Another banner read “We don’t want Biden — we want revenge”.
The group was calling for “revenge for police murders, for imperialist wars and fascist massacres”.
The protesters were later met by a large group of police officers, who arrested eight people in connection to the demonstration.
Portland Police said the group of eight had been hit with an array of charges including criminal mischief, possession of a destructive device, rioting and reckless burning.
Police also allegedly seized batons, pepper spray, Molotov cocktails, knives and a crowbar from those they arrested.
Many of the protesters managed to escape police after damaging the Democrat headquarters.
“This is not the first time our building has been vandalised during the past year — none of the prior incidents have deterred us from our important work to elect Democrats up and down the ballot, and this one will be no different,” the Democratic Party of Oregon said in a statement.
Handymen were called in to repair the damage not long after its windows were smashed.
After a brief period of calm in Portland, protesters took to the streets again when night fell.
Portland Police said in a statement that they and federal authorities were forced to disperse a group of around 150 protesters when they began to graffiti the Immigration and Customs Enforcement (ICE) offices just after 9pm.
“A crowd of about 150 people walked from Elizabeth Caruthers Park to the ICE offices ... People in the crowd carried shields, umbrellas, ASP and PR-24 batons and picked up rocks on their way. Many people wore gas masks and helmets. Within a few minutes of arriving people began applying graffiti to the ICE building,” police said.
“At about 9.45pm federal officers emerged on the ICE property to move the crowd away. Federal officers dispersed to the north then took up a position about half a block away.
“Portland Police circulated through the neighbourhood during the next hour to find specific people in the crowd for whom there was probable cause to arrest and made arrests as they identified and located suspects.
“During that time the crowd dissipated a little at time. Eventually there were only a few dozen people milling about as officers finished making their last arrest. Portland Police did not deploy any munitions or CS gas.”
Large protests also kicked off in Seattle, where dozens of demonstrators dressed in black marched in the streets.
A handful of antifa protesters were arrested in the Washington city, however police kept a distance to ensure things stayed peaceful.
Videojournalist Brendan Gutenschwager, who regularly covers rallies across the US, captured the momenta protester was arrested.
American flags were burnt in the street and a number of businesses were broken into, but police have since managed to disperse the protesters.
“F*** Trump, f*** Biden too, they don’t give a f*** about you,” the protesters chanted.
And in Boston, a small group of protesters stopped traffic as part of their “No honeymoon for Biden” demonstration.
“On Inauguration Day a coalition of organisations are coming together to re-take the initiative for a progressive agenda with a rally on the Boston Common at 4pm,” an event page for the protest said.
“Security will be a priority as everyone will be asked to wear masks and practice physical distancing.
“A top priority will be to demand economic security for working people without wasting billions on corporate welfare.
“A real Green New Deal is necessary to create millions of good new jobs, recover the economy, and set us on a path for climate stability by 2030. The suffering and death caused by the coronavirus must translate into the political will to replace the current patchwork of private health insurance with universal health care.
“We also need real solutions to the other pandemic of police brutality with impunity that has burdened communities of colour for generations.”
Inauguration Day in Portland. A group of about 100 people dressed in black march thru Southeast Portland pic.twitter.com/cGhVhdTwGW