One of Ludlow's biggest annual events, the Medieval Christmas Fayre, had to be cancelled on Saturday after high winds had ruined the set up inside the castle overnight.
The town council's Christmas lights switch-on event has also been cancelled, which would have seen crowds gather in the square with an appearance from Santa Claus on Saturday evening.
Inside the castle, stalls and tents were damaged so severely, and with strong winds still going during the day, that organisers Abi and Prue Dakin made the difficult decision to cancel the event.
The fair had already been cancelled last year due to the coronavirus pandemic, meaning the mother-and-daughter team who form Dakin Events were really looking forward to this year's event.
They said they had "no words that can truly express how we feel right now" after the event – which was meant to run Saturday and Sunday – was once again cancelled.
The pair said the devastation was beyond anything they had ever experienced during their time running events at Ludlow Castle.
Abi said: "The cancellation of the Ludlow Medieval Christmas Fayre this weekend because of the damage caused by Storm Arwen has been absolutely devastating.
"Immeasurable damage has been done to the marquees and to the exhibitors' stalls, many of whom were set up prior to the storm hitting.
"We have been overwhelmed by messages of support and are hugely grateful for all the help we have received on site here today as well.
"We would ask that people still support our exhibitors by buying from them online – many of them have lost so much this weekend. You can find the link to all our exhibitors on our website.
"In terms of the future of our beloved fayre, we will be releasing a statement early next week, and will be contacting all those who purchased tickets for this weekend direct.
"This weekend would have been Prue’s 30th year running events in Ludlow Castle, and 15 years for me. It goes without saying that we have never experienced anything like this before and it is truly heart-breaking for all involved."
The pair have also encouraged people to support the stallholders who will have lost out on sales from the weekend.
People are encouraged to do their Christmas shopping from home by supporting exhibitors from the fair.
Visit www.ludlowmedievalchristmas.co.uk/exhibitors to offer support.
The owner of Fuffle from Fudgeheaven, a confectionary business based in Bromsgrove, was meant to be one of the stallholders at the fair.
He said he had spent the morning helping to rescue anything he could from people's damaged stalls, as his had survived.
In a Facebook post, the owner said: "Sadly Ludlow medieval Christmas fayre has had to be cancelled due to the devastation caused by last night's winds.
"There's a lot of stallholders here crying a lot. I was lucky and my stall survived.
"I've spent the last hour helping the poor people whose stalls were devastated rescue what we can."
Andy Boddington, Ludlow town councillor, said he had never experienced winds like that in Ludlow before.
"Just after midnight it was unbelievable you couldn't stand outside," he said.
"Then at 4am a tree crashed down into my front yard – that was the case all over the town.
"It's not safe to hold events during these conditions and it's really sad for the organisers because it has been cancelled two years in a row now because of Covid previously.
"We are finally getting events under way again in the town but the winds overnight wrecked the events. They simply can't go ahead.
"It is a blow to the town as we are trying to recover from Covid as well. It's unfortunate because the medieval fair is a big event, it's fantastic, but it just couldn't go ahead really.
"The town council will still be turning on the lights later but with no crowds."