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Two Shaun the Sheep sculptures have been vandalised leaving organisers “heartbroken”.
The Heart of Kent Hospice, which organised the art trail, says up to £10,000 worth of damage was caused over the weekend.
More than 100 sculptures of the iconic animated character have been dotted around the county town since July 1 in partnership with Maidstone council.
When some sheep went missing from the map questions were asked about what had happened to them but the charity said they were removed for repairs caused by general wear and tear.
But over the weekend two sculptures were deliberately damaged resulting in them being permanently removed from the trail.
CCTV footage viewed by the charity showed “Shikki” Shaun sculpture, which was in the balcony area of Fremlin Walk, being vandalised.
The “Cherry” Shaun sculpture in Brenchley Gardens has also been wrecked.
Project manager for the initiative Erica Snow said: “We are absolutely heartbroken.
“The severity of the damage means that neither sculpture can remain on the trail and at this stage we know that Cherry is completely unrepairable.
“We’ve had to remove a couple of sculptures up until now because of wear and tear but this malicious damage has upset everyone.
“We would like to reiterate that these sculptures have been lovingly hand-painted by artists and their purpose, as well as to bring joy to people visiting them over the summer holidays, is to raise funds for Heart of Kent Hospice and our services to this community.”
There are less than three weeks left before people say goodbye to the sheep in Maidstone on August 30.
Between September 13 to 15 all the characters will be placed together in the Market Hall in Lockmeadow for a “farewell weekend”.
Later in the month, the hospice will be holding a charity auction at the Clive Emson Conference centre to give a Shaun their forever home.
The 51 large sculptures are expected to sell for £5,000 each, with all the proceeds raised benefitting the hospice.
Erica said: “Our Shaun Auction on September 26 is raising vital funds to support the hospice’s outstanding care services which are fundamental to this community.
“The loss to the charity of these two sculptures could be anything over £10,000 if we find that both are irreparable.”