Born in Connecticut, Woodlock graduated from Yale College and worked as a journalist before attending Georgetown University Law Center.

After graduating, Woodlock was a lawyer in private practice at Goodwin, Procter & Hoar, and had stints at the U.S. Securities and Exchange Commission and U.S. Attorney's Office for the District of Massachusetts.

Appointed to the federal bench in 1986, Woodlock presided over a number of noteworthy cases and was a key figure in the construction of the John Joseph Moakley United States Courthouse on the Boston waterfront.

In his ruling, Woodlock wrote: "Gramajo was aware of and supported widespread acts of brutality committed under his command resulting in thousands of civilian deaths.

"[14][15] In 2008, Woodlock presided over a case involving the Massachusetts Bay Transportation Authority (MBTA), in which he issued an injunction barring three students at the Massachusetts Institute of Technology from disclosing security vulnerabilities in the MBTA's CharlieCard system; the decision was controversial, and resulting press attention resulted in further publicity of the security lapse.

[10] Woodlock was the judge who presided over litigation between the South Middlesex Opportunity Council, an anti-poverty group, and the Town of Framingham and its officials.

[18] In 2020, Woodlock issued a preliminary order directing the Commonwealth of Massachusetts to allow gun stores (but not shooting ranges) to reopen, overruling Governor Charlie Baker's executive order to the extent it excluded gun retailers from a list of essential retailers permitted to remain open during the coronavirus pandemic.

[20] In 2010, Woodlock sentenced computer hacker Albert Gonzalez to 20 years and one day in prison,[21] after Gonzalez pleaded guilty the previous year to hacking Heartland Payment Systems' corporate computer system as part of a scheme to steal millions of payment card numbers.

[25] In 2012, Woodlock sentenced Catherine E. Greig, the longtime companion of Boston organized crime figure James "Whitey" Bulger, to eight years in jail.

[27] In 2014, Woodlock oversaw the criminal proceedings against two friends of Boston Marathon bomber Dzhokhar Tsarnaev, who were convicted of obstruction of justice for destroying evidence and lying to authorities who were investigating the crime.

[7] In 2019, Woodlock was the judge assigned to the criminal case against Jeffrey Bizzack, a California businessman who was one of many parents charged in the Varsity Blues admissions bribery scandal.