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.
55Perfection! Stunning property with so much room for our two energetic dogs to run and play. Thank you for making this available. We will be back! Melissa J.
Melissa J.
August 2021
Perfection! Stunning property with so much room for our two energetic dogs to run and play. Thank you for making this available. We will be back!
55Perfect place to decompress! Really beautiful and peaceful. Entrance and parking directions were clear and my pup had a great time! Amazing escape from the city for both him and I. Emily M.
Emily M.
August 2021
Perfect place to decompress! Really beautiful and peaceful. Entrance and parking directions were clear and my pup had a great time! Amazing escape from the city for both him and I.
55Awesome! It was our first time using Sniff Spot so we weren't sure what to expect, but everything was straightforward and Sarah was very nice. We definitely plan on coming back!Annie G.
Annie G.
April 2021
Awesome! It was our first time using Sniff Spot so we weren't sure what to expect, but everything was straightforward and Sarah was very nice. We definitely plan on coming back!
55great place for running dogs off leash! take a walk through the woods behind the house, it leads to the river! Our fur babes lived the pond as well perfect for fetching sticks! we will be back!!Dawn B.
Dawn B.
May 2021
great place for running dogs off leash! take a walk through the woods behind the house, it leads to the river! Our fur babes lived the pond as well perfect for fetching sticks! we will be back!!
55Lovely morning at Dragonfly Hollow! Lucie gets so excited as soon as we turn down the drive, she thoroughly enjoyed her first swim of the year! Michele M.
Michele M.
May 2021
Lovely morning at Dragonfly Hollow! Lucie gets so excited as soon as we turn down the drive, she thoroughly enjoyed her first swim of the year!
55Such a beautiful spot - the pond, the fields, everything. It was quiet and secluded with tons of space to explore. The host was very kind when we met her. We will absolutely be back soon! Dustin H.
Dustin H.
May 2021
Such a beautiful spot - the pond, the fields, everything. It was quiet and secluded with tons of space to explore. The host was very kind when we met her. We will absolutely be back soon!
55We were unable to attend due to an unforeseen circumstance however, the host was lovely and offered to let us come at a different time at no extra cost. We were unable to attend due to work schedules but this gesture will certainly have us returning in the future!Sonja S.
Sonja S.
May 2021
We were unable to attend due to an unforeseen circumstance however, the host was lovely and offered to let us come at a different time at no extra cost. We were unable to attend due to work schedules but this gesture will certainly have us returning in the future!
55We had the best time here! So much room to run and explore, it was wonderful. We had 11 dogs with us and it was truly a dream come true for them. There’s nothing better than seeing your dogs loose and running free. I would definitely recommend this spot and can’t wait to come back again!
The only thing I would say to be aware of is that there’s a lot of wildlife poo around that is apparently delicious 🤮 Amanda F.
Amanda F.
January 2021
We had the best time here! So much room to run and explore, it was wonderful. We had 11 dogs with us and it was truly a dream come true for them. There’s nothing better than seeing your dogs loose and running free. I would definitely recommend this spot and can’t wait to come back again!
The only thing I would say to be aware of is that there’s a lot of wildlife poo around that is apparently delicious 🤮
55Another fantastic doggy day and this time with a friend. Both dogs had so much fun running all over this large property! This was Lily’s 2nd time and Gippers 1st time. It was great to meet Sarah. What a very nice host. Can’t wait to get there in warmer weather. Lily is going to love the pond! Lisa F.
Lisa F.
January 2021
Another fantastic doggy day and this time with a friend. Both dogs had so much fun running all over this large property! This was Lily’s 2nd time and Gippers 1st time. It was great to meet Sarah. What a very nice host. Can’t wait to get there in warmer weather. Lily is going to love the pond!
55This was such an amazing property to let our dog off leash and Sarah was an equally amazing host. She gave us a great lay of the land and we were able to explore the woods, creek, pond, and acres on acres of freedom for our pup!Jenna C.
Jenna C.
January 2021
This was such an amazing property to let our dog off leash and Sarah was an equally amazing host. She gave us a great lay of the land and we were able to explore the woods, creek, pond, and acres on acres of freedom for our pup!
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. 97% 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 167 fully fenced dog parks in the area. If your dog is reactive to other dogs, you can visit one of our 32 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.
Does Chestertown have any fully fenced dog parks?
Sniffspot has 167 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 7 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 Over 10 Acres Fully Fenced Farm.
Are there dog agility courses for rent in Chestertown?
Can I rent a field for my dog to run near Chestertown?
There are 48 Sniffspot dog parks that offer fields in or near Chestertown where dogs can be off leash. The most popular field is Michele's Private Dog Park In Dover.