10-Day Festival at an Outdoor Theatre in the Woods (August 7 – 16, 2026). Highlights this Year include Choir! Choir! Choir!, Toronto All-Star Big Band Concert, Gallery in the Woods and Family Day!
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Some Festival Highlights:
- An Evening Aboard the Wenonah II in Support of Muskoka Chautauqua – Enjoy a summer cocktail cruise celebrating arts, culture, and community, supporting Muskoka Chautauqua. Departing from Windermere Wharf.
- Festival Opening & Welcome – August 7th at the outdoor theatre in Windermere. 4pm – 5pm. Free to attend. Enjoy a 10% discount on all food and non-alcoholic beverages from Windermere House Pub during the festival! Show your tickets to the staff for the discount to be applied. Enjoy!.
- Pop-up Book Shop – August 8 – 15, every day 10am-4pm at 2496 Windermere Rd. Come browse and purchase books from the literary guests!
- Choir!Choir!Choir! The Kids Show: Harmonizing the Next Generation. Saturday, August 8th from 3pm – 4pm. Taking place at Windermere United Church. Tickets from $20.
- Choir!Choir!Choir! Presents: An Epic 80’s Sing-Along Saturday, August 8th from 7:30pm to 9pm. Taking place at the Outdoor Theatre under the Stars. Tickets from $70.
- Toronto All Star Big Band – One of the most exciting bands around, the Toronto All-Star Big Band revives the spirit style and sound of the 30’s, 40’s and 50’s. Monday, August 10th 7:30pm to 9:00pm at the Muskoka Chautauqua Theatre in the Woods. Tickets from $40.
- Family Day at Muskoka Chautauqua: Fun for the whole family at the Wharf in Windermere Village! Face painting, arts & crafts, beach games and more! Don’t miss it! 11am to 4pm. Free to attend.
Muskoka Chautauqua Arts & Culture Festival
August 7–16, 2026 | Windermere, Muskoka. Some events are free and some with a charge. All fees support Muskoka Chautauqua, a not-for-profit fostering arts and culture, culminating in a summer festival in the historic village of Windermere.
| Event | Date & Time | Location | Description |
|---|---|---|---|
| An Evening Aboard the Wenonah II | Aug. 6, 5:00 PM | Windermere Wharf | Enjoy an unforgettable evening cruise aboard the Wenonah II in support of Muskoka Chautauqua. |
| Festival Welcome & Opening | Aug. 7, 4:00 PM | Theatre in the Woods | Celebrate the official opening of the 2026 festival with community, culture, and inspiration. |
| Gallery Exhibition Opening: Traditions and Tributaries | Aug. 7, 5:00 PM | Gallery in the Woods | Opening reception for the festival’s featured art exhibition showcasing regional artists. |
| Rising Stars: Singer Songwriters | Aug. 7, 7:30 PM | Theatre in the Woods | Emerging musicians perform original songs in an intimate outdoor concert setting. |
| Pop-Up Bookshop & Exhibition | Aug. 8–15, 10:00 AM Daily | 2496 Windermere Road | Browse books by featured authors and explore literary exhibits throughout the festival. |
| Gallery in the Woods: Traditions and Tributaries | Aug. 8–15, 10:00 AM Daily | Gallery in the Woods | Discover an inspiring collection of artwork celebrating Muskoka’s landscapes and heritage. |
| Windermere History Walking Tour | Aug. 8–15, 12:00 PM Daily | Gallery in the Woods | Guided walking tour exploring the rich history and stories of Windermere Village. |
| The Kids Show: Harmonizing the Next Generation with Choir! Choir! Choir! | Aug. 8, 3:00 PM | Windermere United Church | An interactive musical experience designed to inspire young singers and families. |
| Author Insights: A Chat with Patrick Boyer | Aug. 8, 4:00 PM | Theatre in the Woods | Join author Patrick Boyer for an engaging discussion about his work and writing journey. |
| Choir! Choir! Choir! Presents: An EPIC 80’s Sing-Along | Aug. 8, 7:30 PM | Theatre in the Woods | Sing your heart out to iconic 1980s hits in this high-energy audience participation event. |
| Clay Whistle & Clay Rattle Workshop with Audrey Mah | Aug. 9, 10:00 AM | Gallery in the Woods | Learn traditional clay-making techniques while creating your own functional art pieces. |
