The Winterfolk Story

Twenty-Five Years of Artists, Audiences, Songs and a Festival Nobody Had Planned

 

A Place to Gather

By the early years, something else was becoming apparent.

Winterfolk wasn’t simply presenting a series of concerts.

A community was gathering around them.

Toronto already had strong folk, roots and blues communities. Winterfolk didn’t invent any of those, nor would it be sensible to claim it did. What the festival provided was a place where those overlapping communities could gather at the same time.

Musicians saw their peers. Audiences encountered artists they already knew and discovered others they didn’t. Presenters met performers. Artists met other artists. Fans met each other.

Older musicians encountered younger musicians. Younger musicians found themselves sharing stages with people who had been doing it for decades.

Nobody called it connecting generations.

They were too busy doing it.

For one weekend in the middle of winter, a considerable portion of the music community was in the same place.

That became one of Winterfolk’s most important functions.

It also created paid work during a part of the year when festival work was scarce.

The word paid matters.

Winterfolk has always put a value on an artist’s time, talent and work. From the beginning, Gladstone’s view was uncomplicated: if a festival sells tickets to hear musicians perform, asking those musicians to work for nothing seems a rather peculiar interpretation of the music business.

Artists at Winterfolk are paid.

The amount available has varied with the festival’s finances, and Winterfolk has never pretended to possess unlimited resources.

The principle is considerably simpler than the accounting:

Treat artists properly. Pay them as well as circumstances allow. Try to make sure they leave wanting to come back.

Happy artists make a great festival.

Getting Inside the Music

Winterfolk discovered early that a festival could do more than put musicians on stages and ask them to play songs.

Workshops became an important part of the experience.

A concert tells an audience what an artist created.

A good workshop can reveal why.

Songwriters talk about where words come from, how songs are assembled, how personal experience becomes material, and how politics, social injustice, relationships and events in the world find their way into music.

Then the audience starts asking questions.

Often, that is where things become interesting.

At first, Winterfolk assigned artists to workshop topics it thought would suit them. It soon discovered a better source of workshop ideas:

The artists.

Artists began proposing subjects and bringing together performers with shared interests, experiences or stories.

When artists own the idea, they tend to own the room as well.

One workshop captures the concept particularly well. Two artists divide the audience into two groups. Each artist then has 45 minutes to help half the room write a song.

At the end, two songs that didn’t exist three-quarters of an hour earlier are performed by the people who just wrote them.

Part concert. Part songwriting lesson. Part controlled musical accident.

Engage. Educate. Entertain.

The workshops also did something less obvious.

Experienced songwriters shared what they knew. Younger artists brought their own ideas. Audiences became part of the process. People who might never have spoken to each other outside the festival suddenly had a song to talk about.

Music moved around the room.

So did experience.

Connecting generations had begun to become part of what Winterfolk did, even though nobody had given it a name yet.

Growing Into Toronto

As Winterfolk grew, it demonstrated how well an urban festival could work when venues, restaurants, transit and audiences were concentrated within a walkable area.

During the Danforth years, audiences increased and the festival became better known. People came because they had heard about Winterfolk. Others discovered it simply because it was happening around them.

The effect extended beyond the festival rooms. Audiences ate, drank and spent money in surrounding businesses during what would otherwise be a February weekend in Toronto.

February, it turns out, has certain commercial disadvantages.

Toronto was particularly well suited to the Winterfolk idea. It had musicians, audiences, clubs, neighbourhoods and public transportation. Winterfolk deliberately located itself near subway stations so audiences could move through the city without needing a car.

But the environment surrounding live music did not stand still.

Listening habits changed. Streaming arrived. Other forms of entertainment competed for attention. The old habit of regularly going to a small club specifically to hear live music weakened.

The consequences eventually became visible in the venues themselves.

Rooms closed. Others changed. The economics changed. Winterfolk had fewer suitable places in which to operate.

So Winterfolk adapted.

It would not be the last time.

The Tranzac Club eventually became Winterfolk’s most consistent venue and a particularly compatible home. Its intimate rooms also reinforced something that had been part of Winterfolk from the beginning.

Proximity matters.

Big Names in Small Rooms

Winterfolk sometimes describes the experience as big names in small rooms.

