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May 2025
May 2025
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Events List

(24 Results Found)
May 4, 2025 to May 31, 2025
Community Events
Public Meetings
Festivals and Events
Arts and Culture
Nature and Recreation
Sporting Events
MAY
4

I'm in Love with Your Sister

Sunday, May 4, 2025 - 2:00 pm
Theatre Orangeville, 87 Broadway, Orangeville, ON
I’m in Love With Your Sister starts out like any other love story, until an awkward fork in the road that sets off a chain of events that finds Kevin questioning where (or with whom) his life may actually take him. One loving and attentive boyfriend, two wildly different sisters, a little bit of awkwardness - most comedies ...
MAY
7

I'm in Love with Your Sister

Wednesday, May 7, 2025 - 2:00 pm
Theatre Orangeville, 87 Broadway, Orangeville, ON
I’m in Love With Your Sister starts out like any other love story, until an awkward fork in the road that sets off a chain of events that finds Kevin questioning where (or with whom) his life may actually take him. One loving and attentive boyfriend, two wildly different sisters, a little bit of awkwardness - most comedies ...
MAY
8

I'm in Love with Your Sister

Thursday, May 8, 2025 - 7:30 pm
Theatre Orangeville, 87 Broadway, Orangeville, ON
I’m in Love With Your Sister starts out like any other love story, until an awkward fork in the road that sets off a chain of events that finds Kevin questioning where (or with whom) his life may actually take him. One loving and attentive boyfriend, two wildly different sisters, a little bit of awkwardness - most comedies ...
MAY
9

I'm in Love with Your Sister

Friday, May 9, 2025 - 7:30 pm
Theatre Orangeville, 87 Broadway, Orangeville, ON
I’m in Love With Your Sister starts out like any other love story, until an awkward fork in the road that sets off a chain of events that finds Kevin questioning where (or with whom) his life may actually take him. One loving and attentive boyfriend, two wildly different sisters, a little bit of awkwardness - most comedies ...
MAY
10

Dufferin Hi-Land Bruce Trail Club: Two Day End-to-End Hike

Saturday, May 10, 2025 - 7:00 am
Dufferin Hi-Land Bruce Trail Club P.O. Box 698 Alliston, ON L9R 1V9
Registration is now open for this super popular hike that will earn you the Red Trillium Badge upon completing the Dufferin section of the Bruce Trail in two days, May 10 and 11. Join us for a fun weekend of hills and valleys, hiking a total of 56 km through the Boyne Valley, Kilgorie, Honeywood Ridge, Black Bank and Lave ...
MAY
10

Orangeville Farmers' Market

Saturday, May 10, 2025 - 8:00 am to 1:00 pm
Beside Town Hall - 87 Broadway, Orangeville, ON
The Orangeville Farmers' Market offers the best in fresh produce, fruits, locally raised meats, fish, flowers, home baked goods and unique artisan crafts. Located directly beside Town Hall on Second Street, the market features free weekly draws, live entertainment, special events, and activities for children.Visit downtowno ...
MAY
10

Orangeville ComiCon

Saturday, May 10, 2025 - 10:00 am to 3:00 pm
Orangeville Curling Club, 76 Fifth Avenue, Orangeville, ON
Enjoy a day of fan culture at the Orangeville ComiCon, hosted by POP Culture Canada. The event will offer the opportunity to meet with artists and authors, and shop from a wide range of vendors selling comic books, new and vintage toys, jewelry, DVD's, anime, manga, prints, and more! Attendees are encouraged to join in the ...
MAY
10

GCW Live Wrestling!

Saturday, May 10, 2025 - 6:00 pm to 8:30 pm
Orangeville Curling Club, 76 Fifth Avenue, Orangeville, ON
Wrestling superstars from all over Ontario will be live. Stick around for intermission and meet your favourite superstars!
MAY
10

I'm in Love with Your Sister

Saturday, May 10, 2025 - 7:30 pm
Theatre Orangeville, 87 Broadway, Orangeville, ON
I’m in Love With Your Sister starts out like any other love story, until an awkward fork in the road that sets off a chain of events that finds Kevin questioning where (or with whom) his life may actually take him. One loving and attentive boyfriend, two wildly different sisters, a little bit of awkwardness - most comedies ...
MAY
11

Dufferin Hi-Land Bruce Trail Club: Two Day End-to-End Hike

Sunday, May 11, 2025 - 7:00 am
Dufferin Hi-Land Bruce Trail Club P.O. Box 698 Alliston, ON L9R 1V9
Registration is now open for this super popular hike that will earn you the Red Trillium Badge upon completing the Dufferin section of the Bruce Trail in two days, May 10 and 11. Join us for a fun weekend of hills and valleys, hiking a total of 56 km through the Boyne Valley, Kilgorie, Honeywood Ridge, Black Bank and Lave ...
MAY
11

I'm in Love with Your Sister

Sunday, May 11, 2025 - 2:00 pm
Theatre Orangeville, 87 Broadway, Orangeville, ON
I’m in Love With Your Sister starts out like any other love story, until an awkward fork in the road that sets off a chain of events that finds Kevin questioning where (or with whom) his life may actually take him. One loving and attentive boyfriend, two wildly different sisters, a little bit of awkwardness - most comedies ...
MAY
13

Orangeville and District Horticultural Monthly Meeting

Tuesday, May 13, 2025 - 6:30 pm to 8:30 pm
26 Bythia St
Please welcome our guest speaker tonight, Sean James as he talks about "Xeriscaping". Our water is precious. Learn how to use it wisely in our gardens. Free parking, guests are welcome, draw prizes, bring a mug for refreshments. There is also a flower show tonight.
MAY
14

