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Fun Events In And Around Oakville September 23-25th 2022

“I come alive in the fall time.” — The Weeknd 

The Weekend and The Weeknd are both upon us. If you can, head over to Rogers Centre to see The Weeknd’s ‘After Hours Til Dawn’ stadium show tonight.  Sweater weather and fall have also officially arrived. It’s uncanny how the temperature dropped yesterday for the first day of fall.  For those of us who live for summer, summertime sadness is about to set in. 

There’s lots of Fall Festivals happening this weekend! Don’t miss out! See my list of fun events below. 

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Friday September 23rd

The Weeknd @ Rogers Centre
Hello Toronto! The Weeknd is home with his ‘After Hours Til Dawn Tour’ –  29 song set list
6:30 p.m. 
1 Blue Jays Way, Toronto , ON

Outdoor Indigenous Movie Night @ Oakville Museum
Watch Indigenous films on the grounds of the Oakville Museum. The night, will feature the films Honour to Senator Murray Sinclair and Hi-Ho Mistahey! 
6:00 p.m.
8 Navy St., Oakville, ON

Milton Fall Fair @ Milton Fairgrounds
The 167th Milton Fall Fair returns Friday September 23 to Sunday September 25, 2022!
3 p.m.
136 Robert Street Milton, ON

 Hops and Harvest Festival @ Area 8 Halton Conservation (Kelso Quarry)
Hops & Harvest is an autumn festival that features local food, beverage, and artisan vendors while celebrating the great outdoors. Inspired by the changing colours of the escarpment, the patchwork of farm fields and the abundance of fresh farmers’ market produce
2 p.m. – 9 p.m.
5347 Steeles Ave W
Milton, ON

Saturday September 24th

Oakville’s Civitan Farmer’s Market @ Dorval Crossing East
Shop fresh and local every Saturday! Support our Farmers who work long and hard to feed us.
8 a.m. to 2 p.m
200 North Service Rd, West Oakville, ON

Trunk Sale @
An event in the parking lot at featuring an assortment of treasures to be found while supporting Ukraine Relief.
8 a.m. – 12 p.m.
171 Speers Rd., Oakville, ON

Hamilton Comic Con @ Canadian Warplane Heritage Museum
Hamilton Comic Con is Hamilton’s premier pop culture event. Over 100,000 square feet of vendors, artists, celebrities, autographs, photo ops, attractions, Q&As and panels, cosplay contest and so much more!
10:00 a.m. – 4 p.m.
9280 Airport Road Hamilton, ON 

Nish Dish Pop-Up @ Crawford Lake
Enjoy the beauty of the forest, rare meromictic lake, and reconstructed longhouse village, followed up with a delicious Indigenous meal. From bison sausage to wild rice to strawberry juice guests will be able to enjoy foods that respect the land and nourish the body. Created by Chef Johl Whiteduck Ringuette
11 a.m. – 6 p.m. (Friday to Sunday)
3115 Conservation Rd
Milton, ON

Trafalgar Township Heritage Day @ Palermo School House
Heritage and artifact displays, Indigenous history display, historical crafts, games and a book sale. Highlight is Palermo Pioneer Cemetery Walking Tour.
10 a.m. – 2 p.m.
2431 Dundas Street West, Oakville, ON

Harvest Festival @ Bronte Creek Provincial Park
Pick and carve your own pumpkin, enjoy kettle corn, hot dogs, fresh corn, apple cider and apple blossoms, tour a turn-of-the-century farmhouse, see apple cider pressing demonstrations, saw a souvenir medallion with a four foot long cross cut saw, hop on our complimentary wagon ride
10 a.m.  – 4 p.m.
1219 Burloak Drive, Oakville, ON

Sunday September 25th

Appleby Line Street Festival @ Appleby & New Street
The Appleby Line Street Festival brings families and neighbourhoods together by making the streets come alive with activity
1 p.m. – 5 p.m.
On Appleby, btw New and Fairview
Burlington, ON

Sunday Pickup Volleyball @ Haber Recreation Centre
4 courts maximum 48 players
7 p.m.
3040 Tim Dobbie Dr., Burlington, ON

Yankees vs Red Socks @ Yankee Stadium
Play Ball ! 
7 p.m. – 11 p.m.
Live Stream on Apple TV+
Bronx, NY

Loosen The Load With These 3 Simple Moving Tips

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Click Here to see more photos

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Has the last little duckling left the nest for University this year? If so, it might be time to make a plan.   Click Here  for a complimentary home evaluation. It might just be the tweek you need to get started. 

Have a great weekend everyone! Join my Meet Me In Oakville   Facebook Group  where we can talk about all the fun things to do In and Around Oakville

P.S. If you’d like me to list your event here just call, text, or email 905-399-7229 

Claudia Chopik

Claudia Chopik

Hi, there! I’m Claudia, the founder of Meet Me In Oakville – A strong tribe of Oakville residents who get weekly information about the best events, restaurants, shopping, activities, and real estate In and Around Oakville, Ontario.