New friends and old snuggled up to say "hi." (Hanbit Kwon for Billy Penn)

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On Sunday, dozens of dogs and their people gathered for the 4th annual Chestnut Hill Community Association‘s Halloween Pet Costume Parade, part of “Halloween on the Hill.” 

A ton of pets came out for the Halloween Pet Parade in Chestnut Hill. (Hanbit Kwon for Billy Penn)

The parade kicked off near the corner of East Evergreen and Germantown avenues and then ambled down Germantown at an unhurried pace to Buckley Park, at the corner of Germantown Avenue and East Hartwell Lane. 

A pair of pups doubles the fun during Chestnut Hill’s Halloween Pet Parade. (Hanbit Kwon for Billy Penn)

Lead dog Lola often stopped to sniff out an interesting odor on the wind. Many of the dogs participating appeared oblivious of their appeal, unaware that they were actually the main attraction of this adorable procession. 

Tilly, dressed as a bikini-ed mermaid alongside her mermaid mom Amanda won the category of “Funniest” this year. (Hanbit Kwon for Billy Penn)

The parade first began in 2023, post-COVID, explained Anne McNiff, executive director of the Chestnut Hill Community Association. The association staff pitched a Halloween event that would bring neighbors together and lift everyone’s spirits. 

Sally, pictured here with her person, took home the prize for “Cutest” this year for her Where’s Waldo costume, marking a multi-year winning streak for this adorable Doodle. (Hanbit Kwon for Billy Penn)

As Will Standish, the association’s Membership and Administrative coordinator explained, the annual Halloween Pet Costume Parade is a perfect opportunity for the Chestnut Hill community “to do something kind of silly, and celebrate the season.” 

Chestnut Hill has a history of residents with a deep connection to their pets. The Association once offered pet memberships to the Chestnut Hill Community Association, listing the animal’s name on the human member’s profile and sending treats in the mail. 

Many pups were not too shy to pose for photos. (Hanbit Kwon for Billy Penn)

McNiff, who moved to the area from the Santa Barbara, California, area, said she sees every kind of dog in Chestnut Hill, from “little fancy dogs” to “big rescues.” This year’s parade sponsor Doggie Style Pets has adoptable rescue dogs in its Chestnut Hill location at all times. 

Cyrus was recently surrendered to the city shelter after his owner moved away and left him with a cousin. The cousin then moved to a place with pet restrictions and Cyrus was left unhoused again. But, no bother, the Chestnut Hill community has been showing up for Cyrus in a big way. 

This pooch is walking down Germantown Avenue like it’s his runway. (Hanbit Kwon for Billy Penn)

Store employee Jesse Bryant said that neighbor volunteers signed up and then showed up to walk Cyrus nine times last Sunday alone in the space of a single five-hour shift. That’s at least one walk just about every 30 minutes! 

Cyrus and Jesse Bryant take a mid-shift break to cuddle. (Hanbit Kwon for Billy Penn)

While many spectators came out specifically to enjoy the pet parade, other onlookers were pulled in by the unexpected pleasure of seeing so many pups in such a wide array of outfits. 

Nicolle Blackmon highlights her pup Bentley Ashton’s dinosaur getup while her daughter Layla looks on. (Hanbit Kwon for Billy Penn)

The event was timed to end around the beginning of the Chestnut Hill Business District’s annual trick-or-treating event for kids, and Germantown Avenue was soon overflowing with puppies and families. 

Cruella de Vil has 101 problems, but spots ain’t one. (Hanbit Kwon for Billy Penn)

As McNiff told friends and neighbors beforehand, “If the world is getting you down, come out at 12:30.”