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Guided Dog Hiking Adventures
in Colorado Springs

Trail adventures that exercise the body and engage the mind.

About

The Story Behind The Adventures

Dogs have always been a central part of my life, including working with behaviorally complex dogs.

Hi, I'm Diana, and I’ve spent a lifetime with dogs, learning to understand their personalities, needs, and behaviors. Without formal training, I’ve rescued, rehabilitated, and rehomed dogs with challenging behaviors, relying on patience, intuition, and connection to help them thrive.

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One of my most meaningful rescues was Little Wolf, a Cairn Terrier who came to me in crisis. She had been taken in by a woman after her friend passed, but she was reactive to every person and animal, relentlessly trying to attack her cat, and generally unpredictable. The lady urgently needed to rehome her, and knew a shelter would likely deem her unadoptable as she wouldn't hesitate to bite. Little Wolf was my most challenging case, but with time, patience, and care, she transformed into a sweet, engaging dog, even enjoying biscuit massages from a friend’s cat. Eventually, I found her a loving home on ten acres with a couple who had recently lost their dog “Toto” and were overjoyed to welcome her.

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I recently realized how much I missed spending my days helping and connecting with dogs. Looking to transition out of my 9-5, I decided to turn my love, experience, and intuitive understanding of dogs into my own small business. 

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The Mission

Pawsitive Outdoor Adventures exists to give dogs safe, structured outdoor experiences that promote exercise, enrichment, confidence, and well-being while supporting stronger relationships between dogs and their people.

Explore Adventures

Adventures

All adventures are tailored to your dog’s energy, behavior, and comfort level.

Insured For Pets In My Care

Puppy Playing Outdoors
Stay & Play
1 HOUR @ $30

This is for dogs who are happiest at home or need extra attention in their own space. Includes yard play, mental enrichment, basic training, potty breaks, and plenty of companionship. Perfect for puppies, seniors, or dogs who prefer familiar surroundings. Additional dogs at $15 each. 

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Adventure Hike

2 HOURS @ $50

A longer trek for active dogs who need more than a short stroll. Great for building endurance and burning energy. It includes water, treats, breaks as needed, and all the affection they want. Dogs are encouraged to wear packs when appropriate. Additional same household dogs at $25 each.

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Half Day Adventure

4 Hours @ $80

Perfect for high-energy dogs! Includes a hike, playtime, and plenty of breaks, providing both mental and physical stimulation. Fresh water and treats are provided, with affection and attention tailored to your dog’s needs. Additional same household dogs: $40 each.

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Full Day Adventure

8 HOURS @ $130

Immerses dogs in a full day of outdoor excitement, exercise, and enrichment. Dogs may experience hiking, swimming, park visits, and exploration tailored to their energy, personality, and comfort level.  Additional same household dogs at $65 each.

FAQs

FAQs

Common Questions

How does scheduling/grouping work?

Each weekend I plan adventures for the following one to two weeks. When scheduling, I consider dogs

who have completed their Meet & Greet and requested an adventure, the type of outing requested, each dog’s temperament and interests, client location if transportation is involved, and weather and trail conditions.

Will I need to drop my dog off at a designated location?

Drop-off windows and general meet-up locations will be provided for each adventure. To keep outings running smoothly, dogs should arrive within the scheduled window so the group can depart on time. Adventures leave promptly at the listed departure time, and late arrivals may miss the outing and still be subject to the full charge.

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For added convenience, transportation or alternate meet-up arrangements may be available depending on location, scheduling, and the needs of the client. An additional fee may apply.

What should my dog bring?

Dogs should arrive wearing a properly fitted collar, harness (or tool of choice) and leash. If your dog has special treats, dietary restrictions, or requires medication, please include those with clear instructions. Pawsitive Outdoor Adventures provides fresh water, bowls, treats (unless otherwise requested), waste bags, and a pet first aid kit so your dog can enjoy a safe and comfortable adventure.

Will I need to drop my dog off at a designated location?

Is every dog eligible for full day adventures?

Full day adventures are reserved for dogs who are established with Pawsitive Outdoor Adventures. This ensures they’re fully comfortable before joining a longer day on the trail.

Dogs should arrive wearing a properly fitted collar or harness and leash. If your dog has special treats, dietary restrictions, or requires medication, please include those with clear instructions.

Pawsitive Outdoor Adventures provides fresh water, bowls, treats (unless otherwise requested), waste bags, and a pet first aid kit so your dog can enjoy a safe and comfortable adventure.

Is every dog eligible for full day adventures?

What if my dog has behavior challenges?

Adventures are primarily meant for dogs who have a sweet and social temperament. That said, dogs with behavioral challenges may still be eligible for adventures. In most cases, we begin with solo Stay & Play sessions or shorter 2-hour adventures to assess behavior and build trail manners before progressing to longer or group outings.

Full day adventures are reserved for dogs who are well established with Pawsitive Outdoor Adventures. This helps ensure your dog is comfortable with the routine, environment, and group dynamics (if applicable) before participating in a longer day on the trail.

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