Events in Downtown Oakville

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May 2016

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25

Date Night Special at Paradiso

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27

Wine Not Wednesday’s at Paradiso

28

Martini Night at J Bistro

Live Music at O’Finns Irish Temper

29

Jazz Night at Paradiso every Friday!

Live Music at O’Finns Irish Temper

30

Black Forest & Team Newton Spinning day

Live Music at O’Finns Irish Temper

1

Free Classes @ Titika Active Couture

2

Date Night Special at Paradiso

3
4

Wine Not Wednesday’s at Paradiso

5

Martini Night at J Bistro

Live Music at O’Finns Irish Temper

6

Jazz Night at Paradiso every Friday!

Live Music at O’Finns Irish Temper

7

Live Music at O’Finns Irish Temper

8

Free Classes @ Titika Active Couture

9

Date Night Special at Paradiso

10
11

Wine Not Wednesday’s at Paradiso

12

Martini Night at J Bistro

Live Music at O’Finns Irish Temper

13

Jazz Night at Paradiso every Friday!

Live Music at O’Finns Irish Temper

14

Ten Thousand Villages – World Fair Trade Day

Live Music at O’Finns Irish Temper

15

Free Classes @ Titika Active Couture

16

Date Night Special at Paradiso

17
18

Oakville Historical Society Speaker’s Night

Wine Not Wednesday’s at Paradiso

19

Martini Night at J Bistro

Sun Life Financial Career Information Seminar

Live Music at O’Finns Irish Temper

20

Jazz Night at Paradiso every Friday!

Live Music at O’Finns Irish Temper

21

Oakville Horticultural Society Plant Sale

Live Music at O’Finns Irish Temper

22

Free Classes @ Titika Active Couture

23

Date Night Special at Paradiso

24
25

Wine Not Wednesday’s at Paradiso

26

Martini Night at J Bistro

Good For Me Naturally – Onsite Seminar

Live Music at O’Finns Irish Temper

27

Jazz Night at Paradiso every Friday!

Live Music at O’Finns Irish Temper

28

Live Music at O’Finns Irish Temper

29

Free Classes @ Titika Active Couture

Oakville Purina Walk For Dog Guides

30

Date Night Special at Paradiso

31
1

Wine Not Wednesday’s at Paradiso

2

Martini Night at J Bistro

Good For Me Naturally – Onsite Seminar

Live Music at O’Finns Irish Temper

3

Jazz Night at Paradiso every Friday!

Live Music at O’Finns Irish Temper

4

Oakville Farmer’s Market & Cultural Activities

An Evening with Charter Ability

Live Music at O’Finns Irish Temper

5

Free Classes @ Titika Active Couture

Plein Air Painting in Downtown Oakville

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Featured Events


  • Plein Air Painting in Downtown Oakville

    Paint the Town Extraordinaire: Plein Air Painting in Downtown Oakville is in its second year. Artis...

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  • Sidewalk Sale

    Downtown Oakville will be hosting the 43rd annual Sidewalk Sale from Thursday, June 9 to Sunday, ...

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  • Midnight Madness

    6pm-Midnight: Enjoy Oakville’s largest retail event of the year, featuring incredible sales, ...

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  • TD Downtown Oakville Jazz Festival

    Celebrating its 24th year, the TD Downtown Oakville Jazz Festival provides an amazing weekend f...

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  • Tiny Tots on Parade

    Calling all Trick-or-Treaters!  Come on down to Downtown Oakville’s Towne Square and show us...

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  • Tree Lighting Ceremony

    The Downtown Oakville Tree Lighting Ceremony will begin at 6 p.m. located in the Town Square to kic...

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  • Santa in the Square

      Share your Christmas wishlist and get your photo taken with Santa in the magical setting of Tow...

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  • Wagon Rides with Santa & Carolers

    Saturdays & Sundays November 26– December 24, 2016 11:00am-4:00 pm Whether you’re finis...

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Past Events


  • A Taste of Oakville


    A Taste of Oakville January 26- February 12, 2015 visit atasteofoakville.com for participating restaurants and menu's For the first time this year restaurants from across Oakville have combined for A Taste of Oakville.and promises to be a culinary treat. Discover the fabulous restaurants that O...

