Webb graduated Phi Beta Kappa from Reed College in 1998.
According to Webb: "I was riding a BMX bike down [NE] Alberta St. in Portland, Oregon with massive police response. [That was] on Dec. 30th, 1999." Webb engaged in "more naked activity in Eugene. . ." [Including] "several arrests and release without charge, [and] numerous encounters with police. . . My first [fully] naked bike rides were in Eugene. I participated in the Festival of Resistance and other activities, often top-free; sometimes naked. It became clear [to me] that Eugene police would not interfere with top-freedom . . ." [This was in the] "Spring - Summer [of] 2000"
Back in Portland, she "began, once again, to ride top-free during [monthly] Critical Mass (cycling) [rides.] "At first, I was threatened with arrest if I did not put [a] shirt on in public park, but in other instances, it was overlooked." She "went for [her] first nude bike ride and was stopped by police and held overnight for psych. evaluation." (Date Unknown). Webb continued, "The day following [my] release, there was a festival downtown. I stopped to listen to some music and took off my shirt. [Then,] I hopped on my bike and headed home. Police, familiar from the day before, stopped me and asked how everything had gone in the hospital, and why I had my shirt off? "We're not taking you anywhere today," they said. I said "The shirt was uncomfortable." The police told her not to distract anybody, as that could be cause for "disorderly conduct." Webb quoted them saying: "We've been watching you and you're not doing that." Webb said, "So, . . . It seemed this would now be condoned by police.
Webb was cited in Bend, Oregon on July 18, 2001, for disorderly conduct. Webb was in Bend on September 11, 2001. She wanted to bring a bit of life and levity to the extreme tragedy of the day, so she disrobed and rode through downtown evening traffic. According to an article in the local paper, she brought the levity and was not arrested. Terri said this was the "beginning of my publicity."
Webb appeared nude at her court date on November 7, 2001. She was arrested and sentenced to a year of supervised probation for contempt and ordered to undergo a psychiatric examination. Webb was due in court on April 23, 2002, "but that was postponed to Friday because, as District Attorney Mike Dugan put it, “she would not put on her clothes and told corrections officers that she would fight them if they tried to dress her.” It was decided that she would appear by live TV hookup from the jail for Friday’s hearing. The judge ordered Webb to be confined at Oregon State Hospital.
In 2002 Fred Foldvary, Ph.D. published an article about Webb: "A woman has been held in a mental institution in Oregon against her will. She has not harmed anyone. She has not injured herself. A judge does not like her behavior, so the woman has been deprived of her liberty and her rights under the Oregon and US constitutions. When a judge can arbitrarily put any person in a mental institution with no criminal conviction, no due process, and hold her there for a long time, society has lost its liberty. Government no longer has to put disfavored people on trial; it just has to declare them to be insane."
The Court of Appeals of the State of Oregon reversed the commitment order that allowed a judge in May 2002 to confine Webb to a psychiatric facility. Affirmed from the Bench — 1/29/04 — 191 Or App 654 State v. Webb, Terri Sue (A118326)
In Strange Days Indeed, a novel dealing with radical body acceptance and cruelty-free diet, author Stuart Ward lauds Webb for her bravery and dedication.
Footnote #31 in A Brief History of Nakedness By Phillip Carr-Gomm cites the Spring 2002 article on Terri Webb in Nude and Natural Vol. 21.3 'Beyond Safe Havens: Oregon's Terri Sue Webb' (see entry under Further Reading.)
Since 2007, Portland has hosted an annual daytime naked ride in June, as part of the Pedalpalooza bike festival. Portland's famously large naked ride, the World Naked Bike Ride, happens under the cover of night. For the last two years, the daytime ride has been in honor of Webb's work.