The weather was perfect for Bayside’s 2nd Annual Howl-o-ween Doggie Costume Pageant. The Bayside Trail was transformed for a day thanks to a team effort led by Deirdre Paul who started things off with live music as “DD Sweet and the Bloody Eyeballs” featuring Mike Taylor on guitar and Nate Soule on bass. Pretty soon the stretch of trail behind Trader Joe’s was full of neighbors, kids, and dogs in costume.

And what costumes! Cashy showed up as a cowboy, Rudabaker was the Grinch, and Taterlily came as Buzz Lightyear. Bluey and Chase teamed up as the Two Bananas, Missy Mouse was there, and Betty took the prize for “cutest couple” with her human dressed in Victorian garb. Mr. Pemberton, last year’s purple octopus, came back as the Phantom of the Opera, and Radar went as the Spirit of Halloween. Prizes, courtesy of local pet stores Fish & Bone and Uncommon Paws, went out for Most Festive, Spookiest, Funniest, Cutest Couple, Best Behaved, and Most Original, and honestly every pup in the lineup deserved one. A special prize for bravery went to City Councilor Sarah Michniewicz’s cat, Dragon, who was dressed as a “purr-maid.”

There was plenty to do between the parade and the music. A pop-up dog park from Portland Parks & Recreation gave the pups room to run around, and the City Office of Sustainability made the games and activities possible. Two Fat Cats Bakery kept everyone fueled with sweet snacks, and plenty of free hot cider was there to keep us warm thanks to the Bayside Neighborhood Assocation and its donors.

Last year’s inaugural Howl-o-ween was a hit, and this year made it feel like a real neighborhood tradition. Part of the point has always been to bring some life to a part of Bayside that doesn’t usually have much going on, and a sunny Saturday full of costumed dogs, music, and neighbors did just that. Thanks to everyone who came out, to our neighborhood partners and benefactors, and to all the volunteers who helped set up and clean up. Special thanks to Deirdre and the Events Team for pulling it all together. If you’d like to help with next year’s pageant or any of our other gatherings, reach out to info@baysideportland.org.