Oakville’s cultural scene is a captivating blend of historical charm and contemporary vibrancy. Its rich heritage is highlighted through charming historic sites and a dynamic arts scene, while local events and festivals create a warm, intimate atmosphere. Explore with us and experience how heritage and modern artistry blend seamlessly.
1:00 p.m. – 4:00 p.m.
Erchless Estate
8 Navy Street
Erchless Estate, Oakville’s own Downton Abbey, invites guests to step into a world where history and elegance intertwine. Once the residence of the Chisholm family for six generations, the estate offers a rare glimpse into the stories that shaped the town and the diverse communities that continue to enrich its legacy. This season, its halls are graced with an exquisite exhibition of 1920s and 1930s gowns and accessories from the Oakville Museum’s collection—garments of flowing silhouettes, delicate beadwork, and timeless glamour that reflect both artistry and a transformative era.
10:00 a.m. – 5:00 p.m.
Oakville Galleries: Gairloch Gardens
1306 Lakeshore Road East
This immersive exhibition introduces a striking new body of sculptural work that intimately engages with the gallery’s architecture and natural surroundings. Drawing inspiration from Juhani Pallasmaa’s metaphor on sensory architecture, Santana explores the emotional resonance of touch—where a door handle, like a handshake, becomes a subtle communicator of intention and design. With minimalist finesse and poetic restraint, her mesh and glass works investigate authorship, gender, and corporeal memory, crafting a space where art, body, and environment quietly intertwine.
10:00 a.m. – 5:00 p.m.
Oakville Galleries: Centennial Square
120 Navy Street
Oakville Galleries presents a captivating large-scale installation by Hugo Canoilas. This immersive, floor-based painting envelops the gallery, guiding visitors across a richly textured visual field inspired by deep-sea life. Originally created for an operatic setting in Austria, the piece has been reimagined for Oakville—its form evolving to echo and challenge the unique contours of the space. Through luminous ROV-inspired lighting and evocative imagery of octopus skin, shells, and siphonophores, the installation explores symbiosis, transformation, and the quiet power of nature made monumental through art.
7:15 p.m.
Oakville Museum
8 Navy Street
Oakville’s storied past takes a haunting turn in this immersive evening experience curated by the Oakville Historical Society. The evening unfolds with a candlelit tour through the historic streets of Downtown Oakville, guided by spectral figures drawn from the town’s past—perhaps a former mayor, a merchant, or the wife of a 19th-century doctor. Along the route, chilling tales and eerie encounters unfold against the backdrop of the Erchless Estate. The evening concludes at a charming downtown pub, where guests can share ghost stories over a specialty cocktail—a refined blend of folklore, history, and atmospheric intrigue.
6:30 p.m. & 8:00 p.m.
Oakville Historical Society
110 King Street
This spirited seasonal experience from the Oakville Historical Society invites families to celebrate Halloween with a touch of history and a dash of the supernatural. Guests are guided through the storied streets of Old Oakville by ghostly figures from the 1800s—each sharing tales that illuminate the town’s rich past. Thoughtfully designed to be both educational and family-friendly, the walks blend local lore with light-hearted charm. After the tour, guests are welcomed to enjoy light refreshments and conversation, creating a warm, community-driven conclusion to an evening of historic enchantment and gentle Halloween intrigue.
10:30 a.m.
Oakville Trafalgar Community Center to George's Square
325 Reynolds Street to 179 Trafalgar Road
Pause, reflect, and honour the brave men and women who have served and continue to serve Canada in times of war, conflict, and peace. The town’s annual Remembrance Day Parade will begin at the Oakville Trafalgar Community Centre on Reynolds Street and proceed to George’s Square, where a commemorative ceremony will follow. Residents are encouraged to wear the symbolic poppy, observe two minutes of silence at 11 a.m., or share messages of gratitude using #OakvilleRemembers—a poignant tribute to courage, sacrifice, and enduring national pride.
5:00 p.m. – 9:00 p.m.
Towne Square
210 Lakeshore Road East
Downtown Oakville comes alive with the warmth and wonder of the season during its Hometown Holiday Celebrations. The streets shimmer with festive charm as the annual tree lighting illuminates the heart of town, setting the stage for a truly magical experience. Throughout the season, every Saturday, families are invited to revel in timeless traditions—from enchanting Candy Cane Carollers and elegant horse-drawn carriage rides to heartwarming photos with Santa and indulgent cups of hot cocoa. It’s a captivating celebration where Oakville’s signature sophistication meets the joy of the holidays.
