May Bailey is the domineering matriarch of the Bailey family. Her strong will and convictions have led her family through tough times, but have also served to alienate her from her children and grandchildren. May wants nothing more than for her grandson Hubert to take over the family’s mining business and carry on what she and her husband began. Throughout the series, May evolves from a strict and rigid figure into a more lenient leader, learning to let the past go and embrace the present.

Shirley Douglas is a cherished Canadian icon both on and off screen. Her role as May Bailey in Wind at My Back was Douglas’ primetime series debut. She has also appeared in an episode of Road to Avonlea, where she played the head of an all girls school. Douglas has starred in many films such as Stanley Kubrick’s Lolita, Dead Ringers, Shadow Dancing, and Mesmer. Douglas has also performed in theatre, playing Big Mama in a Stratford production of Cat On A Hot Tin Roof and Hagar in the National Arts Centre production of The Stone Angel.

Grace Bailey may often come across as naïve, but her can-do attitude outweighs any dream-like qualities. Above everything, Grace longs to forge her own path in life and be seen as a confident, independent woman by her family. To increase her independence she begins to work at the New Bedford radio station CRNB. Grace is often the shoulder her nephews can lean on to help them get through the hurdles life throws at them.

Kathryn Greenwood has had many roles over the years in both TV and film. Greenwood has been in the TV shows Street Legal, Goosebumps, History Bites, and The Drew Carey Show. She has been in many comedic roles in Royal Canadian Air Farce, This Hour Has 22 Minutes, and Who’s Line Is It Anyway. She has been in films including: Kids in the Hall: Brain Candy, and The Man. She has also done voice work for the animated movie Anne: Journey to Green Gables and the TV show The Dating Guy.

Hubert (Hub) Bailey is the practical, level headed son of Honey Bailey- Sutton. As the eldest child, Hub knows that when his father dies he must step up to help take responsibility with his mother and siblings. Though he faces many emotional battles through the series, Hub rises above the challenges and grows into a well rounded, warm hearted individual with a strong sense of justice. He often does what he thinks is right-even if not everyone agrees with him.

Dylan Provencher has appeared in the TV series Goosebumps and Are You Afraid Of The Dark, as well as TV movies such as, The Sweetest Gift, Earthquake in New York, and Mail to the Chief. His last role was in the TV movie Ta Voix Dans la Nuit in 2002. Provencher currently works in real estate.

Henry (Fat) Bailey is a dreamer who often feels as if his family doesn’t take him seriously. Kind hearted and imaginative, Fat can often find himself getting into situations that don’t always end well for him. He looks up to his brother Hub, but feels like he will never measure up to him in their family’s eyes. Fat dreams of adventure and hopes to forge an exciting life for himself away from New Bedford.

Tyrone Savage’s first acting credit was as Fat Bailey in Wind at My Back. Both of his parents, Janet-Laine Green and Booth Savage, are also involved in the Canadian film and TV industry. Savage has appeared in the TV shows Goosebumps, Are you Afraid of the Dark, Stoked, Instant Star, and Reign to name a few. He has also done voice work for Redwall, Total Drama Island and Total Drama All Stars. Savage has appeared in numerous Stratford festival plays and is a founding member of Red One Theatre Collective.

Max Sutton is the good-natured school teacher and aspiring author who falls for Honey Bailey. He is the father of Zack Sutton and the step-father of Honey’s three children: Hubert, Henry and Violet. Max is the backbone of the Bailey-Sutton family, proving time and time again that family is more than just blood. Throughout the series, Max explores what it means to be a father, a teacher, and what it means to achieve your dreams.

James Carroll appeared in a few Sullivan Entertainment programs, including Under The Piano and Anne of Green Gables: A New Beginning, as well as in many plays, such as Guys and Dolls, Midsummer Night’s Dream, Gunmetal Blues, and Company. Carroll was also in numerous TV shows like Street Legal, The Gathering, and Top Cops. For six years Carroll hosted a popular Muskoka radio show for Hunter’s Bay Radio. Sadly, Carroll passed away in 2016 at the age of 60.

