Top public and private dog hiking trails in Ossining, New York

🐾The Wildwood Retreat🌳Private 5 Acre Adventure⛰️Fenced in Yard with Splash Zone💦, Trails🥾, Parkour Play🪨, & River Hikes🏞️

Welcome to The Wildwood Retreat! Perched on a spacious mountain property, our spot offers the ultimate private escape for you and your pups. Enjoy a fully fenced backyard featuring a stunning gazebo with 2 comfortable leather couches/futons, optional netted or solid enclosures, a wrought iron chandelier, a portable sturdy Bluetooth speaker, a stocked fridge, and an attached secure dog run. Beyond the yard, explore 5 acres of open land, private trails leading toward a beautiful river/creek, a scenic farm view, and massive indigenous rock structures that act as a natural agility course. (Please note: While our main in-ground pool with a waterfall is currently undergoing tile and coping renovations, our alternative Splash Zone pool is open and ready for action!) 🏡 The Base Camp (Backyard & Amenities) Wind down before or after your hike in our fully fenced backyard. Kick back in the shade on the comfortable leather couches beneath the gazebo (equipped with optional netting or solid enclosures), crank up your favorite playlist on the portable sturdy Bluetooth speaker, charge your devices, and help yourself to a complimentary snack or drink while your dog cools down and rehydrates. (Check our complete amenities list—we’ve stocked just about everything you could possibly need!) EXTRAS The Splash Zone ($5): An interactive splash pad featuring an attached 1.5-foot deep pool (depth can be lowered). Towels are included, along with waterless bath products and wipe-downs. Located inside fenced in area next to gazebo. Full Dog Wash Station 🛀 ($5): Hose attachment with adjustable pressure settings, hot and cold running water, a baby pool for a comfortable bathing space, and a wide selection of dog shampoos (including Aveeno and Johnson & Johnson baby shampoos). We also provide a rubber grip-handle scrubbing brush, conditioner, ear wash, fresh-scent spritzers, a waterproof collar and tether setup for secure leash tie-down during baths, and an electric nail grinder equipped with a heavy-duty diamond drill bit that never dulls and features bi-directional rotation (spinning in both directions) for easy use. If your dog struggles with itchy paws, we also offer our homemade soothing paw rinse to help relieve irritation. Keeping Cool at The Wildwood Retreat ($3): A powerful 45-inch industrial Heat Buster fan to keep your furry friends comfortable. It features a heavy-duty OSHA safety grate and is placed securely behind the safety fence—completely out of reach for ultimate peace of mind while delivering a refreshing breeze. The Dog Run: A secure dog run attached directly to the fenced backyard for easy, seamless transitions. Human Comforts: Dedicated storage space for your gear and easy access to an indoor restroom if needed. On the House: A refrigerator/freezer right by the gazebo couch stocked with fresh water for pups and bottled water for humans (plus flavor packets). We also provide collapsible travel bowls, hands-free water bottle straps and hiking bags, portable phone chargers you can take on the trails, sunscreen (including individual La Roche-Posay facial sunscreens), bug zappers (upon request), citronella candles, lint rollers, and plenty of dog waste bags! 🥾 The Wildwood Trails & Natural Agility Course Ready to explore? Head into the woods for an authentic hiking adventure on our mountain property. Our trail system features: The River Trail: Make your way through the trees on an uphill trek out to a beautiful river—and enjoy an easy downhill cruise on your way back! Scenic Overlook: Follow the property line out to a stunning view overlooking a local farm and preserved woods. Nature’s Parkour: Boost your dog's agility! Our 5-acre property offers a landscape unlike anywhere else in the region. Forget flat woods—you get steep slopes, rocky outcrops, and massive, ancient boulders that create a unique, three-dimensional maze for your dog to explore. It’s nature’s own jungle gym, full of rocky secrets waiting to be discovered! 🐾 Dip Your Paws In! Got a pup who is a little unsure about water? Skip the high-pressure splashes! Our calm river area is the ideal spot for timid dogs to take things at their own pace. With a gentle, natural entry, they can safely dip their toes in, explore the water's edge, and build up their confidence completely stress-free. ⚠️ Important Host Notes Property Setup: There is a home and a family shop on the property, but your trail and yard time is entirely your own private escape! Footwear: Because our trails feature authentic, natural mountain terrain with dirt, steep slopes, and rocks, proper hiking shoes or sneakers are highly recommended.

Christian's 7.6 Acre Unfenced Private Dog Park In Westtown

Doby Dog & Fishing Escape - 15 Acre Unfenced Private Dog Park, Pool & Pond In Mendham

- 15 acres - 3 fields with tall grasses to explore (these are mowed by a tractor intermittently throughout the season - feel free to message for updates - multiple cleared acres - trail - pool (additional cost) - fishing * - swimming for dogs in pond * **Pond will be under going routine treatment/maintenance from our management company this coming week (7/13)*** Property & fields will still be accessible, but swimming & fishing will not be available during this time. Please message for more up to date details. We are a newer spot & have been happy to offer our property for dogs & owners to enjoy and explore. We have plans to continue improving our property to make it even more enjoyable and appealing. This includes treatment and management of our pond (this will help with any overgrown of invasive species such as so many cattails and keep any algae and weeds at bay during the summer months to insure a clear swimming, boating & fishing environment), we will be clearing out more overgrown foliage near the front dam & adding a bridge to create an additional access point to field#2 on the opposite side of the pond (currently the main way to access this field is by walking around the back side of the pond), we will also be adding a small cabin (we will offer this to be rented out in the future and will not have Sniffspot on those days) & we will add benches to the opposite side of the pond for all to enjoy. We look forward to sharing this journey with you all!

Steve's 5 Acre Unfenced Private Dog Park In Westtown

Wildlife preserve and game farm

Connecticut Audubon Society

The Connecticut Audubon Society dog park, located at 2325 Burr St in Fairfield, offers a scenic trail for dogs to enjoy. The park is open from 10 AM to 3 PM, seven days a week. For more information, visit their website ctaudubon.org or contact them at 203-259-6305 or [email protected].

Park hours: 10 AM–3 PM 7 days per Week

Platt Farm Preserve

Platt Farm Preserve in Southbury, Connecticut offers a peaceful dog park with a trail for dogs and their owners to enjoy. The park is open from 6 AM to 8:30 PM every day of the week. Visitors can contact the park at 203-264-4441 for more information.

Park hours: 6 AM–8:30 PM 7 days per Week

5 Acre Unfenced Private Dog Park In Weston

Trees, ponds, and bike jumps! Lots of beautiful birds and flowers.

Hopeland Hound Haven

60 acres of forest and trails on a woodland preserve. Past our property is the Appalachian Trail. Canopy shade when there are leaves. There are little streams, logs, rocks and all sort of areas for digging, running, jumping and sniffing. There is an upper trail and a lower trail and they both loop together. Up the trail to the right is a deck with chair and table and supplies. You can watch your dog in all directions from this vantage point as they run free and smell all the smells of a forest.

Mike's Private Dog Park In Rock Tavern

Laura's Oasis

8.21 acres of trails under mature trees. Stay out of the sun and walk our trails with your furbabies. We have a beautiful kennel that you may use if you need to keep your pups separated.