[2] Each year of programming is connected to a broader theme and covers a wide variety of topics in the arts, politics and society, and science and technology.

Under Eileen Mackevich's leadership, by 2006, the independent Festival had expanded to nearly 150 programs over 16 days, in more than 30 venues, involving nearly 40 partner institutions and several hundred site volunteers, and attracting a combined audience of nearly 50,000.

Notable Presenters: Alan Lightman, Harold Ramis, Alison Lurie CHF XII: Words & Pictures (2001) Notable Presenters: Leonard Nimoy, Jonathan Franzen, Witold Rybczynski, Junot Díaz, Art Spiegelman CHF XIII: Brains & Beauty (2002) Notable Presenters: Francis Fukuyama, Joyce Carol Oates, Jeffrey Eugenides, Francine Prose, Mira Nair CHF XIV: Saving + Spending (2003) Notable Presenters: Roberto Benigni, Oscar Hijuelos, Tom Wolfe CHF XV: Time (2004) Notable Presenters: August Wilson, Maxine Hong Kingston, Clive Barker CHF XVI: Home and Away (2005) Notable Presenters: Margaret Atwood, Salman Rushdie, Annie Proulx, Susan Orlean CHF XVII: Peace and War (2006) Notable Presenters: Paul Krugman, Azar Nafisi, Joel Meyerowitz, Frank McCourt, Joan Baez, Errol Morris, Wesley Clark, Garry Trudeau CHF XVIII: The Climate of Concern (2007) Notable presenters: Wangari Maathai, E.L. Doctorow, Philip Pullman, Majora Carter, Peter Singer, Roger Payne, Terry Tempest Williams, W.S.

Merwin, Edward Burtynsky, Maya Lin, Dave Eggers, Colin Quinn, Cat Chow, Greil Marcus, Amartya Sen, and the head writers of The Onion CHF XIX: Thinking Big!

Collins, Kay Ryan, Tim Reid, Tom Dreesen, Ian Frazier, John Adams (composer) CHFXXI: The Body (2010) Notable presenters: Kareem Abdul-Jabbar, Sam Shepard, Dan Savage, Sarah Jones (stage actress), Sherwin B. Nuland, Laura Kipnis, Frank Shorter, Alpana Singh CHF XXII: tech•knowledgē (2011) Notable presenters: Stephen Sondheim, Jonathan Franzen, Jeanne Gang, William Gibson, Michael Taussig, Cathy Davidson, Yuri Lane, Claudia Rankine, Jared Diamond CHF XXIII: America (2012) Notable presenters: Camille Paglia, Mark Helprin, Charles C. Mann, John Lewis Gaddis, Yves Béhar, Austan Goolsbee, Neil MacGregor, Nate Silver, Ian Frazier, Russ Feingold, David Brooks, Elie Wiesel, Richard Ford CHF: Animal - What Makes Us Human (2013) Notable presenters: David Axelrod, Rick Bayless, Jonathan Safran Foer, Kimberly Peirce, Martina Navratilova, Sherman Alexie[10] CHF: Journeys (2014) Notable presenters: Anne Rice, Andrew Ross Sorkin, Cheryl Strayed, eighth blackbird[11] CHF: Citizens (2015) Notable presenters: Ta-Nehisi Coates, Elvis Costello, Lawrence Lessig, Bob Mankoff[12] CHF: Speed (2016) Notable presenters: Gloria Steinem, Trevor Noah, Thomas Friedman[13] CHF: Belief (2017) Notable presenters: Al Gore, Reza Aslan, Samantha Power[14] CHF: Graphic (2018)[15][16] Notable presenters: Tom Hanks, Abbi Jacobson, Hanif Abdurraqib, Ron Chernow, Jill Lepore, Tim Wu, Phoebe Robinson, Doris Kearns Goodwin[17] CHF: Power (2019) Notable presenters: Nikki Giovanni, Julia Louis-Dreyfus, Henry Louis Gates, Jr., David Brooks, Stacey Abrams, Raghuram Rajan[18] CHF: Vision (2020) Notable presenters: Tori Amos, Abby McEnany, Margaret Atwood, David Axelrod, Maria Hinojosa, John Dickerson[19]