55This was a nice patch of woods to wander around in. There is a wide central path with an offshoot to the river bank. The underbrush is also sparse at the moment for much of it so hiking off path isn't too hard if desired. Even with only a few days since the last rain we didn't have any issues with mucky ground. There's a nice view of the river, but it didn't look good for swimming. Woodland and water birds are in the area if you're interested in that. If you bring your own camping chair, there would be nice places to sit for a bit watching the scenery. As stated, it is unfenced, so that needs to be taken into account. The host also warned me about ticks, which is to be expected in any woods or long grass as the weather warms, so precautions should be taken accordingly. Horses were visible on the farm on the way into the spot, but no dogs, people, or domestic animals were visible or audible from the woods. Overall a great experience!Angela S.
Angela S.
April 2021
This was a nice patch of woods to wander around in. There is a wide central path with an offshoot to the river bank. The underbrush is also sparse at the moment for much of it so hiking off path isn't too hard if desired. Even with only a few days since the last rain we didn't have any issues with mucky ground. There's a nice view of the river, but it didn't look good for swimming. Woodland and water birds are in the area if you're interested in that. If you bring your own camping chair, there would be nice places to sit for a bit watching the scenery. As stated, it is unfenced, so that needs to be taken into account. The host also warned me about ticks, which is to be expected in any woods or long grass as the weather warms, so precautions should be taken accordingly. Horses were visible on the farm on the way into the spot, but no dogs, people, or domestic animals were visible or audible from the woods. Overall a great experience!
55Our girls had so much fun! The paths were big enough to play and sniff, and was pretty easy to navigate off the trail as well if you don’t mind a few thorns. Holly G.
Holly G.
January 2023
Our girls had so much fun! The paths were big enough to play and sniff, and was pretty easy to navigate off the trail as well if you don’t mind a few thorns.
55Really nice! A fully grassy yard with sun and shade if you wanted it. The dogs had a blast running and rolling around. It was a bit muddy, but with snow still on the ground that’s pretty expected. There were active dogs playing and occasionally barking in some of the visible surrounding yards that made it a little rough in the beginning with our one reactive pup, but hey, everything’s a training opportunity! In the future we may avoid holidays/weekends here when others are likely to be out with their dogs, but we’ll definitely return! Finding the location and parking was easy.Mindy & Ryan C.
Mindy & Ryan C.
December 2020
Really nice! A fully grassy yard with sun and shade if you wanted it. The dogs had a blast running and rolling around. It was a bit muddy, but with snow still on the ground that’s pretty expected. There were active dogs playing and occasionally barking in some of the visible surrounding yards that made it a little rough in the beginning with our one reactive pup, but hey, everything’s a training opportunity! In the future we may avoid holidays/weekends here when others are likely to be out with their dogs, but we’ll definitely return! Finding the location and parking was easy.
Fully Fenced Yard Near Double Rock Park! | Sniffspot
55Another great visit! Last minute booking but the yard was clean. Dogs LOVE having the thick grass to roll around in (and occasionally gnaw on).Mindy & Ryan C.
Mindy & Ryan C.
December 2020
Another great visit! Last minute booking but the yard was clean. Dogs LOVE having the thick grass to roll around in (and occasionally gnaw on).
Fully Fenced Yard Near Double Rock Park! | Sniffspot
55It’s a bit bushy and the dogs next door bark like crazy, but other then that my dog had a fun time running around and we even brought our ferret for some outside time!Elainea C.
Elainea C.
May 2022
It’s a bit bushy and the dogs next door bark like crazy, but other then that my dog had a fun time running around and we even brought our ferret for some outside time!
55I’ve been in large fenced in yards and my dog has gotten plenty of exercise, but there is NOTHING that compares to wide open fields to truly allow them to stretch their legs at full out sprints.
I’ve been to Sarah’s property countless times. It’s remote, beautiful and completely ours with no distractions for the hour my dog and I are there. I’ve said it here before….it’s simply good for a dog’s soul. When we take a few minutes break and sit in the tall grass together in between running he showers me with kisses. He’s ecstatic. That’s kinda all you need to know. Russell S.
Russell S.
December 2021
I’ve been in large fenced in yards and my dog has gotten plenty of exercise, but there is NOTHING that compares to wide open fields to truly allow them to stretch their legs at full out sprints.
I’ve been to Sarah’s property countless times. It’s remote, beautiful and completely ours with no distractions for the hour my dog and I are there. I’ve said it here before….it’s simply good for a dog’s soul. When we take a few minutes break and sit in the tall grass together in between running he showers me with kisses. He’s ecstatic. That’s kinda all you need to know.
55My dog and I live in an apartment complex, which is why I try and visit Sarah’s property weekly. A buddy of mine (former neighbor) has a female dog, same age as mine, and they were inseparable playing on the tennis courts in my complex until they moved away last year. My boy was heartbroken.
We get together once every few months at the farm. I can’t articulate just how good for their psyches it is to reunite. They run WILD on such a huge expanse of open fields. Non-stop, full out sprinting. You just can’t replicate it. Sarah’s property has been a godsend for us going in 2 years. Russell S.