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  • "Sale" Into Summer Makeover Contest


    Morning Live and the Downtown Oakville BIA want you to “Sale Into Summer” with a Summer makeover! To enter, email us at makeover@chch.com and tell us why you or someone special in your life deserves a summer makeover! Please include your contact information along with a photo. One female and on...

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  • Midnight Madness presented by Scotiabank


    6pm-Midnight: Enjoy Oakville’s largest retail event of the year, featuring incredible sales, food, live music, entertainment and lots of community spirit! With over 6 blocks of brag-worthy deals and free family-friendly entertainment available right through to midnight, this is an evening of excit...

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  • TD Downtown Oakville Jazz Festival Kick Off Concert


    Emily Claire-Barlow Performs at the Kick Off Concert to TD Downtown Oakville Jazz Festival! August 6, 2015 at 8:00pm at the Oakville Centre for Performing Arts Having just returned from Holland, where she recorded with world renowned jazz orchestra the Metropole Orkest, Emilie-Claire is poised...

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  • TD Downtown Oakville Jazz Festival


    Celebrating its 23rd year, the Downtown Oakville Jazz Festival provides an amazing weekend for the entire family. Enjoy outdoor patios, great shopping, fantastic dining and excellent entertainment! This FREE event showcases over a dozen bands on several stages throughout the downtown, includi...

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  • Late Night Thursdays in Downtown Oakville


    Thursdays are the new Fridays in Downtown Oakville!  With buskers & giant games from 6pm - 9pm, shopping, dining specials and of course, FREE parking after 6pm, Oakville comes alive every Thursday night, on now through to September 24. Before you hit the cottage or get caught up in weekend hu...

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  • Late Night Thursdays in Downtown Oakville


    Thursdays are the new Fridays in Downtown Oakville!  With buskers & giant games from 6pm - 9pm, shopping, dining specials and of course, FREE parking after 6pm, Oakville comes alive every Thursday night, on now through to September 24. Before you hit the cottage or get caught up in weekend hu...

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  • Late Night Thursdays in Downtown Oakville


    Thursdays are the new Fridays in Downtown Oakville!  With buskers & giant games from 6pm - 9pm, shopping, dining specials and of course, FREE parking after 6pm, Oakville comes alive every Thursday night, on now through to September 24. Before you hit the cottage or get caught up in weekend hu...

    VIEW MORE
  • Late Night Thursdays in Downtown Oakville


    Thursdays are the new Fridays in Downtown Oakville!  With buskers & giant games from 6pm - 9pm, shopping, dining specials and of course, FREE parking after 6pm, Oakville comes alive every Thursday night, on now through to September 24. Before you hit the cottage or get caught up in weekend hu...

    VIEW MORE
  • Late Night Thursdays in Downtown Oakville


    Thursdays are the new Fridays in Downtown Oakville!  With buskers & giant games from 6pm - 9pm, shopping, dining specials and of course, FREE parking after 6pm, Oakville comes alive every Thursday night, on now through to September 24. Before you hit the cottage or get caught up in weekend hu...

    VIEW MORE
  • Late Night Thursdays in Downtown Oakville


    Thursdays are the new Fridays in Downtown Oakville!  With buskers & giant games from 6pm - 9pm, shopping, dining specials and of course, FREE parking after 6pm, Oakville comes alive every Thursday night, on now through to September 24. Before you hit the cottage or get caught up in weekend hu...

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  • British Invasion Day


    Join us on Saturday September 19th for British-themed dancing in Bronte Village (Bronte Mall outside of British Eats and Treats and Centriller Square outside of Denninger’s), Downtown (Towne Square) and Kerr Village (Heritage Park Square) throughout the afternoon. Enjoy live music act, Strange...

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  • Late Night Thursdays in Downtown Oakville


    Thursdays are the new Fridays in Downtown Oakville!  With buskers & giant games from 6pm - 9pm, shopping, dining specials and of course, FREE parking after 6pm, Oakville comes alive every Thursday night, on now through to September 24. Before you hit the cottage or get caught up in weekend hu...

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  • Autumn Harvest Event


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  • Santa in the Square


    Saturday, November 28, 2015 11:00am-1:00pm Share your Christmas wishlist and get your photo taken with Santa in the magical setting of Towne Square, with it's beautiful Christmas tree, music, holiday treats and more for all ages to enjoy! Photos with Santa is available and FREE to all!  &nb...

