[2][3][4] Weekes attended Bishop Anstey High School, the University of the West Indies, Cave Hill, from which she graduated with a Bachelor of Laws degree, and the Hugh Wooding Law School; she was called to the Bar in 1982.

[5][6] After graduation she worked in the office of the Director of Public Prosecutions for 11 years, before going into private practice in 1993.

[6] In September 2016 Weekes was appointed to the appeals court in the Turks and Caicos.

[8] On 5 January 2018, Weekes, then a judge of the Turks and Caicos Islands Court of Appeal, was put forward as a presidential candidate by the People's National Movement government of Prime Minister Keith Rowley in hopes of reaching a consensus with the United National Congress-led parliamentary opposition of Kamla Persad-Bissessar, which later endorsed her nomination.

[9] In 2023, United Nations Secretary General António Guterres appointed Weekes as co-chair of the United Nations High-Level Panel on the Teaching Profession, alongside Kersti Kaljulaid.