6:30 p.m.
Knox Presbyterian Church
89 Dunn Street
Candlelight Concerts bring a touch of magic to Oakville with a beautifully immersive musical experience like no other. Set in the elegant Knox Presbyterian Church and illuminated by the soft flicker of candlelight, this special evening features the iconic music of Queen vs. ABBA, reimagined by the talented Listeso String Quartet. From “Dancing Queen” to “Bohemian Rhapsody”, guests will be swept away by a stunning blend of sound and atmosphere. This 60-minute concert offers a unique and memorable night out—elevated, intimate, and full of feeling. It’s a chance to experience your favourite songs in a truly unforgettable setting.
8:45 p.m. & 6:30 p.m., Respectively
Knox Presbyterian Church
89 Dunn Street
Candlelight Concerts bring a touch of magic to Oakville with a beautifully immersive musical experience like no other. Set in the elegant Knox Presbyterian Church and illuminated by the soft flicker of candlelight, this special evening features the iconic music of Vivaldi's Four Seasons & more, by the talented Listeso String Quartet. From “La primavera” to “L'inverno”, guests will be swept away by a stunning blend of sound and atmosphere. This 60-minute concert offers a unique and memorable night out—elevated, intimate, and full of feeling. It’s a chance to experience your favourite songs in a truly unforgettable setting.
9:00 a.m
Downtown Oakville
210 Lakeshore Road East
The Oakville Santa Claus Parade returns with its signature charm and timeless spirit, delighting the community with this year’s enchanting theme “Snow Much Fun!” A celebration of winter’s pure joy, it captures the magic of skating, sledding, and all the snowy adventures that make the season sparkle. For over seven decades, the parade has united Oakville’s residents, young and young at heart, in a shared moment of wonder. What began in 1948 as a downtown initiative has evolved into a cherished tradition—one that continues to embody the heart of Oakville’s holiday season.
1:30 p.m.
Oakville Museum
8 Navy Street
Step into the timeless elegance of Erchless Estate, where the spirit of the season is brought to life in magnificent detail. Each room is adorned with festive décor, evoking the warmth and charm of Christmases past. Explore cherished traditions, admire a curated display of classic toys, and create your own festive craft as a keepsake of the experience. Blending heritage and holiday enchantment, this beautifully preserved estate offers a refined glimpse into the artistry and celebration of Oakville’s storied past—a true seasonal delight.
3:00 p.m. – 5:00 p.m.
Towne Square
94 George Street
Experience the magic of the season with The Candy Cane Carollers, Toronto’s premier holiday entertainers. Their enchanting performances will fill your heart with festive cheer and create unforgettable memories.
2:00 p.m. - 6:00 p.m.
Towne Square - Pick up at Robinson Street
325 Reynolds Street
Enjoy a ten minute Horse and Carriage ride through the historic Downtown Oakville neighbourhood and take in the beautiful sites along the way! Purchase a ticket and help support United Way.
5:00 p.m. - 6:00 p.m.
Towne Square
94 George Street
Chartwell Church invites the Oakville community to “Carols in the Square” on Christmas Eve from 5:00 to 6:00 pm. Join us for carol singing, hot chocolate, and cookies. There is an opportunity bring a non-perishable food item to support Kerr Street Mission’s foodbank. All are welcome!
10:00 a.m. - 5:00 p.m.
Bronte Creek Provincial Park
1219 Burloak Drive
Relax with your family and step back in time to 1899 to see how an early settler family celebrated Christmas. You will learn about why and how some of the traditions started and continue to this day. Enjoy house tours, crafts, music, story time, and refreshments. Plan to spend about 2 hours enjoying all the activities.
Queen Elizabeth Park Community & Cultural Centre
2302 Bridge Road
Artwork will be displayed in the corridors of QEPCCC, with the theme 'Timeless', inviting a wide range of creative interpretations. The pieces will capture the past, present, and future, allowing your imagination to soar!
Participating Restaurants - List Coming Soon!
The Taste of Oakville is an exquisite culinary celebration. This premier event showcases a selection of Oakville's finest restaurants, spanning Downtown, Bronte, Kerr Village, and beyond, offering indulgent prix-fixe lunch and dinner menus, some restaurants are also featuring live music!
We invite you to explore and fall in love with Oakville, just as we have—your next chapter awaits.
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