top of page

Awards & Nominations:

2019 - Hamilton Fringe Festival  : Winner:

Audience Choice Award  : "Diamond in the Rough"

2019 - Hamilton Spectator :Readers Choice : Nominee  : Best Live Theatre : Chasing Shadows Productions 

2017 -Hamilton Fringe Festival : Winner: Best of Venue : Hamilton Theatre Incorporated "Swingin' in St. John's"

2016 - Hamilton Music Awards : Nominee : Contemporary Folk Recording : "Chasing Shadows"

2008 - Sudbury's Musical PlaygroundGrand Prize Winner (Best Children's Song) : "Swords & Dinosaurs"

Will Gillespie is a singer-songwriter, musician and entertainer from Hamilton, Ontario, Canada.


The classic Canadian finger-pickin' Folk troubadour, another unique, original Artist performing his own songs, in his own snazzy, jazzy, classic, timeless way.


Following in the footsteps of other great Canadian Folk Artists like Bruce Cockburn, Neil Young, Joni Mitchell, Valdy, Gordon Lightfoot, Stan Rogers and Leonard Cohen, Will has an expansive and eclectic repertoire of his own unique original songs: from whimsical ditties to foot-stomping rockers, heart-breaking ballads and catchy singalongs, exploring Folk, Folk-Rock, Jazz, Cabaret, Blues, Waltzes, Old-Time, Rockabilly, Rock & Roll and other timeless, classic musical styles.


Originally from South Porcupine, northern Ontario, Will is known for his eclectic songwriting, evocative guitar playing and entertaining live show.


Will Gillespie is also the author, composer and director of the award-winning musicals “Swingin’ in St. John’s” and “Diamond in the Rough” 

Will Gillespie has just finished his latest full-length album "MINE! True Stories and Legends of the Porcupine Gold Rush" which he will be releasing live on June 9, 2024 at a Hamilton Arts Week Signature Event Album Release Concert at Fieldcote Memorial Museum and Park in Ancaster, ON.

The album features 12 original Folk songs written in historical styles from Bluegrass to ragtime to Barrelhouse Blues, Music Hall, Waltzes and MORE! telling real-life harrowing tales of adventure and perseverance from a forgotten chapter of Canadian history, taking the listener on a musical journey back in time to a world of prospectors, pioneers, bootlegger-bandits, high-graders, dog-sledders and moonshiners.

2008 - Northern Lights Festival Boreal Meltdown Winner

2008 - Northern Ontario Music Development Program

2020 - Hamilton Arts Awards : Nominee :

Theatre (emerging)

2024, 2023 & 2021 - Community Votes HamiltonPlatinum WinnerBest in Theatre : Chasing Shadows Productions

2024 & 2023 - Hamilton Arts Awards Nominee Short List : Creator Category

2022 - Community Votes HamiltonSilver Winner :

Best in Theatre : Chasing Shadows Productions


Will Gillespie and OWR NLFB 2011 Dancin.jpg

Dancing with the audience at Northern Lights Festival Boreal in Sudbury, Ontario, Canada 

Will Gillespie Six String Nation Guitar.jpg

Playing "Voyageur" the famous six-string nation guitar built out of pieces of Canadian history.

SISJ View Cover.jpg

The original cast of his first musical "Swingin' in St. John's" on the cover of View Magazine.

Getting the crowd moving at the Dakota Tavern in Toronto

At the Westdale Theatre in Hamilton.

MINE Capitol Centre.jpg

At the Capitol Centre in North Bay.

MINE Wink Big Poster.jpg

In front of his "MINE! True Stories and Legends of the Porcupine Gold Rush" play poster at the Westdale Theatre in Hamilton.

TV interview in North Bay

Performing MINE! at the Westdale Theatre

Will and the Statics at River and Sky 20

At River & Sky Camping & Music Festival Beach Stage

Will Gillespie and SALTCOATS at River an

At River Valley Bluegrass Park.

Will Gillespie TH & VS Performance class reunion 2007.jpg

At the William Dawson Auditorium in Timmins.

Will Gillespie and Susan Robinson talking about their cross-Ontario MINE! True Stories and Legends of the Porcupine Gold Rush tour.

Another shot from the Dakota Tavern.

About to play at the Bluebird in Nashville.

Will Gillespie Sound of Music 2021 .jpeg

At the Sound of Music Festival in Burlington.

WG OWR Trio Bandshell Cobourg.jpg

At the Cobourg Waterfront Festival 

Will CHCH Fringe Martians_edited.jpg


Will at NXNE Beaver Guitar Face.jpg

Rockin' out at an official showcase at North By North East at the Supermarket in downtown Toronto. 

Will Gillespie and SALTCOATS NLFB worksh

Will Gillespie (second from right) at a workshop called "On the Sunny Side of the Street" at NLFB with Jackie Washington (left) and Sheesham and Lotus (centre).

BPAC Will Gillespie Jackie Richardson and Mark llama trio Singin

Speaking of Canadian Jazz legends named Jackie that Will had the pleasure and good fortune to sing with...

BPAC Will Gillespie Jackie Richardson and Mark llama Trio Standing O

The Mark Lalama Trio featuring Will Gillespie and Jackie Richardson gratefully receiving a standing ovation at BPAC.

Will Gillespie and OWR at the Local Not one but two accordions II.jpg

Serenading with not one but TWO accordion players.

At the Burlington Performing Arts Centre.

Will Gillespie performing MINE! 

Skinny Will NLFB SALTCOATS.jpg

At Northern Lights Festival Boreal 

In his "Off to the Races" music video Shoot

Crooning and swooning at the Folk Music Ontario conference 

Press Quotes:

"From songwriter to crooner and cabaret man to power pop genius,

Will Gillespie is always evolving his artistry"

- (Paul Loewenberg, Former Artistic Director, Northern Lights Festival Boreal)

"...Will Gillespie has a particular knack for telling imaginative Canadian stories... "  

- (Steel City Girl Reviews)

"If you weren’t watching him live, you’d probably think Gillespie was playing with somebody. He slaps the strings for percussion, plucks out walking baselines, hits some beautiful riffs and arpeggios, and sometimes even manages solos – plus singing or playing harmonica."

- (Beyond James)

"Will Gillespie is a one-of-a-kind,  finger-picking, old-time crooning, genuine songwriter you absolutely MUST see perform" 

- (Matt Thompson)


"the soul of a modern folk jazz troubadour... a true master artist..." 

- (Audio Reckoning)


"His music has the ability to speak deeply to absolutely ANYBODY" 

- (Jeremy Brazeau)

The original Cast of "Swingin' in St. John's" in the Hamilton Spectator

2020 - Gilded Hammer Awards : Nominee :

Groundbreaker Emerging Artist

2024 - Community Votes HamiltonSilver Winner :

Best Entertainer: Will Gillespie

bottom of page