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  • Wagon Rides with Santa & Carolers in Downtown Oakville


    Saturdays & Sundays November 28 - December 20, 2015 11:00am-4:00 pm Whether you're finishing your Christmas shopping, preparing your home and self for the holidays, picking up a treat for a host, or out dining and celebrating the season, you can enjoy crossing off your holiday 'to-do list' i...

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  • Shop the Neighbourhood


    Experience Downtown Oakville's Shop the Neighbourhood Event! Join us for this ONE DAY promotional event to celebrate everything local showcasing all the fantastic shopping, dining, and professional services that there is available in Downtown Oakville! Look for the Shop the Neighbourhood windo...

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  • Wagon Rides with Santa & Carolers in Downtown Oakville


    Saturdays & Sundays November 28 - December 20, 2015 11:00am-4:00 pm Whether you're finishing your Christmas shopping, preparing your home and self for the holidays, picking up a treat for a host, or out dining and celebrating the season, you can enjoy crossing off your holiday 'to-do list' i...

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  • Wagon Rides with Santa & Carolers in Downtown Oakville


    Saturdays & Sundays November 28 - December 20, 2015 11:00am-4:00 pm Whether you're finishing your Christmas shopping, preparing your home and self for the holidays, picking up a treat for a host, or out dining and celebrating the season, you can enjoy crossing off your holiday 'to-do list' i...

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  • Wagon Rides with Santa & Carolers in Downtown Oakville


    Saturdays & Sundays November 28 - December 20, 2015 11:00am-4:00 pm Whether you're finishing your Christmas shopping, preparing your home and self for the holidays, picking up a treat for a host, or out dining and celebrating the season, you can enjoy crossing off your holiday 'to-do list' i...

    VIEW MORE
  • Wagon Rides with Santa & Carolers in Downtown Oakville


    Saturdays & Sundays November 28 - December 20, 2015 11:00am-4:00 pm Whether you're finishing your Christmas shopping, preparing your home and self for the holidays, picking up a treat for a host, or out dining and celebrating the season, you can enjoy crossing off your holiday 'to-do list' i...

    VIEW MORE
  • Wagon Rides with Santa & Carolers in Downtown Oakville


    Saturdays & Sundays November 28 - December 20, 2015 11:00am-4:00 pm Whether you're finishing your Christmas shopping, preparing your home and self for the holidays, picking up a treat for a host, or out dining and celebrating the season, you can enjoy crossing off your holiday 'to-do list' i...

    VIEW MORE
  • Wagon Rides with Santa & Carolers in Downtown Oakville


    Saturdays & Sundays November 28 - December 20, 2015 11:00am-4:00 pm Whether you're finishing your Christmas shopping, preparing your home and self for the holidays, picking up a treat for a host, or out dining and celebrating the season, you can enjoy crossing off your holiday 'to-do list' i...

    VIEW MORE
  • Wagon Rides with Santa & Carolers in Downtown Oakville


    Saturdays & Sundays November 28 - December 20, 2015 11:00am-4:00 pm Whether you're finishing your Christmas shopping, preparing your home and self for the holidays, picking up a treat for a host, or out dining and celebrating the season, you can enjoy crossing off your holiday 'to-do list' i...

    VIEW MORE
  • A Taste of Oakville


    A Taste of Oakville features 25 of Oakville’s best restaurants offering signature prix-fixe lunch and/or dinner menus. With prix-fixe menus that offer amazing value and vast culinary selection, your taste-buds can travel the world without leaving Oakville! View participating restaurants and men...

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  • Sledge in the Square


    Join us for an afternoon of fun at ‘Sledge in the Square’ on February 6, 2016 from 1pm – 3pm, in the Towne Square.  Meet RBC Olympian Tyler McGregor, Canadian Sledge Hockey bronze medalist, and learn more about what sledge hockey is all about.  Enjoy live music by the Oakville School of ...

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  • Egg-sperience Downtown Oakville: Not your typical Easter egg hunt!


      This year Downtown Oakville is pleased to present a brand new event – Egg-sperience Downtown Oakville: Not your typical Easter egg hunt! This hunt will include great prizes for everyone to enjoy; grown-ups and kids alike!  With prizes such as a luxury car for the weekend, gift certi...

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