Montgomery's ANNUAL STREET FESTIVAL
Chalk the Block &
Montgomery Street Market
Montgomery's Annual street festival
Chalk the Block &
Montgomery Street Market
On June 27, 2026, Bowness Road between 44th and 46th Streets transformed into Montgomery’s biggest canvas yet for the second annual Chalk the Block Festival. This year’s theme, “Chalk What Makes You Smile,” invited artists, families, and neighbours to fill our streets with joy, creativity, and moments that spark happiness — big or small.
From playful doodles to heartfelt messages, every chalked square became a reminder of what brings our community together. Thousands of Montgomery residents and visitors walked the block, browsed local vendors, and soaked in the sunshine (well — most of it) alongside live entertainment and a beer garden hosted by Brewsmith Brewing.
Thank you to everyone who came out, chalked up, and made this year’s festival one to remember.
Chalk the Block 2026 Winners
Celebrating the imagination, talent, and dedication of this year’s top chalk artists.
Elementary Solo Ages 5-11
#27 – Samyuktha V.
#14 – Mackenzie
Elementary Teams Ages 5-11
#39 – Farrah & Edelyn
#11 – Owen & Frankie
Middle/High School Ages 12-18
#24 – Annalise – People’s Choice Winner
#25 – Jensen
Adult Solo: Ages 18 and Up
#43 – Akmaral
#32 – Vanessa
Adult Teams: Ages 18 and Up
#52 – Yeganeh & Parvin
#47 – Sheena & Team
2026 CHALK THE BLOCK PARTICIPANTS
1
Amy T.
Elementary Solo Ages 5-11
2
Please email Us!
Elementary Solo Ages 5-11
3
Olivia H.
Middle School Solo Ages 12-18
4
Ashlynn R.
Elementary Solo Ages 5-11
5
Ella M.
Elementary Solo Ages 5-11
6
Zoe M.
Elementary Solo Ages 5-11
7
Eliana
Elementary Solo Ages 5-11
8
Eliana, Ammara, Ivy
Elementary Teams Ages 5-11
9
June Strap & Vaughn Lord
Elementary Teams Ages 5-11
10
Alix Lord
Elementary Solo Ages 5-11
11
Owen & Frankie
Elementary Teams Ages 5-11
12
Ave & Max D.
Elementary Teams Ages 5-11
13
Colin
Elementary Solo Ages 5-11
14
Mackenzie
Elementary Solo Ages 5-11
15
Alice
Elementary Solo Ages 5-11
16
Sarah
Elementary Solo Ages 5-11
17
Svea M.
Middle/High School Ages 12-18
18
Skyler M.
Middle/High School Ages 12-18
19
Andrew & Team
Adult Teams 18+
21
Marlo B.
Middle/High School Ages 12-18
22
Alayna V.
Middle/High School Ages 12-18
23
Serene
Middle/High School Ages 12-18
24
Annalise J.
Middle/High School Ages 12-18
25
Jensen A.
Middle/High School Ages 12-18
26
Sky P.
Adult Solo: Ages 18 and Up
27
Samyuktha V.
Adult Solo: Ages 18 and Up
28
Karylle A.
Adult Solo: Ages 18 and Up
29
Please Email Us!
Adult Solo: Ages 18 and Up
30
Lydia K.
Adult Solo: Ages 18 and Up
31
Mai & Kevin
Adult Teams: Ages 18 and Up
32
Vanessa M.
Adult Solo: Ages 18 and Up
33
Tammy M.
Adult Solo: Ages 18 and Up
34
Sandra M.
Adult Solo: Ages 18 and Up
35
Please Email Us
Adult Solo: Ages 18 and Up
36
Chris, Ara & Wendy
Adult Teams: Ages 18 and Up
37
Hazem & Valentina
Adult Teams: Ages 18 and Up
38
Satoko & Allisha
Adult Teams: Ages 18 and Up
39
Farrah & Edelyn
Elementary Teams Ages 5-11
40
Ty P.
Adult Solo: Ages 18 and Up
41
Tamara S.
Adult Solo: Ages 18 and Up
42
Azka A.
Adult Solo: Ages 18 and Up
43
Akmaral S.
Adult Solo: Ages 18 and Up
44
Azka
Adult Solo: Ages 18 and Up
45
Nicole I.
Adult Solo: Ages 18 and Up
46
Rozzie L.
Adult Solo: Ages 18 and Up
47
Sheena & Team
Adult Teams: Ages 18 and Up
48
Crystal & Team
Adult Teams: Ages 18 and Up
49
Jade & Team
Adult Teams: Ages 18 and Up
50
Please email Us!
Adult Teams: Ages 18 and Up
51
Please email Us!
Adult Teams: Ages 18 and Up
52
Yeganeh & Parvin
Adult Teams: Ages 18 and Up
54
Gibson & Team
Adult Teams: Ages 18 and Up
55
Stephanie & Team
Adult Teams: Ages 18 and Up
57
Karolina K.
Elementary Solo Ages 5-11
GET NOTIFIED FOR
CHALK THE BLOCK 2027
We had an amazing turn out for artists and vendors with over 40+ on our waitlist + day of requests. Put your name on our mailing list to be notified when details are released for 2027.