Winslow Park

I go to Winslow nearly every day when I’m in Westport. Great trails. Extremely scenic. There’s also a cute little creek just off the trail. Perfect if your dogs need a place to cool down. The park has both an off and on-​leash area, so dog-​owners be advised. Snobby labradoodle owners seem to disregard this rule and let their giant dogs roam and jump on visitors, so if you’re not a dog fan, be aware. Most of the visitors here are responsible, but again, it’s Westport. There are some people who assume rules don’t apply to them. A lot of people don’t pick up dog waste and leave plastic bags/​garbage everywhere. Some people also tend to regularly bring their aggressive dogs and assume it’s okay because they are some fancy designer breed. My little dogs have been attacked by several greyhounds and Rhodesian ridgebacks at this park, so just make sure to always be aware and look for signs of aggression when new dogs approach. There are also several people that bring dogs here that aren’t fixed, so be on the lookout for that. Also, wouldn’t recommend bringing food in the off-​leash area. You will be hounded by dogs and chewed out by annoyed owners.
Negatives aside, this park is very enjoyable and relaxing. It provides the perfect outdoor atmosphere for both you and your canine. Perfect place to get a nice jog in or just get some vitamin d.

Am I the only one who got lost trying to find this place? Since the address on Unilocal is wrong (it’ll bring you close to the area but not to the exact location)!! And it’s at an awkward intersection! Anyway it’s an overall nice park (more like a human park then a dog park) but it’s an off leash area which is super nice! There’s no water available (no stream or bowls anywhere) except for a small water fountain at the start of the park so bring some if you decide to come! There’s lots of trails and large areas to run but most of the dogs I saw weren’t doing much and my dog ended up mostly playing with the birds! Overall a nice experience on a warm spring day!

Really nice, quiet park great for a workout.
Pros
So much green
Walking distance to many vendors
Right off Westport Ave
Bike riding or jogging
Trail
Great for families
Parking available
Site seeing
Cons
Dog owners need to properly discard waste
Overall great place to picnic, party, or exercise.

I stopped here with my dog en route to New York from Massachusetts. The park itself is enormous! There are lovely woodsy walking trails and open meadows. A large portion of it is off-​leash dog-​friendly, and my dog loved romping around in such a big space. They provided poop bags as well as several water fountains– always a sign of a good park in my opinion. I recommend if you are in the area and need a stretch break!

wide open space for pups to run around freely! water for dogs as well as humans, and plenty of poop bags for convenience.

Beautiful park to bring your dogs to. Nice clean picnic tables and benches. Plus a doggie water fountain and free poop bags. Trails into the woods and wide open spaces to play ball. Great place to bring your dogs to socialize. Highly recommend.

This is a GREAT park. So much space. Very well maintained. The off-​leash area is huge! I only wish it was fenced in. Even with the snow melting, it was not soggy.
Definitely a great people and dog friendly park.

Located adjacent to the Westport Playhouse, Winslow Park is a large, Westport-​owned park in the heart of the town. In addition to walking and biking trails, it has a picnic area, a large off-​leash area for dogs, fields, and gardens. It’s open from sunup to sundown, and it has its own parking lot (a plus in Westport).
It’s really more of a large abandoned farm estate than a park. It’s beautiful and perfect for dogs to run around in. There’s a watering fountain, some toys (but not many – bring your own), and nice benches scattered around the grounds. Nice touch: the benches are named in memory of people’s pets.
Very nice park.