The Classy 'N Smart Stakes is a Thoroughbred horse race run annually in mid October at Woodbine Racetrack in Toronto, Ontario, Canada. An Ontario Sire Stakes, it is a restricted race for fillies and mares, age three and older. It is contested over a distance of one and one-sixteenth miles (8.5 furlongs) on Polytrack synthetic dirt and currently carries a purse of $94,913.

Inaugurated in 1997, the race was named to honor Sam-Son Farm's Champion filly and Canadian Horse Racing Hall of Fame inductee, Classy 'n Smart.

Speed record: (Through 1998, Woodbine times were recorded in fifths of a second. Since 1999 they are in hundredths of a second)

• 1:42.53 - Strut the Course (2014)

Most wins:

• 3 - Brass in Pocket (2002, 2003, 2004)

Most wins by an owner:

• 3 - Frank Di Giulio, Jr. (2002, 2003, 2004)

Most wins by a jockey:

• 3- Todd Kabel (2001, 2002, 2004)

Most wins by a trainer:

• 4 - Robert P. Tiller (2002, 2003, 2004, 2016)

• The Classy 'N Smart Stakes at Pedigree Query
• The 2008 Classy 'N Smart Stakes at Woodbine Entertainment^{[permanent dead link]}