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.
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.
55Just a wonderful place. Acres and acres of free land. Like a sanctuary. Allows your dog to be a dog and experience the bliss of open spaces to run and play, or just roll in the grass and experience freedom like only nature provides. I mean you can see it in their eyes and movements. Good for their bodies and soul. Solid and safe opportunity for off leash training. Russell S.
Russell S.
March 2021
Just a wonderful place. Acres and acres of free land. Like a sanctuary. Allows your dog to be a dog and experience the bliss of open spaces to run and play, or just roll in the grass and experience freedom like only nature provides. I mean you can see it in their eyes and movements. Good for their bodies and soul. Solid and safe opportunity for off leash training.
55Very lovely, secluded piece of land. Far enough off the main road, the driveway is gravel but nothing my little hatchback couldn’t handle. Loved spending time at the pond. Quiet and relaxing. Perfect spot for off-leash runs. Can’t wait to return.Ashley B.
Ashley B.
July 2021
Very lovely, secluded piece of land. Far enough off the main road, the driveway is gravel but nothing my little hatchback couldn’t handle. Loved spending time at the pond. Quiet and relaxing. Perfect spot for off-leash runs. Can’t wait to return.
55This continues to be our weekend respite between long work weeks. A place where he regains a little piece of his soul and recharges his batteries. Thanks again Sarah for making your farm available :)Russell S.
Russell S.
August 2021
This continues to be our weekend respite between long work weeks. A place where he regains a little piece of his soul and recharges his batteries. Thanks again Sarah for making your farm available :)
55Could not have been better! The perfect place for dogs to run, swim and have fun. Sarah was a wonderful host, made sure we had everything we could need. Can't wait to go back!Hannah K.
Hannah K.
August 2021
Could not have been better! The perfect place for dogs to run, swim and have fun. Sarah was a wonderful host, made sure we had everything we could need. Can't wait to go back!
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!
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 185 fully fenced dog parks in the area. If your dog is reactive to other dogs, you can visit one of our 31 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 185 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 6 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 The 80 acre wood.
Are there dog agility courses for rent in Chestertown?