Toppy starts the series as a snobbish, spoiled wife, but soon comes into her own and finds her own strength when she and her husband Bob Bailey divorce. Toppy is creative, with a flair for the dramatic that is unrivaled. She establishes herself as a respected business woman and later as an author and becomes someone the rest of the Bailey’s can rely on in time of turmoil. Her one great wish in life is to have a better relationship with her daughter, Doris, who seems to want nothing to do with her mother once she starts creating a life for herself outside of her failing marriage.

Robin Craig has been in numerous Shaw Festival productions and also appeared in the Academy Award nominated short, Life Times Nine and in the film The Power of Three. As well, Craig has been in TV shows like Street Legal, The Campbells, and Degrassi: The Next Generation. She won a Gemini for her role as Toppy Bailey in Wind at my Back.

Honey Bailey-Sutton’s kindness is only matched by her resilience. After the tragic death of her husband Jack, she must do everything in her power to keep her three children: Hubert, Henry and Violet, from her mother in law, May Bailey. Through everything that life throws her way, Honey tries to stay optimistic and rely on the love of her family, including her new husband Max Sutton, to get through the most difficult time in Canadian history, the Great Depression.

Laura Bruneau played Honey Bailey-Sutton after Cynthia Belliveau left Wind At My Back to pursue other interests. Before Bruneau took the role of Honey, she was in TV shows like The Beachcombers, Bare Essence, Knight Rider, Katts and Dog, Street Legal, Material World, and The Outer Limits. She was also in the TV movies Packin’ It In and Sealed with a Kiss. She can also be seen in the movie Little Ghost. Bruneau has appeared in stage productions of The Rocky Horror Picture Show, and Hot and Cold.

Honey Bailey-Sutton’s kindness is only matched by her resilience. After the tragic death of her husband Jack, she must do everything in her power to keep her three children: Hubert, Henry and Violet, from her mother in law, May Bailey. Through everything that life throws her way, Honey tries to stay optimistic and rely on the love of her family, including her new husband Max Sutton, to get through the most difficult time in Canadian history, the Great Depression.

Cynthia Belliveau began the series as Honey Bailey, before leaving Wind at My Back in 1999 to star in the TV series Caitlin’s Way, where she had the role of Dori Lowe. Caitlin’s way was Belliveau’s last TV credit. Belliveau was also in episodes of TV shows like Alfred Hitchcock Presents and Goosebumps. She played Sally Rand in the TV movie Million Dollar Babies. Her role as a reporter in E.N.G. won her a Gemini nomination in 1995.

Maisey McGinty starts her time in new Bedford with a splash, but she soon becomes an inseparable friend to Hub and Fat. The granddaughter of May Bailey’s old friend Leo, Maisey is always coming up with new schemes and often drags Fat along with her to disastrous and hilarious ends. Through the series, Maisey matures from a tough tomboy into a well rounded, thoughtful, and talented young woman.

Dalene Irvine has appeared in the TV show Goosebumps, as well as Sullivan Entertainment productions Anne of Green Gables: A Continuing Story, Anne: Journey to Green Gables, and Anne of Green Gables The Animated Series where she was the voice of Felicity King. She was also in the popular children’s movie Cadet Kelly, which starred Hilary Duff.

Ollie Jefferson is the town mechanic, with a huge crush on Grace Bailey. He is hardworking, but also a dreamer at heart and highly romantic. When things don’t work out with Grace, he marries Margery and they adopt a baby boy. Throughout the series, Ollie is a dependable figure who is often eager to help others.

Crone has been in many TV shows over the years, including The Red Green Show, Eerie Indiana, Goosebumps, Monk, Susan Thomas F.B.Eye, Doc, Murdoch Mysteries and The Good Witch. He had a role on the CBC program Little Mosque on the Prairie as the character Fred Tupper. He has done voice work for animated shows like Odd Job Jack, Bob and Doug, and The Dating Guy. He has also been in a few movies, such as Pushing Tin, Bait, The Recruit, New York Minute, and Hairspray.