Many performances feel closer to hearing somebody play in a living room than watching a conventional festival stage.

Artists sit in the audience watching other artists. They walk down the hall, have something at the bar, participate in workshops and talk to people.

There isn’t much distance between performer and audience.

And there isn’t much distance between generations either.

An established artist may finish a set and sit down to watch somebody just starting out. A young songwriter may find themselves talking to somebody whose records they grew up hearing. An audience member who came to see a familiar performer may spend the next 45 minutes listening to somebody half their age.

No special program is required.

Put people in the same room and occasionally something useful happens.

Winterfolk has always mixed established performers with artists still building careers.

It doesn’t claim credit for what happens afterward.

It provides the room.

Winterfolk does not operate a formal mentorship program and doesn’t presume to tell songwriters how to make their music. What it can provide is a professional stage and some practical guidance about how that stage works: start on time, finish on time, communicate with the audience, understand the festival structure and walk onto the stage believing you belong there.

Then let the artist be the artist.

One of the pleasures of Winterfolk is seeing somebody before everybody knows who they are.

People come to see artists they already know.

They may also see the music icons of the future.

Someday, somebody may be able to say:

“I saw them in a small room at Winterfolk.”

The Music Changes, but It’s Still the Same

Each generation writes about the world it inherits.

Politics change. Social issues change. Relationships change. Technology changes. The things people worry about, celebrate, argue about and hope to fix change.

Eventually somebody writes a song about it.

Folk, roots and blues have always overlapped at Winterfolk. Trying to draw exact boundaries between them is usually an excellent way to start an argument and a poor way to spend an afternoon.

Blues has been integral from the beginning, reflecting Toronto’s strong blues community.

The blues is here forever.

The subjects change.

The language changes.

The musicians change.

Music has changed, but it’s still the same.

That contradiction makes considerably more sense once you’ve listened to enough songs.

A song written today may sound nothing like one written 50 years ago. The person writing it may be worrying about a completely different world.

But somebody is still sitting down, trying to put that world into words and music.

Then somebody else listens.

That is how music travels between generations.

It always has.

Connecting Generations Through Music

Winterfolk’s original core audience included many people who came of age during the folk revolutions of the 1960s, ’70s and ’80s. They returned year after year. Some became so familiar that the festival team knew them by name.

That generation is aging.

There is nothing particularly mysterious about that.

People change. Audiences change. Music changes.

Winterfolk tries to change with them.

Supporting young and emerging performers has been part of Winterfolk from the beginning, but in recent years that emphasis has increased considerably.

The objective isn’t to discard one generation and replace it with another.

It is to get them into the same rooms.

There is something satisfying about watching a longtime Winterfolk audience member listening intently to a performer young enough to belong to another generation entirely.

An established artist may be sitting in the audience watching somebody at the beginning of a career. A younger songwriter may find themselves in a workshop beside somebody who has been writing songs for 40 years.

And both may learn something.

That’s when you know it’s working.

In 2026, Winterfolk finally found words for something it had been doing for years:

Connecting Generations Through Music.

The phrase is new.

The idea isn’t.

It was there at the first Winterfolk when a 17-year-old singer from Peterborough shared a festival with established performers.

It was there when workshops put experienced songwriters, emerging artists and audiences into the same conversation.

It was there when longtime Winterfolk audiences began discovering artists from another generation.

And it will be there as the next generation arrives.

The slogan didn’t create the philosophy.

It finally gave it a name.

Keeping the Thing Running

Winterfolk is a not-for-profit, volunteer-driven organization with no full-time staff.

A small organizing team puts the festival together. Contractors and technical personnel are hired where required. A large volunteer crew helps turn the plan into an actual festival.

Many volunteers return year after year.

They are the workhorse of Winterfolk.

Without the community and without the volunteers, there would be no Winterfolk.

That isn’t ceremonial language put into an annual report.

It is an operating fact.

The volunteers themselves are another connection between generations. Some have been around for years. Others are new. Knowledge gets passed along because somebody who knows how something works shows somebody who doesn’t.

Not everything requires a training manual.

Winterfolk itself has largely been learned the same way: one year at a time.

