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Discover Downtown Oakville's outdoor shopping experience, your festive destination where history and modern charm collide. Explore historical buildings and trendy boutique shops while enjoying international cuisine. Take in the charming store displays and the spectacular Winter Wonderland of Lights. And don't miss these hometown holiday events for a guaranteed festive season!

Holiday Happenings 

  • Mi Casa Your Casa 2.0
    Mi Casa Your Casa 2.0
    Tue, Aug 27
    Towne Square
    Aug 27, 2024, 10:00 a.m. – Sep 19, 2024, 11:00 p.m.
    Towne Square, Oakville, ON L6J 1H8, Canada
    Experience the lively spirit of Latin American mercados at "Mi Casa, Your Casa 2.0," where red frames shaped like tiny houses offer a welcoming glow and swings to connect and relax in a playful, communal setting.
  • Stroller Socials
    Stroller Socials
    Multiple Dates
    Wed, Sep 18
    Towne Square
    Sep 18, 2024, 11:00 a.m. – 12:00 p.m.
    Towne Square , Oakville, ON L6J 1H8, Canada
    Join our weekly Stroller Socials for a leisurely walk through the historic streets of Downtown Oakville, followed by coffee and conversation with fellow moms.
  • Fall Connections: Member Networking Social
    Fall Connections: Member Networking Social
    Wed, Sep 18
    Towne Square Gallery
    Sep 18, 2024, 6:00 p.m. – 8:00 p.m.
    Towne Square Gallery, 94 George St Unit 4, Oakville, ON L6J 3B7, Canada
    Mark your calendars for our Fall Member Networking & Social event. Join us for an evening of connection and collaboration with fellow Downtown Oakville members.
  • Fun Run
    Fun Run
    Multiple Dates
    Wed, Sep 18
    Running Room
    Sep 18, 2024, 6:00 p.m. – 7:00 p.m.
    Running Room, 156 Lakeshore Rd E, Oakville, ON L6J 1H4, Canada
    Join the Running room every Wednesday at 6PM for a fun free social group run!
  • Sound Ceremony Meditation
    Sound Ceremony Meditation
    Multiple Dates
    Thu, Sep 19
    Zazen Meditation & Self-care Studio
    Sep 19, 2024, 7:00 p.m. – 8:30 p.m.
    Zazen Meditation & Self-care Studio, 251 Lakeshore Rd E, Oakville, ON L6J 1H9, Canada
    Enjoy a Sound Ceremony Meditation with Zazen Meditation & Self-care Studio.
  • Single in the City Dating inc.
    Single in the City Dating inc.
    Fri, Sep 20
    Figaro Coffee House
    Sep 20, 2024, 7:30 p.m. – 9:30 p.m.
    Figaro Coffee House, 350 Lakeshore Rd E, Oakville, ON L6J 1J6, Canada
    Get ready for a fun and flirty Trivia Night where mingling is the name of the game! Show off your smarts, compete for prizes, and connect with other singles.
  • Synchronized - Elle Belz Art Exhibition
    Synchronized - Elle Belz Art Exhibition
    Sat, Sep 21
    Towne Square Gallery
    Sep 21, 2024, 12:00 p.m. – Oct 19, 2024, 4:00 p.m.
    Towne Square Gallery , 94 George St, Oakville, ON L6J 1H6, Canada
    Enjoy the beautiful works of Synchronized - a solo exhibition of Elle Belz mixed media paintings.
  • Sacred Breathwork Movement
    Sacred Breathwork Movement
    Multiple Dates
    Sat, Sep 21
    Zazen Meditation & Self-care Studio
    Sep 21, 2024, 1:30 p.m. – 3:30 p.m.
    Zazen Meditation & Self-care Studio, 251 Lakeshore Rd E, Oakville, ON L6J 1H9, Canada
    Experience a journey inwards re-balancing your nervous system reconnecting you to your intuition utilizing Sound, Breath and Movement with Zazen Meditation & Self-care Studio.
  • Silent Disco - Taylor Swift - The Eras Tour
    Silent Disco - Taylor Swift - The Eras Tour
    Sat, Sep 21
    Towne Square
    Sep 21, 2024, 5:00 p.m. – 9:00 p.m.
