10-Day Festival at an Outdoor Theatre in the Woods (Save the Date – August 6 – 15, 2027).
Highlights this Year include Choir! Choir! Choir!, Toronto All-Star Big Band Concert, Gallery in the Woods and Family Day!
Muskoka Chautauqua’s Summer Festival is taking place from August 6th to 15th, 2027 in Village of Windermere. This year’s festival will take place in intimate venues throughout this walkable village, with most events hosted in an open-air theatre in the woods overlooking Lake Rosseau, just as they were 100 years ago. Visitors will have the opportunity to connect and share art, culture, and literature. Visitors can draw inspiration from the picturesque scenery around them, from the bright stars at night to the lush forest by day. These views will also be the backdrop to many activities during the festival including lectures, live music, art workshops and engaging sessions. Overlooking Lake Rosseau and situated in the woods, this is the perfect setting to connect with art, culture, and oneself. Many tickets are free or low entrance fee.
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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. |