Do something. See whether it works. If it doesn’t, fix it. If it does, remember what you did.

The method lacks glamour but has produced surprisingly durable results.

There have been lean years. Grants can be unpredictable, sometimes leaving the festival uncertain of its final operating budget until relatively close to the event.

Winterfolk watches expenses carefully and adjusts what it does to the resources available.

Money isn’t a dirty word in the arts.

Running out of it is.

There have been other complications.

On one occasion, Winterfolk unexpectedly lost a venue during the festival. A substantial portion of the schedule suddenly had nowhere to go. Sets were shortened, artists were combined, schedules were changed and performances moved until everybody had somewhere to play.

It wasn’t the schedule anyone had planned.

It was, however, a schedule.

Then came COVID.

Winterfolk could not operate normally, so it found another way.

Artists were filmed and interviewed, performances went online, and some live music continued under severe attendance restrictions.

At times, only a handful of people could be in a room.

Winterfolk still presented a festival.

Then, after more than two decades of deliberately staging a festival in Toronto in February, Winterfolk finally encountered a serious blizzard during festival weekend.

Apparently this possibility had been overlooked.

Attendance dropped.

The shows continued.

People still came.

They had fun anyway.

Winterfolk has not spent 25 years lurching from crisis to crisis.

Most things go right.

That is generally what planning is for.

SECTION HEADER: Everything Is Exactly the Same Except Different

The larger challenge has always been keeping pace with a moving target.

Ticketing changed. Promotion changed. Technology changed. Listening habits changed. Venues disappeared. Audiences changed. New artists arrived.

The basic job remained remarkably familiar.

Find good artists. Put them in good rooms. Bring in an audience. Run the stages properly. Pay people. Keep expenses within available revenues. Watch what is happening in the music community. Pay attention to who is emerging and what audiences are responding to.

Then do it again next February.

Everything is exactly the same except different.

Perhaps that explains some of Winterfolk’s longevity.

Festivals are easy to start and considerably harder to keep.

Winterfolk began as an experiment in 2003 and enters its 25th edition in 2027.

It has never been particularly interested in becoming enormous.

Keep what works. Change what doesn’t. And don’t make it bigger just so somebody can say it’s bigger.

Winterfolk grew out of Toronto—its musicians, audiences, clubs and winters. It isn’t designed to be mass-produced or exported from city to city.

There is some irony in what happened along the way.

Winterfolk began because there was no obvious model to follow.

Eventually, other festival organizers began asking Winterfolk how its model worked.

Not bad for something that started because a musician couldn’t get booked into somebody else’s festival.

The Next Generation

As Winterfolk enters its 25th edition, another generation is beginning within the organization itself.

After 25 years, Brian Gladstone is preparing to hand the festival director’s role to a new director while remaining available as a mentor during the transition.

That seems particularly appropriate for a festival now described by the words Connecting Generations Through Music.

The idea applies offstage too.

One generation learns something.

Then it passes it along.

Nobody knows what folk, roots or blues will look like ten years from now.

There will be new artists, new technology, new musical styles and new problems nobody has thought of yet.

Some current trends will disappear and eventually return with a new name.

Winterfolk will try to change with them.

Mostly, it will keep on keeping on.

SECTION HEADER: A Place to Gather

Underneath everything else, the idea remains remarkably simple.

Winterfolk didn’t create folk, roots or blues music.

It didn’t create Toronto’s musicians, and it didn’t create their audiences.

It created a place for them to gather.

A place where an established artist can sit in the audience watching somebody just beginning.

Where a songwriter can explain where a song came from.

Where an audience can help write one.

Where somebody who grew up with the folk music of the 1960s can discover somebody writing songs about the world today.

Where a young performer can stand on the same stage that another generation stood on before them.

Where somebody can discover a future music icon in a small room and years later say:

“I saw them at Winterfolk.”

The phrase came 24 years after the idea.

It had been happening all along.

Connecting Generations Through Music.

At the end of a Winterfolk night, people walk out still talking about what they heard.

“Wasn’t that great?”

“Did you see…?”

Somebody came to hear one artist and is leaving talking about another.

Rarely does somebody leave Winterfolk without a smile.

After 25 years, that’s not a bad measure of success.