    Towne Square, Oakville, ON L6J, Canada
    Calling all Swifties! Get ready to dance the night away at our Taylor Swift Themed Silent Disco: Eras Tour Edition. Join us for an unforgettable evening featuring a full Eras Tour playlist that spans Taylor’s iconic career, from her early hits to her Torturered Poets chart toppers.
  • Silent Yoga
    Silent Yoga
    Sun, Sep 22
    Towne Square
    Sep 22, 2024, 10:00 a.m. – 11:00 a.m.
    Towne Square, Oakville, ON L6J 1H8, Canada
    Join us for an unforgettable Silent Yoga experience in Towne Square on September 22 at 10 AM!
  • Reiki Healing Workshop
    Reiki Healing Workshop
    Multiple Dates
    Sun, Sep 22
    Zazen Meditation & Self-care Studio
    Sep 22, 2024, 10:30 a.m. – 5:30 p.m.
    Zazen Meditation & Self-care Studio, 251 Lakeshore Rd E, Oakville, ON L6J 1H9, Canada
    Discover the transformative power of Reiki with Zazen Meditation & Self-care Studio!
  • Tuscany Cooking Class
    Tuscany Cooking Class
    Sun, Sep 22
    Paradiso Restaurant
    Sep 22, 2024, 6:30 p.m. – 9:30 p.m.
    Paradiso Restaurant , 125 Lakeshore Rd E, Oakville, ON L6J 1H4, Canada
    Experience a hands-on cooking experience guided by a talented chef at Paradiso!
  • Paradiso Classics Cooking School
    Paradiso Classics Cooking School
    Mon, Sep 23
    Paradiso Restaurant
    Sep 23, 2024, 6:30 p.m. – 9:30 p.m.
    Paradiso Restaurant, 125 Lakeshore Rd E, Oakville, ON L6J 1H4, Canada
    Experience a hands-on cooking experience guided by a talented chef at Paradiso Restaurant.
  • Pizza Making Workshop
    Pizza Making Workshop
    Mon, Sep 23
    Mercato Sociale
    Sep 23, 2024, 6:30 p.m. – 9:00 p.m.
    Mercato Sociale, 257 Lakeshore Rd E, Oakville, ON L6J 1H9, Canada
    Enjoy a pizza making workshop with Chef Enzo Campisi at Mercato Sociale!
  • Pups & Pints
    Pups & Pints
    Multiple Dates
    Tue, Sep 24
    Paradiso Downtown Oakville
    Sep 24, 2024, 7:00 p.m. – 11:00 p.m.
    Paradiso Downtown Oakville, 125 Lakeshore Rd E, Oakville, ON L6J 1H3, Canada
    Join us for a tail-wagging good time at Pups & Pints Tuesdays on Paradiso's Pup-Up Patio!
  • Oakville Speed Dating Ages 35-48)
    Oakville Speed Dating Ages 35-48)
    Tue, Sep 24
    Paradiso
    Sep 24, 2024, 7:30 p.m. – 9:30 p.m.
    Paradiso, 125 Lakeshore Rd E, Oakville, ON L6J 1H4, Canada
    Go on fun, fast dates and meet up to 15 new people in one fun night with Single in the City and Paradiso!
  • The Pack: Downtown Oakville's Dog Walking Club
    The Pack: Downtown Oakville's Dog Walking Club
    Multiple Dates
    Wed, Sep 25
    Towne Square
    Sep 25, 2024, 6:00 p.m. – 8:00 p.m.
    Towne Square, Oakville, ON L6J 1H8, Canada
    Join The Pack, Downtown Oakville's Dog Walking Club. Enjoy a monthly group walk and socializing session with your furry friends! After a stroll, relax and enjoy pints with the pups on a participating patio. Treats included. Registration Required. In Partnership with Whittall-Chuang Real Estate
  • Mastery Balance & Self-trust Collective Coaching
    Mastery Balance & Self-trust Collective Coaching
    Fri, Sep 27
    Zazen Meditation & Self-care Studio
    Sep 27, 2024, 11:00 a.m. – 12:15 p.m.
    Zazen Meditation & Self-care Studio, 251 Lakeshore Rd E, Oakville, ON L6J 1H9, Canada
    Join this supportive group coaching experience designed for women to take control of their time while honouring the commitments they make to themselves with Zazen Meditation & Self-care Studio.
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