Small-group dog hiking and dog walking with door-to-door pickup. Real trail exercise for dogs in Greenwich, Stamford, Darien, Westport, and the surrounding area.
Text to Book — (917) 583-9279Dog hiking in Greenwich, CT and nearby towns for owners who want more than a short neighborhood walk.
Dogs that need real trail exercise, new smells, and mental stimulation instead of the same block every day.
Door-to-door pickup so you can stay focused on work or family while your dog gets a proper outing in local wooded areas.
Safe socialization on trails near Greenwich, Stamford, and surrounding towns — without the chaos of large packs.
We start with a short meet-and-greet so we can learn your dog’s personality, energy level, and any special needs before the first hike.
We pick your dog up at home and take them on a small-group trail adventure (usually 3–4 dogs max) for real exercise, sniffing, and safe socialization.
You get photos and a quick update. Your dog comes home tired, happy, and ready to rest.
Small-group trail hikes with door-to-door pickup. Competitive rates for real exercise in Greenwich and the surrounding area.
$60
One small-group trail hike (60–90 min). Includes pickup, drop-off, and a photo update. Perfect way to try Tail Trails.
$55 / hike
2 or more hikes per week. Priority scheduling, consistent routine, and the best per-hike rate. Most popular option.
$95 / hike
Same small-group trail hike for two dogs from the same household. Weekly rate: $85 per hike when booked 2+ times per week.
All hikes include door-to-door pickup and drop-off in Greenwich and surrounding areas. Limited spots per hike.
Supervised outdoor dog hiking focused on exercise and safe socialization. Ideal for dogs in Greenwich and nearby towns who need more than a neighborhood walk.
We handle pickup and drop-off so you don’t have to rearrange your day. Consistent scheduling available for busy owners in Fairfield County and nearby New York areas.
Recurring weekly dog hikes keep your dog in a healthy routine and give you predictable pricing and priority booking.
Tail Trails provides dog hiking and dog walking with door-to-door service in Greenwich, CT and surrounding communities within roughly a one-hour drive, including:
Greenwich, Stamford, Darien, New Canaan, Westport, Norwalk, Wilton, Ridgefield, and nearby Fairfield County towns.
Port Chester, Rye, Scarsdale, White Plains, Mamaroneck, and other nearby Westchester towns within about an hour of Greenwich.
Yes. Tail Trails specializes in small-group dog hiking and dog walking with door-to-door pickup in Greenwich, Connecticut and the surrounding area.
We serve Greenwich and nearby towns within about a one-hour drive, including Stamford, Darien, New Canaan, Westport, Norwalk, Wilton, Ridgefield in Connecticut, plus Port Chester, Rye, Scarsdale, and White Plains in New York.
We keep groups small, typically 3–4 dogs maximum, so every dog gets attention and the experience stays safe and enjoyable.
Yes. Door-to-door pickup and drop-off is included so you don’t have to drive to a trailhead or rearrange your schedule.
For many dogs, yes. Trail hikes provide more physical exercise, mental stimulation from new smells and terrain, and better socialization than a standard neighborhood walk.
A trial small-group trail hike is $60. Weekly memberships are $55 per hike when booked two or more times per week. Two dogs from the same household start at $95 per hike. All prices include door-to-door pickup and drop-off.
Yes. We offer door-to-door dog hiking and walking in Greenwich and surrounding areas within about an hour drive, including Stamford, Darien, New Canaan, Westport, Norwalk, Wilton, Ridgefield, and nearby New York towns such as Port Chester, Rye, and Scarsdale.
We use local wooded trails and natural areas in and around Greenwich, Stamford, and nearby towns — places that give dogs real outdoor time away from sidewalks and traffic.
Fastest way to get started. Text us your dog’s name, town, and preferred days. We’ll confirm availability and send a simple payment link.
Or email: tailtrailsct@gmail.com
Greenwich, CT · Dog Hiking & Walking · Door-to-Door Service
