Hiking Adventures

Cambridge • Boston • Brookline

As a more active, adventerous, alternative to traditional dog walking; our off-leash day hikes provide your pup plenty of exercise, freedom, and fulfillment.  Freedom to explore the trails, run through the fields, splash in the waters, and belong to a pack; then return home happy and fulfilled.

What We Offer

Day Hikes


Exercise and socialization are key for a happy, balanced, well-behaved dog. Our off-leash hikes are made up of small groups led by an experienced, knowledgeable pack leader. This allows your dog to run, play, and explore while learning proper dog behavior and social skills in their natural environment. At the end of the trip, your dog returns tired, happy, and fulfilled.

We offer morning and afternoon trips Monday-Friday. Each group is over an hour of outdoor time plus transportation time to and from your home. We service Cambridge, Back Bay, South End, and parts of Brookline



$34 half day (morning or afternoon group)

$54 full day (both groups)

Multiple dog households, add $20 per additional dog


When you need to go away, we offer two pet sitting options, upon availability.

In-Home Pet Sitting – we stay at your place with your pup. House sitting tasks such as mail, trash, and plant watering can be provided. Cats, birds, fish, etc can also be cared for.

Home Boarding – your pup comes home with one of us to be loved and cared for as our own.

All overnight services are available for current hiking clients only. Owners going away can be very stressful on our pets. We believe that in order to stay with a pup at their place, or bring a pup comfortably into our home, it is important for us to know your dog well and for their routine to be as normal as possible. Because of this, we will only provide overnight services for current hiking clients.



Both In-Home Pet Sitting and Home Boarding are $75 per 24 hour period and include a daily group hike with the cost of service.


We all love our pups and want our relationship with them to be a happy and strong one. Learning how to communicate through positive training allows you to enjoy your time together to the fullest.

Our staff trainer Amber of Pawsitive Development, along with her pups Tucker and Oakley, offer personal training sessions along with blog posts, product reviews, tutorial videos, nutritional info and more to help you and your dog build your bond closer than ever.

Let’s Give ‘Em Something to Talk About

Kelly and Zach are truly the best!!

They give such quality time to my dog and are always thoughtful and attentive to all the dogs in their care.

He loves going on his hikes, playing with other dogs and gets great exercise!

Leah T

If I tried to document all of the ways in which A Dog’s Life Boston has been a tremendous service to myself and my pet, it would be an epic fail on my part.  Kelly has gone above and beyond what I expected from a dogwalker.  She’s always on time, reliable, and friendly.  My dog greets her with enthusiasm and excitement that he normally reserves for myself and close friends.  He couldn’t be happier and it shows when he gets home and falls asleep after letting out a big, content sigh, as if to say “today was a good day.”

Adam K

Kelly and her carefully selected crew are AMAZING…

We’ve used multiple services since our first dog was a puppy so I’d like to think we know a good dog walker when we see one.

Marissa A

Meet the Team

Kelly and Penzi

Kelly and Penzi

Founder and Head Adventurers



Off-Leash Adventure Leader



Senior Off-Leash Adventure Leader

Amber and Oakley and Tucker

Amber and Oakley and Tucker

Off-Leash Adventure Leader and Trainer Extrodinaire