Russell S.
December 2021
My dog and I live in an apartment complex, which is why I try and visit Sarah’s property weekly. A buddy of mine (former neighbor) has a female dog, same age as mine, and they were inseparable playing on the tennis courts in my complex until they moved away last year. My boy was heartbroken.
We get together once every few months at the farm. I can’t articulate just how good for their psyches it is to reunite. They run WILD on such a huge expanse of open fields. Non-stop, full out sprinting. You just can’t replicate it. Sarah’s property has been a godsend for us going in 2 years.
55Beautiful property with amazing fields for my dogs to run with their friends. So much open space and a nice treeline and partial fence buffer from the adjoining properties.Sarah S.
Sarah S.
January 2022
Beautiful property with amazing fields for my dogs to run with their friends. So much open space and a nice treeline and partial fence buffer from the adjoining properties.
55It was a cold, windy day and our pups didn’t care. They loved running around the field and going up towards the pond. We look forward to coming back sometime in the spring/summer!Austin D.
Austin D.
February 2022
It was a cold, windy day and our pups didn’t care. They loved running around the field and going up towards the pond. We look forward to coming back sometime in the spring/summer!
55Another fabulous time - just a heads up, there are lots of stickers in the field between the pond and the top of the driveway, so might want to avoid that section for now unless you want to pull them out of puppy paws! Bethany P.
Bethany P.
March 2022
Another fabulous time - just a heads up, there are lots of stickers in the field between the pond and the top of the driveway, so might want to avoid that section for now unless you want to pull them out of puppy paws!
55We had a fabulous time exploring at Dragonfly Hollow!!! Sarah made sure we knew how to get to the property and greeted us when we arrived. It was great to let the dogs roam around off leash and just be dogs. The property was clean, safe, and had different terrain for lots of fun.Brandy I.
Brandy I.
October 2021
We had a fabulous time exploring at Dragonfly Hollow!!! Sarah made sure we knew how to get to the property and greeted us when we arrived. It was great to let the dogs roam around off leash and just be dogs. The property was clean, safe, and had different terrain for lots of fun.
How do Chestertown's private dog parks work?
Private rentals by the hour
Our hosts are locals that are renting their yards and private land to dog owners
Trust and safety first
Spots are designed for safety and both hosts and guests are reviewed after each visit
Designed for private play
Only the people and dogs in your booking are allowed in the spot during your visit
Reactive dogs welcome
Many of the spots we list are designed with sensitive dogs in mind
Become a Sniffpass holder!
Get discounts on all bookings at all spots by buying monthly credits! Learn more!
FAQ about our Chestertown dog parks
Are dog parks good for dogs?
It is important for dogs to have off leash exercise to sniff and run. But the free and open nature of public dog parks has drawbacks. There could be aggressive dogs, disease transmission and cleanliness issues. For this reason, many dog behaviorists discourage visiting public dog parks and recommend Sniffspot's private dog parks. Sniffspot private dog parks only allow one guest to book at a time and are not open to the public, which solves many of these issues.
Are dog parks safe?
While public dog parks have a number of safety issues, such as aggressive dogs, disease transmission and general cleanliness, Sniffspot dog parks much safer than public dog parks. With Sniffspot all bookings are private for just you and dogs you bring with you and we require all dogs to be vaccinated (or have equivalent titers). All Sniffspot locations are vetted and reviewed by guests so you can find the perfect place for you and your dog. 98% of reviews on Sniffspot visits in the Chestertown area are 5 stars.
How do I know if a dog park works for my dog?
You can filter Sniffspot dog parks by fencing and distractions. If your dog doesn't have good recall, you can visit one of our 301 fully fenced dog parks in the area. If your dog is reactive to other dogs, you can visit one of our 30 off leash areas where there are no dogs audible or visible nearby. You can also filter locations to avoid other domestic animals and people. We also recommend reading reviews and reaching out to the host with any questions.
What is the best dog beach near Chestertown?
The best Sniffspot dog beach near Chestertown is Ft Smallwood Dog Adventure Park. At Sniffspot beaches dogs can generally be off leash.
Does Chestertown have any fully fenced dog parks?
Sniffspot has 301 fully fenced dog parks in or near Chestertown. Browse all fully enclosed options.
Where are good dog hiking trails near Chestertown?
The Chestertown area has 301 Sniffspot locations with private trails for you and your dog to walk or hike. Dogs can generally be off leash on Sniffspot trails. The most popular trail is Ft Smallwood Dog Adventure Park.
Are there dog agility courses for rent in Chestertown?
Sniffspot has dog parks with agility equipment and/or dog obstacles in or near Chestertown. The most popular agility option is Ft Smallwood Dog Adventure Park.
Where in Chestertown can I find a pool for dog swimming?
Can I rent a field for my dog to run near Chestertown?
There are 301 Sniffspot dog parks that offer fields in or near Chestertown where dogs can be off leash. The most popular field is Ft Smallwood Dog Adventure Park.