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09
May

Pickering Petapolooza

06:00 AM | Canada, Ontario - Esplanade Park

Petapolooza is an annual event that brings together pet owners and enthusiasts within our community. It gives our community the opportunity to meet industry professionals, rescue groups, and others in the pet industry.

Last years  Petapolooza Pet Festival saw a record breaking attendance of over 4,500 people and brought in $36,000 ($11,729.45 in donations from the day of).

Petapolooza is Animal Services largest fundraiser with all proceeds going towards building Pickering a permanent animal shelter and/or for the day to day care of animals housed at the shelter, including unforeseen medical costs.

Yes
Exhibits & Expos
24
May

Jack de Keyzer

02:00 PM | Canada, Ontario - The Back Alley Bar & Grill
Sunday Afternoon Blues Series presents Jack de Keyzer 2X JUNO Award Winner 7X Maple Blues Awards Winner
No
Concerts & Shows
30
May

Kites in Clifford

10:00 AM | Canada, Ontario - Clifford Rotary Park

A Partnership with Clifford connects and the Minto & District Lions Club

This spring, Clifford’s skies will come alive.

Kite flyers from across the region will bring giant, breathtaking kites to our community for a day filled with colour, connection, and fresh-air fun.

The event will also feature a Vendor's Market, kids' activities, food trucks, and more. Bring your own kite to fly alongside the professionals!

Yes
Sport Events
30
May

Oshawa Indigenous Cultural Celebration

12:00 PM | Canada, Ontario - Ed Broadbent Waterfront Park

Come celebrate the beginning of National Indigenous History Month in Canada with a variety of energetic performances, storytelling, spoken word artists, traditional dancing, hand drumming, and interactive workshops led by First Nations, Inuit, and Métis presenters and storytellers.

The Indigenous Cultural Celebration in Oshawa is a powerful event that honours and celebrates the rich heritage of First Nations, Métis, and Inuit peoples. Held in June to kick off Indigenous History Month, the event features traditional teachings, presentations, and interactive activities, including water and strawberry teachings by Elders and drumming sessions. Visitors will enjoy Indigenous food and vendors while learning from local Indigenous leaders and presenters. Held at the culturally significant Ed Broadbent Park, this event fosters education, cultural awareness, and community connection, offering a meaningful opportunity for reconciliation and celebration of Indigenous traditions.

Yes
Cultural Events
30
May

Classical Spring: Sonatas and Miniatures

03:30 PM | Canada, Ontario - Grace United Church
The Festival Duo with violinist Sadie Fields and pianist Ken Gee return to Grace United Church for their annual spring concert in Thornbury. Beethoven “Spring” Sonata for piano & violin No. 5 in F major, Op. 24; Lili Boulanger Two Pieces for violin & piano (Nocturne, Cortège); Mozart Sonata for piano & violin No. 21 in E minor, K. 304; Tchaikovsky Souvenir d’un lieu cher (Méditation, Scherzo, Mélodie). Saturday May 30 at 3:30 pm at Grace United Church, 140 Bruce St S, Thornbury
Concerts & Shows
21
Jun

29th Annual Father’s Day Smoke & Steam Show

06:00 AM | Canada, Ontario - Lang Pioneer Village Museum
Yes
Events
21
Jun

Stouffville Main Street 5K

09:39 AM | Canada, Ontario - Memorial Park - Stouffville
We look forward to welcoming competitive and recreational runners and walkers alike for our 4th annual Stouffville Main Street 5K and Kids 1K Dash benefitting the Markham Stouffville Hospital Foundation.
Sport Events
01
Jul

Pickering Canada Day

08:00 AM | Canada, Ontario - Esplanade Park

Celebrate Canada Day 2026 in Pickering!

Join us for a full day of celebration featuring live entertainment, a variety of food vendors, and family-friendly activities as we come together to honour Canada’s birthday. Daytime and evening programming will offer something for everyone, from lively performances to festive community experiences.

Two venues:

12:00 pm - 5:00 pm
Esplanade Park

7:00 pm - 10:00 pm
Kinsmen Park

Yes
Cultural Events
05
Jul

Town of Midland Music in the Park

06:00 PM | Canada, Ontario - Midland, Ontario

Join us for free family-friendly concerts all summer at Midland's Little Lake Park!

Yes
Concerts & Shows
10
Jul

Concerts in the Park

03:00 AM | - Mill Pond Park Richmond Hill
Please ensure dogs are on a leash
Concerts & Shows
12
Jul

29th Annual Transportation Day Car & Motorcycle Show

06:00 AM | Canada, Ontario - Lang Pioneer Village Museum
Yes
Events
16
Jul

Concerts in the Park

11:00 PM | - Mill Pond Park Richmond Hill
Please ensure dogs are on a leash
Concerts & Shows
27
Sep

Applefest

06:00 PM | Canada, Ontario - Lang Pioneer Village Museum
Yes
Events
23
Oct

Spooky All Hallows' Eve

02:00 AM | Canada, Ontario - Lang Pioneer Village Museum
Yes
Holiday & Special Events
11
Nov

City of Oshawa: Remembrance Day

05:30 AM | Canada, Ontario - Memorial Park - Oshawa
Other Events
21
Nov

Pickering Santa Claus Parade

05:00 AM | - PIckering Santa Clause Parade Route

Santa Claus is coming to Pickering! With extravagant floats from Pickering businesses and community groups, marching bands, and Santa Claus himself, the Santa Claus Parade is the spectacle to kick off everyone’s holiday season. The parade will begin at Dixie and Glenanna and end in Pickering’s City Centre.

yes
Holiday & Special Events
21
Nov

Christmas Bazaar & Raffle

02:00 PM | Canada, Ontario - Lang Pioneer Village Museum
Yes
Holiday & Special Events
06
Dec

Christmas by Candlelight

05:00 AM | Canada, Ontario - Lang Pioneer Village Museum
Yes
Holiday & Special Events
12
Dec

Santa's Village & Market

09:00 AM | Canada, Ontario - Heritage Garden Parks
Join us for a delightful holiday experience at the Annual Santa's Village & Market, a family-friendly event open to all ages. Immerse yourself in the heartwarming spirit of Christmas in the beautiful downtown of Essex Centre, in the middle of Essex County. Join us for a delightful holiday experience at the Annual Santa's Village & Market, a family-friendly event open to all ages. Immerse yourself in the heartwarming spirit of Christmas in the beautiful downtown of Essex Centre, in the middle of Essex County. This enchanting one-day event brings Christmas magic alive for everyone! Come and join in the festivities as you decorate scrumptious cookies and create magical reindeer food. Delight in the melodious tunes of live music while exploring a variety of food vendors offering freshly made donuts, cotton candy, and more. Discover a wide array of crafts and merchandise vendors, offering unique treasures for all. Don't forget to pay a visit to Santa's Workshop for a cherished photo opportunity and a special gift. And as the day unfolds, prepare to be amazed by our spectacular Santa Claus Parade, commencing at 6:30 PM! After the parade, come back into the village as the fun continues providing joy for all including grabbing that special Christmas gift before you head home! This is an event you wouldn't want to miss, a must-visit for families to kick off the Christmas holiday season with joy and wonder. Stay tuned for more updates as we approach the event date. Mark your calendars for the second Saturday of December each year in the picturesque downtown of Essex. You can find us conveniently located at the corner of Talbot and Victoria in the Heritage Gardens area, next to the Essex Historic Train Station!
Yes
Holiday & Special Events