1. VANITY FAIR PORTRAITS: PHOTOGRAPHS 1913–2008
This exhibit of 146 portraits from the magazine’s archives represents 95 years of history with images of momentous events, cultural icons and celebrities, including Amelia Earhart, Cary Grant and firefighters at Ground Zero immediately following 9/11. This is the last stop (and only Canadian showing) on the exhibit’s world tour; look for work by big-name photographers, including Helmut Newton, Mario Testino and Annie Leibovitz. Sept. 26 to Jan. 3, 2010. $22. Royal Ontario Museum, 100 Queen’s Park, 416-586-5524, rom.on.ca.

2. THE WORD ON THE STREET FESTIVAL (FREE!)
Literary lovers across the country are united by this annual festival, now in its 20th year, which hosts versions in Vancouver, Kitchener, Halifax and Toronto. Presentations, workshops and meet and greets are all on the agenda, but we’re also looking forward to cooking demos (with samples) at the new Cooks ’n’ Books stage. Sept. 27. Queen’s Park, 416-556-0812, thewordonthestreet.ca.

3. PARKDALE FOOD, EARTH AND CULTURE FESTIVAL (FREE!)
This afternoon event celebrates the environment with locavore-friendly snacks ($2 per plate) from neighbourhood restaurants and bike tune-ups. Also on the bill: kid-friendly games, live performances by the African drumming troupe Baro Dununba and local rapper The Voyce, and shiatsu massages. Sept. 27. Masaryk Park, 220 Cowan Ave., 647-438-0038, greenestcity.ca/whats-on.

4. THEY SHOOT VIDEOS, DON’T THEY? (FREE!)
Elevating the humble music video to an art form, local filmmaker and director Scott Cudmore curates this screening series at the 107 Shaw gallery. Videos can be viewed on the big screen or on monitors throughout the gallery. Sept. 25. 107 Shaw St., 1zero7.com.

5. THE CLOTHING SHOW
Deeply discounted designer threads are the main draw at this twice-yearly fashion event, but the indie designers and new green-themed section are close runners-up. Don’t miss the runway shows, the gallery featuring up-and-coming local designers or the swag, this time a selection of product samples handed out in an eco-friendly bag designed by Niagara-on-the-Lake’s Pause Designs. Sept. 25 to 27. $10. The Better Living Centre, Exhibition Place, 195 Princes Blvd., theclothingshow.com.

6. SECRETS OF A BLACK BOY
This no-holds-barred look at being black and male in Toronto is being hailed as the boy’s-eye view of issues raised in Trey Anthony’s 2005 smash ’Da Kink in My Hair, including interracial love, sexuality, abuse and violence. It’s a fitting comparison; Anthony is the executive producer and dramaturge of the play, which was written by her little brother, Darren. Sept. 25 to Oct. 3. $28–$68. The Music Hall, 147 Danforth Ave., 416-778-8163, secretsofablackboy.com.

7. KOERNER HALL GRAND OPENING
The city’s classical music aficionados have been eagerly anticipating the grand opening of Koerner Hall at the Royal Conservatory for eight years. This gala celebration will be the public’s first chance to experience a performance in the 1,135-seat space. Pianist Anton Kuerti, the Toronto Mendelssohn Choir, and vocalists Erin Wall, Wallis Giunta, Colin Ainsworth and Robert Pomakov join the Conservatory’s orchestra. Sept. 25. $100–$250. Koerner Hall, The Royal Conservatory, 273 Bloor St. W., 416-408-2824, rcmusic.ca.

8. BOOK-MOVIE-MUSIC SWAP MEET
This culture-rich swap meet is a wallet-friendly way to update the library, DVD collection or CD tower. Organizers recommend bringing at least three items, each of which can be traded for another item. There are no rules about what can be traded for what, so DVDs can be exchanged for books or CDs. Just be sure to choose wisely, because all swaps are final. Sept. 26. $5. Walmer Road Baptist Church, South Entrance, 188 Lowther Ave., swapsity.ca.