Young and old and from all walks of life, stood in freezing temperatures at The Quarry in the county town with banners. In front of them was a line up of shoes to represent those unable to protest.
The demonstration was against Clause 59, which would make it a crime to “intentionally or recklessly” cause public nuisance without a reasonable excuse and be punishable with a year in jail from magistrates or up to 10 years in the worst cases convicted at crown court.
Activists also took to the streets in cities including London, Bristol, Coventry, Newcastle, Liverpool, Manchester, Sheffield and Plymouth, ahead of a crucial vote on the bill in the House of Lords on Monday.
Protesters describe it as a draconian crackdown on the right to assembly, freedom of expression and other civil liberties.
Shrewsbury's Park Run was held while the protest took place, and many of the runners waved their support as they ran past.
Athlete, Mike Frost, finished his 5k and then joined the demonstration.
"The right to protest is fundamental," he said.
"This bill is just part of the creeping authoritarianism in this country. To think that someone could face the same sentencing powers for banging a drum at a protest as those in court for sexual assault is appalling."
Adam Shipp also said he was in the Quarry to help protect the right to protest.
"It is a right we enjoy in the country and over many years it has played a huge part in shaping the country, from the Kinder Scout protests to the Trade Union protests.
"I needed to be here for future generations, to protect their right to protest."
Jonathan Sanchi and Will Mewett, both in their 20s, travelled from Ellesmere and Petton to take part.
"I don't want to see the police given any more powers to use against democracy," Will said.
"The police did their utmost to disrupt the Sarah Everard vigils after her murder."
Jonathan said it was important to make sure the government knew the extent of the feeling against Clause 59.
The display of empty shoes was praised by protestor, Dave Ashford.
"They are very moving and represent those who are not here, unable to protest."
Shrewsbury resident Rachael Hindle said history proved the importance of peaceful protest.
"You only have to look back at the peasants' protests, the Tolpuddle Marches, the suffragette movement and others across history to see the value of demonstration."
Demonstrators from Labour, Liberal Democrats and the Green Party all took part.
Emma Bullard from the Greens said the party's two peers in the House of Lords were leading the fight against the Bill.
"Recently those who have carried out peaceful protest have been acquitted in trials, juries are standing up for the rights of peaceful protest," she said.
"It has been claimed that the silent majority want the protestors to go away and shut up. But many are grateful that the protestors are speaking up for them.
"Last year a local XR member did two protests where she sat in the road on her own - in Shrewsbury and in Bridgnorth. She said people were very kind to her, coming to speak to her and offering to bring her food, and one person even sat with her. The people being kind included people in the vehicles that were being obstructed."
Liberal Democrat councillor for Meole, Bernie Bentick said: "This type of restriction on the ability to protest was seen at its worst in the 1930s in Germany and an attack on democracy by the current, disgraced, Conservative Cabinet."
"I am delighted that so many people have turned out on a freezing morning to defend their right to protest."
Councillor Elisabeth Robers from Harlescott said it was good to see cross party support for the demonstration.
"We should have the right to be able to protest against those who represent us.
"People have had enough and protests like this are what we are left with."
About 150 people also turned out in Newtown.
The demonstrators, some with drums, others carrying placards, stood in the main street in the town to raise awareness of the bill.
Welsh Liberal Democrat Spokesperson for Montgomeryshire Alison Alexander addressed the protest.
Speaking afterwards said: “There is a balance to be struck between the inconvenience protesters cause to the public and the value of protest to society. This Bill fails dismally to strike the correct balance.
“That's not just the view of the Welsh Liberal Democrats, that's the view of former Prime Minister Theresa May, of Parliament's Joint Committee on Human Rights and of 109 Professors of Law from top UK universities.
“The restrictions to protest are excessive, the penalties are excessive and the powers the Bill grants to the Home Secretary are wholly unacceptable in a healthy democracy. It is not just about the large protests you see on your TV, but also more local protests like those to save your local school or A&E being shut.
“We must not allow hard won rights to be taken away and we must not be silenced."