experience. The new arrivals were requested to place their hands on the tubular rail surrounding the running engine, the lights turned out and amid laughs from the spectators, the victim shook hands with 230 volts which brought him closer to his ancestors as he would ever wish to be.
Halls closed shop in 1955 and sold out. The whole premises were then completely renovated. With a new front and the shop divided into two. Jim Wilson, the Chemist and new owner, commenced business in the upper of the two shops while living above the whole lot. He rented the other shop to Dick McCabe, from Dundrine, for the sale of footware and as a sideline Dick had a mobile Grocery Van on the road. Dick McCabe was in occupation there from 1960 to 1964 and then moved out. Jim Wilson carried on until 1978, when Dan O'Rourke a local Plumber bought the whole place and opened a Wholesale and Retail Plumbing Business. Dan died in 1981 leaving two sons, Paddy and Donal to carry on. The O'Rourke Bros. soon expanded buying all of Ned McKenny's yard and part of Frank McKenny's property all being situated in Mary Street and adjacent to O'Rourkes. This Plumbing Firm is doing extremely well.
On the Main Street beside Hall's Footware, a Mrs. King had a Cafe and Boarding House in the 1900 period. One of her two sons Peter, a tall squarely built curlyhaired man, became one of the Town's colourful characters, dressing up as a cowboy and acting the fool on the local stages with 'Snow Paddy Cunningham' dressed as a woman. Peter tried many ways to get his hands on the ever elusive pound. He bought an old Tractor and Thresher and worked on the country, ploughed land for other farmers and had a go at the Pork Business. Peter said the more food he put into the pigs the thinner they got and often recalled the remark made by one of his pigs as he drove them to the Railway Station for shipment. "You'll not forget us for a while Peter." Working with pigs isn't a nice job at any time and Peter had no need to proclaim his occupation always to the displeasure of his mother with her Eating House.
Peter laughed this off and told a story about a man who called in the Cafe looking for him. His mother directed the stranger to Bunker's Hill where Peter had his Piggery. "How will I know him asked the man" and Mrs. King replied "He'll be the one with the glasses." In his younger days, about the end of the First World War, Peter worked at repairing bicycles in Willie Skillen's Jewelery and Bicycle Shop and at that tiem teh country was hit by a terrible flu, killing thousands of people and putting Willie, his wife and two sons off their feet. Peter King nursed that family through their illness as well as running the house and for that the Skillens were forever indebted to him
Shortly after that, the Kings emigrated to America but returned in the 1930s to carry on the Cafe until 1946 when Peter sold out and bought a Pub at Edindarrif. He moved there and spent the remainder of his days behind the Pub counter. During the years the Kings were away, the Cafe was rented to Peter Mageean, from the New Row, to carry on his Barber's Shop. This was one of the old time Hairdressers with the long stools around the inside of the shop and usually heaped with Vernons and Littlewoods Pool Coupons. Instead of a name above the door, there was a six foot red and white striped pole sticking straight out across the footpath. On the return of the Kings Peter Mageean moved to Downpatrick depriving Castlewellan of one of it's best entertainment spots. Peter died in 1986. It is thought a man called Carr from Ballykinlar, repaired footware in Kings about the 1940s but was there only a short time. During the early 1980s when this place belonged to John McKenny, one young fellow, "Brogan", from Kilcoo started a Green Grocery, but his stay was limited to months.