Sherwood was born and raised in Idaho Falls, Idaho. She is the daughter of Don and Shirley Sherwood. She attended Idaho Falls High School located in Idaho Falls, Idaho.
Sherwood first started her pageant journey with the America’s National Teenager Scholarship Organization. She was crowned Miss Idaho National Teenager 1986. She then went on to represent Idaho at the 1986 America’s National Teenager pageant where she placed as third runner-up.
Afterwards, Sherwood went on to enter the 1989 Miss Idaho Teen USA pageant. In August of 1988, Sherwood was crowned Miss Idaho Teen USA 1989 on her first try at the title.
Sherwood then represented Idaho at the seventh annual Miss Teen USA pageant. There, she had an interview score of 8.688, a swimsuit score of 8.925 and an evening gown score of 8.850 making her average score 8.821. On July 25, 1989, Sherwood was crowned Miss Teen USA 1989 at the Orange Pavilion located in San Bernardino, California.
Sherwood later returned to the pageant stage in 1997, this time as a Miss contestant. She entered the 1997 Miss Idaho USA pageant. On her first try at the title, Sherwood was crowned Miss Idaho USA 1997, making her one of the first titleholders to hold a Teen and Miss USA state title.
Sherwood then went on to represent Idaho at the 1997 Miss USA pageant. There, she had an interview score of 8.63, a swimsuit score of 8.83 and an evening gown 9.19 giving her an average score of 8.88. On the final night of competition, Sherwood placed as first runner-up to Miss USA 1997, Brook Lee, of Hawaii.
Three months after the 1997 Miss USA pageant, Lee went on to win the title of Miss Universe 1997. As a result, Sherwood assumed the title of Miss USA 1997.
During her reign, Sherwood worked with Special Olympics. She also worked with the D.A.R.E. program and continues to volunteer her time speaking to students about resisting drugs and violence.
After crowning her successor, Sherwood married movie actor Dean Cochran. She also continued with her modeling career. She landed a role as a model on “The Price is Right” where she worked for a number of years.
On the show's February 13, 2009 broadcast, host Drew Carey announced that Sherwood and Cochran were expecting in the summer, with a scheduled due date of June 12, 2009. Sherwood took time off for the rest of Season 37 and into Season 38, as episodes begin taping in late May to early June 2009. On February 23, 2010, the show declined her request to be booked again on the show.
Sherwood filed a lawsuit against FremantleMedia in 2010 and won a reported $775,000 in November 2012 which later increased to over $8.5 million to include punitive damages.
On March 12, 2013, Sherwood was stripped of her lawsuit winnings when the trial court ordered that the case be reheard due to a recent state Supreme Court decision. Judge Kevin Brazile said that in February, two months after Sherwood declared victory, a state Supreme Court ruling affirmed the defense's argument that Brazile should have instructed the jury to determine whether pregnancy discrimination was a "substantial motivating factor" in the producers' decision. An undisclosed out of court settlement was reached in 2016.
Today, Sherwood still works as a model. She is also still married to Dean Cochran.