Perhaps it’s the majesty of the hills, the breathtaking views from the top of the Niagara Escarpment or the echoing from the valleys carved out by the glaciers thousands of years ago, that provide the inspiration for the multitude of performers who call the Hills of Headwaters home.
Many would claim the Hills of Headwaters boasts one of the highest concentrations of performers anywhere in this great land. As you travel through the region, you’ll hear the sounds of music, the tapping of toes, the blowing of horns, and the voices of performers bringing life to the written word. The region’s professional stages — heritage opera houses, town halls and churches — provide ideal venues for the multitude of performances that take place year-round.
Listen as well to the sounds coming from community centres, recreational halls, school gymnasiums — just about anywhere that will open their doors to youngsters (of all ages) who are inspired, nurtured and embraced by not only the landscape, but also by the community of passionate performing artists who live and work here.
The flagship professional theatre of the region, Theatre Orangeville, has been entertaining audiences since 1994. Here, in the fully restored, 276-seat heritage Orangeville Town Hall Opera House (where every seat is an orchestra seat), artistic director David Nairn brings some of this country’s finest talents to the region. Nurturing of young talent also sets Theatre Orangeville apart from other theatre companies. Its commitment to youth is apparent in programs like the Theatre Orangeville Youth Singers that provide opportunities for hundreds of youngsters each year to experience the joy of live performing arts.
“These youngsters are our future and our inspiration; it’s our honour and privilege to help them develop their talents and embrace their creativity and it’s our way of giving back to the community that so readily supports everything we do in the theatre,” Nairn says.
In Hillsburgh professional summer theatre can be enjoyed at Century Church Theatre, an intimate venue that provides superior acoustics and is the hub of cultural activity in the community since 1906. Throughout the year, other community performance groups share the space.
Or consider a short drive north to Grace Tipling Hall in Shelburne, standing proudly in the heart of town since 1888. The social centre of the town for decades, with seating for 195 patrons, Grace Tipling Hall offers its stage to performers that include the world-renowned Michael Burgess, and many others eager to share their passion and their talents with audiences from near and far. For generations, amateur community theatre has been thriving in the hills: the award-winning Caledon Town Hall Players have performed in the Old Town Hall in Caledon Village since 1962, and Orangeville Music Theatre has been entertaining audiences since 1979 with full scale productions of Broadway musicals.
When it comes to the sensibilities of rural Canadian life, there may be no Canadian personality better known than Walt Wingfield. A character portrayed by actor Rod Beattie, Wingfield is a former stockbroker who jumped off the corporate ladder to pursue the simpler life of gentleman farming in fictitious Persephone Township. While the character may live in Persephone Township, the inspiration for playwright Dan Needles, the creator of the Wingfield series, was life in the Hills of Headwaters. Needles spent much of his childhood on the family farm near Rosemont, Ont. and began his writing career as editor of the local community newspaper.
In a weekly series of Letters to the Editor, Needles created a column called Letters from Wingfield Farm, and in an address at the University of Waterloo he told an audience that the letters were “his way of compensating for the lack of news in the small town of Shelburne.”
The first stage adaptation of Letters from Wingfield Farm was performed in August of 1984 at the Orange Hall in Rosemont. Now, with six plays in the series, audiences across North America have been introduced to a rural Canadian lifestyle that still exists here in the Hills of Headwaters.
Throughout history, life has been reflected in the music of the day, and if you listen closely you are sure to hear the sound of Celtic music echoing through our hills and valleys. Celtic music — a tribute to the Irish and Scottish who were among the original settlers of our region — is enjoying renewed popularity throughout Canada but the music has long been ringing through the Hills of Headwaters.
The Canadian Open Old Time Fiddle Championship has been attracting thousands of fiddle enthusiasts every year since 1951. Said to be the most important annual event of its kind in Canada, each year thousands of Celtic music devotees travel to Shelburne for five days of family fun. The annual festivities include a Thursday evening concert, fiddle workshops, fiddle jam sessions, qualification events, a fiddle parade, farmer’s market, camping and midway. More than 150 amateur and professional fiddlers from all across Canada compete in eight classes, culminating in the contest finals on Saturday evening where more than $20,000 in prizes are awarded and the Canadian Open Fiddle champion is crowned!
Grassroots passion and community commitment has been the inspiration for the organizers of most of the performance events that take place in the region. For more than 30 years, the Orangeville Concert Association has presented outstanding performing artists to enthusiastic audiences, including acclaimed performances by Moe Koffman, Peter Appleyard, Gene DiNovi, Guido Basso, Carol Welsman and the Elmer Iseler singers.
Since 2003, the Orangeville Blues and Jazz Festival has grown and is now recognized as one of the best of its kind in the country. Each June the festival presents in excesss of 60 acts, 160 performers and brings more than 14,000 blues and jazz enthusiasts to historic downtown Orangeville for this four-day event.
The spectacular landscapes of this region create a perfect stage for artistic pursuits in the Hills of Headwaters. As you escape the city limits, it will be only a matter of time before you start hearing the sounds of music, dance or drama echoing from our historic stages. Come for the day, or spend the night, and experience the intimacy of live performance, as it was meant to be heard, in the Hills of Headwaters.

This article was provided by Michele Harris, executive director of The Hills of Headwaters Tourism Association.