Jen Adams’ dog trainer likes to say that owners should treat their dogs like purses; they shouldn’t walk away from them. With that in mind, Adams dressed her mastiff, Maggie, like a purse for Halloween.

“My dogs dress themselves,” Adams said. “They happen to like clothes.” 

Monday night was “Howl-o-Ween” at Wareham Crossing as members of the Wareham Pack Walkers took their costumed canines “trick-or-treating” through the shopping center. 

“We like takin’ walks, and it’s fun to have them dressed up,” said Jennifer Cipriani, a dog trainer and founder of Wareham Pack Walkers. “Something different. It’s a little fun for the folks at home who don’t have kids or don’t have trick or treaters.”

Cipriani founded the Wareham Pack Walkers in 2016 to teach dogs obedience and socialization. The purpose of the four-legged Halloween parade was not only to delight shoppers and show off adorable costumes, but teach the dogs to adjust to large crowds.

“Going in and out of the shops, and the sound of the shopping carriages, is part of getting her to relax in social situations,” Karen Midttun said about her golden retriever Willow.

It didn’t take long for Midttun to make Willow’s fairy princess costume.

“I just took her harness and I stitched a tutu and wings to it,” she said, “and I just tacked on the fairy lights.”

Hanzo and Kiwi won the costume contest. Their owner, Michele Simmons, dressed them as a devil and angel, respectively. 

“It definitely reflects their personalities,” she said. [Hanzo] is a good boy, but he’s a little devil, huh, buddy?”

First prize was a raffle basket donated by Black Dog Outlet, which contained a hat, a toy, treats and a bandana. 

Paula Nord’s goldendoodle Izzy, who was dressed as a lion, came in second place. She won a few toys and some dehydrated fish. 

Nord said that Izzy likes to think she’s a lion, but she’s really a “snacking couch potato.”

“We found the costume online, and it was something different for her,” she said. “Want a treat? You have to wait. Can you wait? Thank you. I know…”

Leslie O’Brien, walking with her dog Bambi, was excited to see all the dogs in costume.

“Bambi doesn’t keep anything on too good,” she said. “She loses half of [her costumes] before we finish our walk.”

Luna, Jennifer Haley’s German shepherd, wore a shirt reading “I ate my costume.”

“We couldn’t find anything else to fit her,” Haley said.

Cipriani said that her dog is “kind of a jerk” and really does eat her costumes.

“Each dog has their own personality,” she said. “Most of the dogs do okay. The ones that don’t have costumes tonight… they don’t do okay.”