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Fear free pet sitting & enrichment adventures

for pups from Watertown to Woodbridge, CT

Hey, I'm Keleigh, founder of Tails & Trails!

From overnight and daytime pet sitting in the comfort of your home to enrichment adventures like movement puzzles, hiking, biking, kayaking, and swimming, my team and I are here to support you and your furry friends with the fear free, positive reinforcement care your pets deserve!

We believe all dogs are good dogs when treated with empathy, compassion, and patience, and have experience working with pups of all types including:

✓ Puppies in training
✓ High energy breeds
✓ Reactive and anxious pets
✓ Pets with medical needs
✓ Senior pets

Whether you’re heading off on your own adventure and want to make sure your fur babies are safe and sound, or your pups are ready to go off on their enrichment adventure, we’re here to help!

Book a free meet & greet!

More than just clients,

Your pets are part of the family.

Your pet’s safety and wellbeing is our #1 priority when they are in our care. That’s why we are Fear Free certified, bonded and insured, pet CPR certified, R+ advocates, and proud members of both the National Association of Professional Pet Sitters and the Pet professional’s Guild.

All paws on deck!

Here's how we can help

Walks & Visits

When you book a visit with us, you’re not just scheduling a standard check-in. Instead, our experienced team takes the time to understand your pet’s preferences, health requirements, and activity levels and then we cater our visit to their unique needs! Whether your pet needs a walk, run, enrichment, playtime, medication, fresh litter, or anything in between, we’ve got you covered.
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Enrichment & Adventures

From agility fitness sessions to an afternoon on the beach, private dog park excursions to scenic hikes and camping trips, we offer a variety of enriching experiences for your furry companion. Our unforgettable outings are designed to stimulate their senses, provide an outlet for their extra energy, and help your pups build confidence around new noises, surfaces, locations, and experiences!
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Overnight & Daytime Pet Sitting

When you're going out of town but your pups can't come along for the ride, I'll be their companion! Your furry family member gets to stay in their familiar surroundings right at home, maintaining their routine while receiving personalized care and attention.
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Woofs & purrs

Notes from happy clients

Lauren Daniel
Lauren Daniel
Finn, Ino, and Maki, German Shepherd
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Being an owner of 3 working-line German Shepherds can make life challenging when it comes to travel and finding pet care coverage. Trying to find someone with the confidence and understanding of the breed that you also simultaneously trust in your home is hard. Keleigh is absolutely amazing! Not only is she one of the most loving and kind people I know, but she is so good at what she does. I highly recommend Keleigh and her Tails & Trails business. She is fantastic with my pups and I know they are in safe, excellent hands with her.
Mindy Nguyen
Mindy Nguyen
Artemis, Australian Cattle Dog and Kiva, Golden Retriever
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Keleigh is amazing! She watched our two dogs, a senior pup who is 12 year old and a puppy who is 6 months old. She was fantastic with them, and they loved her. She’s very thorough about knowing each dog’s needs and really getting to know their quirks. She’s easily reachable throughout the day and offers plenty of adorable pictures. Highly recommend!
Brendan Murray
Brendan Murray
Brooks, Labrador Retriever
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Working with Keleigh has been a great experience. She always communicates exactly what her plan is when she takes my dog for a walk and never fails to send a great picture of their adventures, not to mention how flexible she is. In numerous occasions I would reach out with less than 24 hours’ notice to which Keleigh was more than happy to help out. I’m so happy we were able to get connected and would recommend her to all!
Stephanie England
Stephanie England
Kali and Pixie, Yorkshire Terrier
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Keleigh has been a godsend for us. We have a special senior pup who is wary of strangers, but Keleigh worked her magic and our little old lady did wonderfully with her. Keleigh has assisted with caring for our pets when we've been in a last-minute bind. Her reliability, dependability, and professionalism are unparalleled! We're thrilled to have found her and I wholeheartedly recommend Tails and Trails!
Katie Javaruski
Katie Javaruski
Penny, Redbone Coonhound/Rhodesian Ridgeback Mix
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Keleigh started as just a sitter and has become one of my absolute favorite people!!!Keleigh continues to go above and beyond for my and my sweet Penny! I would trust her with anything!! Keleigh has helped me in a pinch by taking Penny to the vet and face timing me there. She takes care of Penny the same way I would! Penny loves spending time with her. They go on so many fun adventures!!!
Jake Giampa
Jake Giampa
Ari, Staffordshire Bull Terrier
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Keleigh is amazing! She just did an over night at my apartment on New Years Eve for my 3 year American Staffordshire Terrier. During her stay, she did an awesome job staying in touch and keeping me updated on how my pup is doing and the activities they were up to. As well as providing adorable pictures of her. I would 100% recommend using Keleigh for any overnight as well as dog walking
Natalie Taylor
Natalie Taylor
Coda and Mavericc, Labrador Retriever
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Keleigh’s focus on our boys was second to none! Our pups love her and she actually tired out our very active labs for the first time ever! They loved their time with her and look forward to hanging out with her again!
lacey McCabe
lacey McCabe
Cali and Maisie, Labrador Mix
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Keleigh is absolutely amazing with our two dogs. She has stayed with them multiple times while we are out of town and it gave me so much peace of mind to know they were left in her caring and capable hands. Before we found Keleigh, I had so much stress leaving because one of our dogs is very sensitive and would be so anxious when we would have to board her. Now, I have absolutely no issues being away from home- the dogs are safe in their own environment and are so well cared for that I don’t even think they notice I’m gone!
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Ready, set, woof!

What to expect

  • Step 1: First, complete out a simple form to tell us more about your pets and support needs! We’ll reach out within 48 hours via text to confirm basic details, schedule a phone call if necessary, and confirm if we are available to help.
  • Step 2: Next we’ll schedule a time to visit your home where we can talk in more details, meet your fur babies, and you can show us their routines and anything we should know when caring for your pet(s).
  • Step 3: During this process, we’ll also email you a link to activate your account in our online system called “Time to Pet.” This is where we post updates, schedule services, and save all of your pet’s care information.
  • Step 4: Once we’ve met as well as reviewed your pets routines and preferences your services will be officially booked! You’ll pay refundable 25% deposit to secure your dates as a first time client and once we’ve completed your first service, no deposit is required moving forward.
Book a free meet & greet!

Keleigh is the best dog sitter we have used. She understands our anxious dog and makes a concerted effort to ensure she feels comfortable and safe. Keleigh goes above and beyond and I can’t recommend her highly enough!!

Laura B.

Snuggling pups in:

  • Watertown, CT
  • Middlebury, CT
  • Oxford, CT
  • Prospect, CT
  • Bethany, CT
  • Woodbridge, CT

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