The Fells Trail Trek
$25 / 45-min walk
A single small-group hike on the Fells Trail.
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🌲 Adventures at the Middlesex Fells
Tails that never stop wagging.
Small-group trail walks, joyful exercise, and loving in-home care — because your best friend deserves the best day, every day.
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Real Trail Time
Every adventure happens on the beautiful Fells Hiking Trail — fresh air, real terrain, real fun.
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Small, Happy Packs
Walks are capped at three dogs so every pup gets attention, safety, and plenty of sniffing.
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Treated Like Family
Trusted, attentive, and dog-obsessed care from someone who treats your pet like their own.
What We Offer
Pick your perfect adventure
The Pack Pass
$20 / 45-min walk
For the 3+ walks-a-week crowd. Same great trek, better price.
Learn more →Home & Hound Sitting
$60 / day
Overnight, in-home care so your pup never feels alone.
Learn more →Ready to make your dog's day?
Let's get those paws on the trail. Reach out and we'll plan the perfect routine.
Book a WalkPet Services
Adventures & care, tailored to your pup
Every service is built around safety, exercise, and a whole lot of love. All walks take place on the scenic Fells Hiking Trail.
Single Walk
The Fells Trail Trek
$25 · 45 minutes
Lace up the leash — it's adventure time! Your dog joins a small, friendly pack of no more than three pups for a 45-minute ramble through the legendary Fells Hiking Trail. We're talking winding wooded paths, leaf-crunching sniff sessions, squirrel surveillance, and just enough hills to send them home happily tuckered out. Every trek is led at your dog's pace with constant supervision, fresh water, and a post-walk note so you know exactly how the fun went down. It's the kind of outing that turns a ho-hum afternoon into the best part of your dog's day.
- ✔ 45 minutes of guided trail time
- ✔ Small group — max 3 dogs total
- ✔ Scenic Fells Hiking Trail
- ✔ Fresh water & a happy-tails update
★ Best Value
Membership
The Pack Pass
$20 · per 45-min walk
For the pups who live for the trail! The Pack Pass is our membership made for go-go-go dogs who get out three or more times a week. You get the same beloved 45-minute, small-group Fells adventure (max three dogs) at a wagging-good member rate of just $20 per walk. Beyond the savings, your dog gets the magic of routine — familiar trails, familiar pals, and the joyful confidence that comes from knowing today is a walk day. Healthier body, happier heart, and a calmer, better-behaved buddy at home. Consider it your dog's standing reservation with the great outdoors.
- ✔ Member rate: $20 per 45-min walk (save $5 each!)
- ✔ Designed for 3+ walks every week
- ✔ Same 45-min small-group Fells trek
- ✔ A consistent, healthy routine your dog will love
In-Home Care
Home & Hound Pet Sitting
$60 · per day
Going away? Your pup gets a staycation! With Home & Hound, your dedicated pet sitter moves right into your home so your dog keeps every comfort they know and loves — same cozy bed, same favorite window, same familiar smells. We handle it all: hearty meals right on schedule, refreshing walks, belly rubs on demand, playtime, and all the cuddles and undivided attention a good dog deserves. No lonely kennels, no stressful drop-offs — just a happy companion keeping your best friend company day and night. You travel with peace of mind; your dog barely notices you left.
- ✔ Overnight, in-home stays
- ✔ Feeding, walking & potty breaks
- ✔ Cuddles, play & constant companionship
- ✔ Your home looked after, too
Not sure which fits best?
Tell us about your pup and we'll help you build the perfect plan.
Ask Us AnythingAbout
Our Story
The person behind the paws — and the promise to care for your dog like my own.
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Meet Helen 🐾
Hi, I'm Helen Zhou — a proud Winchester High School alumna and the heart behind Helen's Happy Paws. I've called the Winchester area home for many years, and over that time I've completely fallen in love with the Middlesex Fells. It started simply: long walks there with my own dogs, season after season, learning every winding path, shady grove, and good sniff spot. What began as my favorite part of the day quickly became something I wanted to share with other dogs and the people who love them.
Dogs aren't just my business — they're my whole world. I share my home with two dogs and a cat, so a happy, busy household full of paws is just my normal. With 3+ years of dog-walking experience, I've learned to read canine body language, keep group walks calm and safe, and tailor every outing to the pup in front of me — whether that's a bouncy young adventurer or a gentle senior who likes to take it slow. Watching a nervous dog blossom into a confident, tail-wagging trail buddy never gets old.
Above all, I know that handing over your best friend (and often a key to your home) takes real trust. I don't take that lightly. I'm reliable, communicative, and detail- oriented — I show up when I say I will, follow your routines to the letter, and send updates so you always know your pup is safe and happy. Every dog in my care is treated exactly like one of my own: with patience, attention, and a whole lot of love. Your dog's wagging tail is my favorite report card.
Contact Us
Let's Talk Tails
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- 📞Phone
- ✉️
- 📍Service Area
Winchester & Woburn, MA
- 🕒Hours
11 AM – 5 PM
Gallery
Wagging in the wild
A few of our favorite faces on (and off) the trail.
Jobs
Join the Pack
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