Hike More, Worry Less
Dog Hikes in Westchester, Putnam, Dutchess & Fairfield Counties
Give your pup the best part of their day — a 60-90 minute outdoor adventure filled with fun, exercise, and safe social time on scenic trails across the Hudson Valley and lower Connecticut. We handle pick-up, drop-off, and send daily photo updates so you never miss the smiles.
Daily Photo Updates
Door to Door Service
Trusted by Pups + Pup Owners
Choose the Right Hike for Your Dog
Pack hikes
Small, carefully matched groups of friendly dogs hit the trail together for a structured social adventure. Proper socialization leads to happier, more balanced dogs — and there's nothing better for your pup than burning energy alongside new four-legged friends. Ideal for confident, social dogs who love company.
Private hikes
Solo trail time for dogs who do best with focused, individual attention. Whether your pup is reactive, recovering from surgery, an anxious senior, or just prefers their own pace, private hikes give them the exercise and mental stimulation they need without the stress of a group. Perfect for dogs who need a calmer, customized experience.
What's Included In Every Hike
Every Tailblazers hike comes with the same level of care — no matter which option you choose.
60-90 Minutes of Trail Time
Real, sustained outdoor exercise on beautiful trails throughout the region.
Daily Photo & Video Updates
Watch your dog's adventure unfold with real-time updates straight to your phone.
Trained, Insured Handlers
Our team is fully insured, dog-safety certified, and trained in canine first aid.
Door-to-Door Pick-Up & Drop-Off
We come to you. Your pup is picked up, hiked, and returned home tired and happy.
Small, Carefully Matched Groups
Pack hikes are kept intentionally small, with dogs matched by energy, size, and temperament.
Trail Variety
We rotate through scenic trails so your dog gets new sights, smells, and experiences regularly.
Where We Hike
Tailblazers serves dogs across Westchester, Putnam, Dutchess, and Fairfield counties — covering some of the most beautiful hiking terrain in the Hudson Valley and southwestern Connecticut.
WESTCHESTER COUNTY
TOWNS WE SERVE:
- Bedford - Chappaqua - Katonah - Pound Ridge - Mount Kisco - Armonk - North Salem - Somers & surrounding towns.
FAVORITE TRAILS:
Ward Pound Ridge Reservation - Rockefeller State Park Preserve - Teatown Lake Reservation.
TOWNS WE SERVE:
Brewster - Carmel - Mahopac - Cold Spring - Patterson - Kent & surrounding areas.
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FAVORITE TRAILS:
Fahnestock State Park - Hudson Highlands State Park.
PUTNAM COUNTY
FAIRFEILD COUNTY
TOWNS WE SERVE:
Greenwich - New Canaan - Darien - Wilton - Ridgefield - Westport - Danbury & surrounding Connecticut towns.
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FAVORITE TRAILS:
Devil's Den Preserve and Sherwood Island State Park.
TOWNS WE SERVE:
Pawling - Patterson - Beacon - Fishkill & the southern Dutchess region.
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FAVORITE TRAILS:
Stony Kill Farm and Hudson Highlands.
DUTCHESS COUNTY
How It Works
BOOK YOUR HIKE
Reach out to schedule. We'll learn about your dog and find the right fit (private or pack).
PICKUP TIME
On hike day, we arrive at your door with a clean, climate-controlled vehicle.
TRAIL TIME BEGINS
Your dog gets 60-90 minutes of structured outdoor adventure with our team.
HAPPY PUP RETURNS
We drop them off worn out, fulfilled, and ready for a long nap. You get photos throughout.
More Than Just a Walk
Real exercise. Real stimulation. Real results — for your dog and for you.
PHYSICAL EXERCISE
Critical for dogs of all ages. Regular hiking helps prevent obesity, supports heart and joint health, and burns the energy that often turns into destructive behavior at home.
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MENTAL STIMULATION
New trails mean new smells, new sights, and new sounds — all of which engage your dog's brain in ways a backyard or neighborhood walk simply can't.
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SOCIALIZATION
Helps dogs become more confident, calm, and well-adjusted around other dogs and humans.
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A TIRED DOG IS A HAPPY DOG
After a Tailblazers hike, expect deeper sleep, less anxiety, better behavior, and a generally more relaxed companion at home.
Need Overnight Care? We Offer Boarding Too.
Heading out of town? Tailblazers also offers in-home dog boarding across Westchester, Putnam, Dutchess, and Fairfield counties. Your dog stays in a real home environment with the same trusted team that takes them on hikes — no kennels, no cages, just comfort and care.