Physical, mental, and social stimulation for the active dog outside Boston.

About us

Helping dogs live their best lives in:
Dedham - Needham- Westwood- Milton- West Roxbury - Wellesley

Our Values
At Running Free Dog Adventures, we are dedicated to creating an environment where dogs can safely live their healthiest lives through unleashed running, play and exploration in nature.
Our commitment extends beyond the immediate adventure – we actively respect and preserve the natural environments we explore, ensuring they remain pristine for generations to come.

Meet the team

Lindsey
FOUNDER & ADVENTURE GUIDE
Lindsey's roots are grounded on Cape Cod, where her deep love for dogs and the great outdoors blossomed.
When she's not in the woods with Sky and her friends, you'll likely find her enjoying quality time with family and friends.
Lindsey has a passion for travel, exploring new horizons whenever the opportunity arises. In addition to her two human daughters, she proudly calls Sky her 3rd and furrier child. Lindsey is lucky to spend her days in the woods along side her wonderful husband Brian.

Brian
CFO (Chief fun officer) & ADVENTURE GUIDE
Hailing from Ireland, Brian has embraced Boston as his home. He shares a love for exploring new trails with Sky and her companions, infusing each adventure with a sense of fun.
Beyond the trails, Brian is dedicated to coaching his daughters, indulging in golf, and avidly following European soccer matches.
His diverse interests and infectious enthusiasm make him a valuable member of our Running Free Dog Adventures team.

Maureen
ADVENTURE GUIDE
Hi, I’m Maureen! I’m a boy mom, a boy grandmom, and a proud Black Lab mom—and yes, depending on the day, any one of those might be my favorite role.
I love peaceful walks in the woods, breezy beach strolls, and spontaneous ga mes of Fetch. (Yes, I’ll throw the ball a hundred times if it makes them happy!)
What began as a simple favor many years ago has turned into the best job I’ve ever had. I’m lucky enough to spend my days doing what I love, and every day brings a little dirt, a lot of laughter, and so much joy.
At the end of each adventure, there’s nothing better than a good cuddle and knowing we all had the best time out there—dogs and humans alike.

Kyle
ADVENTURE GUIDE
Hello, I'm Kyle! I live in Dorchester with my rescue dog Wyatt, my daily hiking buddy and best pal.
Before joining Running Free, we spent hours exploring Blue Hills on our own, experiencing firsthand how healing nature can be.
Now we have hiking buddies to join us, and it’s been wonderful becoming part of a pack. I have a special place in my heart for rescues and anxious pups, and it’s always rewarding to see how time outdoors helps them relax, play, and grow in confidence.
Dogs have been my closest companions all my life, and caring for them is where I feel most at home.

John
ADVENTURE GUIDE
Hello, I'm John. I love all animals but especially dogs.
Nothing makes me happier than a happy dog!
I spent the best days of my life with my other half Jack hiking thousands of miles over 15 amazing years.
I am so incredibly lucky that I now get to continue spending my days outdoors helping dogs live their best life!

Madison
ADVENTURE GUIDE
Hey, I'm Madison! I graduated from the University of Vermont in 2024 with a degree in Animal Science.
Since then, I have been applying my knowledge in working with dogs. I am a Certified Professional Dog Trainer, Knowledge Assessed, and adhere by LIMA training standards.
I love providing outlets for dogs to fulfill their needs whether by running, sniffing and exploring, or by challenging them with mental stimulation in training.
My journey began with my family dog, Paula, who I trained to hike and run with me off-leash. I saw first hand the benefits this had on her, and I'm so happy to help your dogs benefit from this daily!

Christi
ADVENTURE GUIDE
Hi, I’m Christi! A little dirt, noise, and chaos are pretty much part of my everyday life as a boy mom (x2) and dog mom (of one precocious Bernadoodle named Harvey) — I wouldn’t have it any other way!
As a gardening enthusiast, wandering through the woods and watching the seasons change with a pup pack by my side is the perfect morning. There’s just something about fresh air, muddy paws, and a good trail that makes everything better.

Jocelyn
ADVENTURE GUIDE
Hi, I’m Jocelyn! I’m an Air Force veteran and Dedham Mom who loves pet sitting and dog walking.
My military background has also given me a strong foundation in first aid, safety, and staying calm and confident in all kinds of situations.
I’ve always had a natural connection with dogs, and I think they respond to my calm, easygoing personality. And really, who wouldn’t love spending their days surrounded by happy pups?
I’m so excited to be part of the Running Free team and can’t wait to meet your dogs, get to know their personalities, and enjoy lots of adventures together!

Donna
ADVENTURE GUIDE
Hi there! I’m Donna. One of my favorite ways to spend time is hiking off-leash with my German Shepherd. Being in nature has always grounded me. That love was planted early, during childhood camping trips throughout New England spent exploring the woods, fishing, canoeing and simply appreciating the outdoors. When you can share those experiences with your four-legged pal by your side, they’re even better. Add a whole pack of dogs to the adventure, and the joy multiplies!
After 17 years as a project manager in the medical software industry, I stepped away to focus on raising my three children. With two now in college and one headed that way soon, I didn’t hesitate when the opportunity came along to become an adventure guide for your furry family members. Now I get to share what I love with a pack of happy pups—spreading joy in every direction!

Meet some of the pack

























Memberships & Certifications
Certification
First Aid & CPR

Membership
NAPPS

Certification
Insured & Bonded


The benefits of running free adventures
By combining off-leash play, pack walks, and group adventures, dogs can enjoy a well-rounded experience that addresses their physical, social, and mental needs.
Knowing their dogs are enjoying social interactions and adventures alleviates feelings of guilt associated with a busy schedule. Owners can have peace of mind knowing their dogs are not only physically active but also mentally stimulated and socially fulfilled, contributing to their overall well-being. And....they take LONG naps!
Rest assured your dog is in the care of dog loving, compassionate professionals that love your dog as if they were our own. We give lots of cuddles and kisses. We are also CPR and FIrst-AId certified, Licenced, Insured and Bonded.
Group adventures in varied environments offer dogs new sights, smells, and terrain, stimulating their natural curiosity.
We keep you in the loop on everything. You will receive photos, videos and a GPS map of our adventures.
