Olson was born Anna Tomcik in Atlanta, Georgia. Her parents, Donna and Andy Tomcik emigrated to Toronto where she grew up. Olson's grandparents came from Slovakia. Olson earned a degree in political studies and sociology from Queen’s University in Kingston. She also worked for a time in a bank in downtown Toronto. During her lunch breaks, Olson wandered the St. Lawrence Market searching for different ingredients and inspiration for her next dinner party. Olson then enrolled in the College of Culinary Arts at Johnson & Wales University in Denver, Colorado. Upon her graduation from the university, Olson traveled across the United States. She would eventually find her way to Niagara Falls. Olson was a pastry chef at Inn on the Twenty in Jordan, Ontario for seven years, where she met her husband, chef Michael Olson.
Olson's writings include The Inn on the Twenty Cookbook, co-authored by her husband and published in 2000. Olson also published a cookbook called Sugar in 2004. It was a companion to her TV show by the same name which can be found on Food Network Canada. Olson co-authored another book with her husband which was released in October 2005. The book is called Anna & Michael Olson Cook at Home: Recipes for Everyday and Every Occasion. This is a menu-driven book which highlights how Olson and her husband cook at home. It also includes tips and tricks for entertaining and weeknight dining. In late 2006, another cookbook with recipes derived from "Sugar", called Another Cup of Sugar was released. Olson also writes for publications such as Vines and LCBO Food and Drink.
Anna Olson opened Olson Food at Port in Port Dalhousie, a historic lakeside community in St. Catharines, Ontario. She sold the Port Dalhousie shop in April 2009, to their long-time friend and pastry chef Andrea Poirier and her sister Leesa Leshkewich.
In July 2008, the Olsons opened their second location, Olson Foods at Ravine, in partnership with Ravine Vineyards in St. David's, Ontario. It was announced in a press release dated Feb 1, 2010 that they are no longer involved with the location at The Ravine Winery and the partnership was ended.
Olson supports a local program called the Niagara Women’s Enterprise Centre. The centre provides training in the hospitality sector to women who might not have that opportunity, with her end-of-the-day product given to a local YWCA women's shelter or Out of the Cold Program.
Olson has been featured for the past few years in various promotions for Starbucks Coffee Canada. This started in the winter of 2004, when her Mocha Bites recipe was featured on a recipe card available in Starbucks retail stores.
In the spring of 2005, Starbucks Coffee featured Olson in television advertisements aired nationally to promote their sweepstakes that was held in-conjunction with Food Network Canada and to introduce Anna's Brown Sugar Pound Cake being sold in retail stores. This also included in-store advertising of her cake with special pastry toppers and take-home recipe cards.
In winter 2005, her Chai Decadence Chocolate Bundt Cake was one of the featured holiday pastries sold in stores (once again promoted with in-store recipe cards). Olson was also featured in the Christmas television advertisement for Starbucks Coffee Canada. In the spring of 2006, Olson appeared in television advertisements promoting Starbucks Coffee's annual Brewing Sale 2006.
Starting in late 2005, Olson has appeared in television advertisements for Splenda and has provided recipes on their official Canadian website.
Olson has appeared in television advertisements for KitchenAid appliances.
Olson did commercials for Pillsbury Christmas cookies during the 2006 Christmas season.
Olson's "Chef's Selections" appears in Bulk Barn's flyers and website.
Olson did television commercials and flyer ads in 2010 for Home Hardware, advertising kitchen products and appliances. She also has a recipe section on the Home Hardware website and contributes to Home Hardware's free quarterly magazine "Home at Home".