Window Art Stroll & Contest


The Window Art Stroll & Contest showcases the amazing talent in Connecticut and helps professional artists promote their businesses, products and/or services by bringing art outdoors, directly to the public in a safe and responsible manner while creating a welcoming and vibrant downtown community. Artists will paint their designs at 30 locations on Saturday, May 15 beginning at 10:00am.


Enjoy a pleasant stroll through three districts in historic downtown New Haven — Broadway, Chapel and Whitney-Audubon. Vote for your favorite design and you will be entered to win 1 of 10 $50 gift cards to retailers & restaurants — L.L.Bean, Tarry Lodge, lululemon, idiom Boutique, Shake Shack, Raggs for Men & Women, Walker-Loden, Katalina’s Bakery, Urban Outfitters or J.Crew!


The online people’s choice voting form will be live from May 15 – June 27, 2021.



Printed Event Guides with walking maps will be available at all participating merchants beginning on May 15.

View the high resolution 17″ x 11″ Event Guide with retail and restaurant directory, click here!


Prizes include $500 to L.L.Bean New Haven for first place, $250 to Patagonia New Haven for second place, $150 to Sneaker Junkies for third place, $100 to J.Crew for Best Summer Theme on Broadway, $100 to Raggs for Men & Women for Best Summer Theme on Chapel Street and $100 to Walker-Loden for Best Summer Theme on Whitney Avenue. Winners are chosen via people’s choice and will be announced during the week of June 28.


The Shops at Yale and Whitney-Audubon Retail & Arts District organize both paid projects like our Mural Demonstration Series on Broadway Island and the 40’ outdoor mural installation at 44 Whitney Avenue by Ben Keller, and contests such as the Window Art Stroll & Contest. Contests are usually larger in scale, involve temporary art from many artists and include a people’s choice voting component with tiered prizes, like our popular New Haven Chalk Art Festival that attracts more than 80 artists from all over the region. This event is a contest with a people’s choice voting system. 


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