| Jennifer Tung & Friends | Aug. 9, 2:30 PM | Christ Church | Acclaimed pianist Jennifer Tung and guests perform a beautiful afternoon of classical music. |
| Love Notes From Your Soul: Connecting With Your Inner Wisdom | Aug. 9, 4:00 PM | Windermere Community Centre | A reflective workshop designed to help participants reconnect with creativity and intuition. |
| Caroline Marie Brooks | Aug. 9, 7:30 PM | Theatre in the Woods | Juno Award-winning singer-songwriter Caroline Marie Brooks performs an evening of folk-inspired music. From The Good Lovelies |
| Science, Crafts & Curiosity with Friends of the Muskoka Watershed | Aug. 10, 10:00 AM | Gallery in the Woods | Family-friendly activities exploring nature, science, and environmental stewardship. |
| Community Song Circle with Caroline Marie Brooks | Aug. 10, 4:00 PM | Theatre in the Woods | Gather in song and community through a participatory musical experience. |
| Toronto All-Star Big Band Concert | Aug. 10, 7:30 PM | Theatre in the Woods | Experience the sounds of the swing era with one of Canada’s premier big bands. |
| Graffiti Embroidery with Barbara Klunder | Aug. 11, 10:00 AM | Gallery in the Woods | A creative workshop blending embroidery, storytelling, and artistic expression. |
| Author Insights: A Chat with Janet Stahle | Aug. 11, 4:00 PM | Theatre in the Woods | Hear from author Janet Stahle as she discusses her latest work and creative process. |
| Maggie’s Wake | Aug. 11, 7:30 PM | Theatre in the Woods | Enjoy an evening of Celtic-inspired music filled with energy, storytelling, and tradition. |
| Painting Along with the Bala Plein Air Group | Aug. 12, 9:00 AM | Windermere House | Create alongside local artists while capturing the beauty of Muskoka’s landscapes. |
| Visual Notetaking with Pam Hubbard | Aug. 12, 10:00 AM | Windermere Community Centre | Learn techniques for transforming ideas into engaging visual notes and sketches. |
| Windermere Community Conversation | Aug. 12, 4:00 PM | Windermere House | Join community members in a thoughtful discussion about the future of Windermere. |
| A Night of Taizé | Aug. 12, 7:30 PM | Windermere United Church | An evening of music, reflection, and contemplation in a peaceful candlelit setting. |
| En Plein-Air Painting Workshop with Greg & Sue Hindle | Aug. 13, 10:00 AM | Gallery in the Woods | Develop your outdoor painting skills while drawing inspiration from Muskoka’s scenery. |
| Author Insights: Listening to Your Light | Aug. 13, 1:00 PM | 2496 Windermere Road | An inspiring author presentation exploring personal growth and self-discovery. |
| Muskoka Philharmonic Orchestra | Aug. 13, 7:30 PM | Theatre in the Woods | Enjoy an evening of orchestral music performed by talented local musicians. |
| Botanical Relief Casting with Sharon Wagner-Chazalon | Aug. 14, 10:00 AM | Gallery in the Woods | Create detailed botanical casts inspired by the natural beauty of Muskoka. |
| Author Insights: A Chat with Fay Martin | Aug. 14, 4:00 PM | Theatre in the Woods | Meet author Fay Martin and learn about her writing and creative inspirations. |
| Folk Night with Beverlie & Friends | Aug. 14, 7:30 PM | Theatre in the Woods | A lively evening of folk music featuring Beverlie Robertson and special guests. |
| Sketching & Watercolour in Nature with Natalia Laluq | Aug. 15, 10:00 AM | Gallery in the Woods | Explore nature journaling and watercolour techniques in a hands-on workshop. |
| Author Insights: A Chat with Tim Falconer | Aug. 15, 4:00 PM | Theatre in the Woods | Join award-winning author Tim Falconer for an engaging literary conversation. |
| Northern Lights Steel Orchestra Waterfront Concert | Aug. 15, 7:30 PM | Windermere Wharf | Enjoy an energetic waterfront concert featuring Caribbean-inspired steel pan music. |
| Windermere Family Fun Day | Aug. 16, 10:00 AM | Windermere Wharf | Festival finale featuring family activities, entertainment, games, crafts, and community fun. |
