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Photos courtesy of Waggin’ Trails
Waggin’ Trails
Dog hair on the floor. Slobbery kiss marks on the windows. Tails wagging like crazy. That’s not chaos at Waggin’ Trails, it’s HOME. For founder Lynsee Openshaw, creating a business like this was a lifelong dream waiting to happen. After years in healthcare and dentistry, she made a bold switch and followed her heart straight to the dogs. Growing up in Montana, she spent much of her high school life caring for family and friends’ pets, a trusted responsibility that never really left her. In March 2024, she officially turned that passion into a career, swapping dental tools for leashes, muddy paw prints, and an entire bus full of dogs. And yes, that bus is real. Affectionately known as the “Wag Wagon,” it’s bright yellow and filled with happy pups heading off to adventures or home after their own little vacations.
Waggin’ Trails began with group dog hikes, giving dogs a chance to run free, burn off energy, and meet friends along the way. It didn’t take long before customers started asking for more, whether that was boarding in a homey environment, late-night drop-ins to feed dinner, or simple dog walks. Lynsee’s answer was always yes, and the result is a service that feels far more personal than a traditional, crowded facility. The atmosphere might look like muddy paws on the floor and slobbery kiss marks on the windows, but the vibe is all wagging tails, sunshine naps, and dogs who come home happily worn out.
Treats quickly became the cherry on top of everything Waggin’ Trails offers. Lynsee had always made homemade snacks for her own pups, so it was only natural to add them to her growing business. That’s how Waggin’ Trails Pup Bakery was born, a line of small-batch, preservative-free goodies now making their way to local farmers markets, coffee shops, stores around Billings, and even online through waggintrails.dog. Dogs are “obsessed,” as one customer put it, and even cats are now getting in on the action with a line of feline treats in the works. To top it off, Waggin’ Trails partners with local coffee shops by donating treats for their pup cups, a community connection that’s been a win-win for dogs and owners alike.
At the heart of it all, Lynsee hopes her clients feel peace. As a dog mom herself, she knows how hard it is to trust someone else with your pets. Hearing from owners who say they enjoyed their vacation worry-free because their pup was safe and happy at Waggin’ Trails is the best reward. The tired, well-behaved dogs who return home after play and adventure are proof that the system works.
Billings has been quick to show its support, and Lynsee says the encouragement of the community means everything. Starting a business from scratch isn’t easy, but every bag of treats purchased or pup dropped off for boarding fuels her dream and strengthens her belief in shopping local. She hopes to continue expanding, hiring more animal lovers to help with hikes and drop-ins, and eventually finding a larger space for dogs to roam while still keeping that warm, home-away-from-home feel.
Until then, keep an eye out for the Wag Wagon around town, full of grinning pups on their way to the next adventure. For Lynsee and the dogs she cares for, every trail is a new chance to wag.
