Annapolis Dog Walkers and Pet Sitters

Tails on Trails is the premier dog walking service for the city of Annapolis in Anne Arundel County. Situated on the Chesapeake Bay, Annapolis is an animal lovers dream with beautiful dog-friendly parks. The walking trails at Back Creek Nature Park and Quiet Waters are a dog lovers dream!

Our Annapolis dog walkers and pet sitters will visit your home to take care of your dog or cat whether they need at bathroom break, walk, litter box change, or some play-time while you’re away.

We also take care of pets in Crownsville, Davidsonville and Parole. Our staff has experience working with pets just like yours and will make sure your family’s best friend always feels great.


Annapolis Dog Walkers and Dog Walking


Why Choose Tails on Trails for Your Dog Walking Annapolis, MD

  • GPS – All walks are monitored and time tracked
  • Background checks – Yearly – By an independent, professional company
  • Employees not Contractors
  • Insured
  • Bonded
  • Time verification – Computerized monitoring Check-in App
  • Training – Animal behavioral – Yearly – Board certified Veterinarian
  • Training – Harness, leash, collar
  • Training – Security – Yearly – By an independent, accredited company
  • Our Guarantee


Interested in learning more about our services or setting an appointment?

Visit our Pet Care Services page, email us, or give us a call at (855) 925-5597.


Places to walk your dog in Annapolis, MD.

Dog Walking Locations Annapolis

Tails on Trails has a Pinterest Page dedicated to great dog walking in Annapolis. Check us out!


Annapolis is a great place to walk your pet. Whether you’re looking for a park, a pet friendly restaurant, or a nice tree lined neighborhood walk, Annapolis has it all. Check out some of our blog links for great insider tips on owning a dog in the Annapolis area? Perfect places to walk your dog, ideas about where to bring your pet, safety tips and more.


Adjusting to the End of Summer

Tips for your pet’s adjustment to the end of the summer!

Pet Friendly Cruises in Annapolis!

Spend a day on the water checking out the best that the area has to offer. If you haven’t yet taken a cruise through Watermark, it’s a great experience!

 A Fun Outing in Annapolis: Rams Head Tavern

A great brunch choice for your weekend!

A Day Trip to Edgewater: Historic London Town and Gardens

A lovely museum, the grounds including the garden and historic structures make for a great day trip and even better pictures! (seeing is believing!)

Looking for a Break from the Heat

We’re so close to the water, finding the right place to visit is at your fingertips!

The B & A Trail is a great place for a hike.

If you’re looking for a new hiking spot, this is your next perfect find!


Pet Sitting and Dog Walking in Annapolis, Maryland

Tails on Trails is proud to offer premier services to people who love their animals. Although there are many companies to choose from, our dedication to each client is what sets us apart.  It drives us to provide professional training for all of our staff well above the average company.  Our years of experience and proven processes will give you peace of mind and a happy pet.  Our processes include GPS tracking using computerized time tracking software so you know that the walker is there as scheduled, for the time requested.  Our training is ongoing with a licensed veterinarian and behavioral training specialist.  All walkers and staff go through safety and security training yearly with an independent security company.  Our employees are bonded and insured with a liability carrier as well as covered under Workers Compensation Insurance.  All of our processes are designed around providing you excellence in pet sitting and dog walking in Annapolis, Maryland.