Bob Bailey is the hard-working, oldest son of May Bailey. Bob feels that he must live up to all the expectations his parents put on him growing up, and as such, doesn’t let on that the family’s mining business is in trouble until it's too late. Disgraced with his failures and divorce, Bob moves away to pursue other interests.

Dan Lett, a music and theatre graduate from La Salle University and Villanova University, has had a few roles in Sullivan Entertainment films, such as Butterbox Babies, Under The Piano, and Anne of Green Gables: The Continuing Story. He won three Gemini Awards for his work in the program Made In Canada. He has had extensive TV work in programs like Murdoch Mysteries, Flashpoint, Dan For Mayor, and Lost Girl. He has appeared in films like The Shape of water, Molly’s Game and X-men Apocalypse.

Del Sutton is the older brother of Max Sutton and leads the life of a drifter, moving from place to place. He settles in New Bedford for a time, working as a mechanic and starting a relationship with Grace Bailey, but ultimately feels that he needs to move on and try and better his life. Often lighthearted, Del approaches life with a sense of amusement that is not always appreciated by his younger brother Max.

Ron Lea has been in numerous TV shows with roles in Canadian productions like E.N.G, Street Legal, Due South, Goosebumps, This Is Wonderland, Jeff Ltd., and Flashpoint. He has been in American programs including Susan Thomas F.B. Eye, Supernatural, and Smallville. His movie roles have been in Iron Eagle IV, The Recruit, Saw IV, and Bon Cop Bad Cop.

After the tragic passing of his wife, Jim Flett and his son Pritchard move to New Bedford where he takes on the role of teacher. Jim develops feelings for Grace Bailey, but is afraid to pursue them. Soft spoken, but highly intelligent, Jim struggles to find the best way to move forward with his life and raise his son without his wife.

Robert Bockstael started his career with a lot of voice work for animated TV shows, such as Dennis The Menace, Babar, Rupert, X-Men and Sailor Moon. His other TV roles include spots on the TV shows Street Legal, Nikita, The Famous Jett Jackson, Doc, Flashpoint, and Delilah & Julius. He is perhaps best known for his role as Brian Fletcher on North Of 60. He can also be seen in the Sullivan Entertainment program Anne of Green Gables: A New Beginning.

Archie Attenborough is the shy town drugstore owner who becomes smitten with Toppy Bailey. A leader in the New Bedford community, Archie was a staunch supporter of Max Sutton and his bid for mayor. Like Toppy, Archie has a flair for the dramatic and involves himself with plays that are put on for the town’s benefit.

Blackburn has had many roles throughout his career in TV shows and movies. His TV show credits include Street Legal, Susan Thomas: F.B.Eye, Zoe Busiek: Wild Card, Doc, Little Mosque on the Prairie, Heartland, Flashpoint, The Border, and Lost Girl. He has been in other Sullivan Entertainment programs like Road To Avonlea, Under The Piano, and Sleeping Dogs Lie. He has also had parts in the movies Murder at 1600, Loser, and Blue State.

Doris is the snobbish and opinionated daughter of Bob and Toppy Bailey. Because she grew up in an affluent family, she holds herself above her cousins and often looks down on the rest of her family-including her mother, Toppy, after she divorces her father. She holds her father in the highest regard and once she goes away to an all girls school, she cuts all ties with her family in New Bedford, preferring to spend time with him and her new influential friends from school.

Kathryn Long is a very talented dancer and singer. She won the Showstopper American Dance Championships and was a finalist in YTV’s Vocal Spotlight Talent Search. She can be seen in other TV shows, including Road To Avonlea, Goosebumps, Ready Or Not, and Are You Afraid Of The Dark, and the TV movie Degas and the Dancer.