I'm in Love with Your Sister

Wednesday, May 14, 2025 - 2:00 pm
Theatre Orangeville, 87 Broadway, Orangeville, ON
I’m in Love With Your Sister starts out like any other love story, until an awkward fork in the road that sets off a chain of events that finds Kevin questioning where (or with whom) his life may actually take him. One loving and attentive boyfriend, two wildly different sisters, a little bit of awkwardness - most comedies ...
MAY
15

I'm in Love with Your Sister

Thursday, May 15, 2025 - 11:00 am
Theatre Orangeville, 87 Broadway, Orangeville, ON
I’m in Love With Your Sister starts out like any other love story, until an awkward fork in the road that sets off a chain of events that finds Kevin questioning where (or with whom) his life may actually take him. One loving and attentive boyfriend, two wildly different sisters, a little bit of awkwardness - most comedies ...
MAY
15

I'm in Love with Your Sister

Thursday, May 15, 2025 - 7:30 pm
Theatre Orangeville, 87 Broadway, Orangeville, ON
I’m in Love With Your Sister starts out like any other love story, until an awkward fork in the road that sets off a chain of events that finds Kevin questioning where (or with whom) his life may actually take him. One loving and attentive boyfriend, two wildly different sisters, a little bit of awkwardness - most comedies ...
MAY
16

I'm in Love with Your Sister

Friday, May 16, 2025 - 7:30 pm
Theatre Orangeville, 87 Broadway, Orangeville, ON
I’m in Love With Your Sister starts out like any other love story, until an awkward fork in the road that sets off a chain of events that finds Kevin questioning where (or with whom) his life may actually take him. One loving and attentive boyfriend, two wildly different sisters, a little bit of awkwardness - most comedies ...
MAY
17

Orangeville Farmers' Market

Saturday, May 17, 2025 - 8:00 am to 1:00 pm
Beside Town Hall - 87 Broadway, Orangeville, ON
The Orangeville Farmers' Market offers the best in fresh produce, fruits, locally raised meats, fish, flowers, home baked goods and unique artisan crafts. Located directly beside Town Hall on Second Street, the market features free weekly draws, live entertainment, special events, and activities for children.Visit downtowno ...
MAY
17

I'm in Love with Your Sister

Saturday, May 17, 2025 - 7:30 pm
Theatre Orangeville, 87 Broadway, Orangeville, ON
I’m in Love With Your Sister starts out like any other love story, until an awkward fork in the road that sets off a chain of events that finds Kevin questioning where (or with whom) his life may actually take him. One loving and attentive boyfriend, two wildly different sisters, a little bit of awkwardness - most comedies ...
MAY
18

I'm in Love with Your Sister

Sunday, May 18, 2025 - 2:00 pm
Theatre Orangeville, 87 Broadway, Orangeville, ON
I’m in Love With Your Sister starts out like any other love story, until an awkward fork in the road that sets off a chain of events that finds Kevin questioning where (or with whom) his life may actually take him. One loving and attentive boyfriend, two wildly different sisters, a little bit of awkwardness - most comedies ...
MAY
24

Orangeville Farmers' Market

Saturday, May 24, 2025 - 8:00 am to 1:00 pm
Beside Town Hall - 87 Broadway, Orangeville, ON
The Orangeville Farmers' Market offers the best in fresh produce, fruits, locally raised meats, fish, flowers, home baked goods and unique artisan crafts. Located directly beside Town Hall on Second Street, the market features free weekly draws, live entertainment, special events, and activities for children.Visit downtowno ...
MAY
28

Authors on Stage Robert MacFarlane

Wednesday, May 28, 2025 - 7:00 pm
Theatre Orangeville, 87 Broadway, Orangeville, ON
Join us for another Authors on Stage event in partnership with our good friends at BookLore. An evening with Robert MacFarlane, in discussion with moderator Bernadette Hardaker, we discuss his book, Is A River Alive? ‍From the publisher: ROBERT MACFARLANE is the author of prize-winning and bestselling books about nature ...
MAY
30

Orangeville Blues & Jazz Festival

Friday, May 30, 2025 - 5:00 pm
11 Second Street, Orangeville, ON
The popular Orangeville Blues & Jazz Festival will feature acts on three stages, and in local pubs, restaurants, and event venues around town. The festival opens on Friday night with the popular Blues Cruise on Broadway which will include over 250 classic cars and several bands performing on Broadway. Throughout the weekend ...
MAY
31

Orangeville Farmers' Market

Saturday, May 31, 2025 - 8:00 am to 1:00 pm
Beside Town Hall - 87 Broadway, Orangeville, ON
The Orangeville Farmers' Market offers the best in fresh produce, fruits, locally raised meats, fish, flowers, home baked goods and unique artisan crafts. Located directly beside Town Hall on Second Street, the market features free weekly draws, live entertainment, special events, and activities for children.Visit downtowno ...
MAY
31

Orangeville Blues & Jazz Festival

Saturday, May 31, 2025 - 12:30 pm
11 Second Street, Orangeville, ON
The popular Orangeville Blues & Jazz Festival will feature acts on three stages, and in local pubs, restaurants, and event venues around town. The festival opens on Friday night with the popular Blues Cruise on Broadway which will include over 250 classic cars and several bands performing on Broadway. Throughout the weekend ...
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