As you walk along the streets in Westchester you will find that there are a variety of stores and restaurants should you need a drink or a snack along the way. There is one small park in the community near many of these amenities, so once you have done your shopping you can you stop by the park to give your furry friend a chance to roll in the grass. The weather here is the same as the rest of New York City; walking is possible through most of the spring, summer, and fall with winter being variable depending on how cold it is and how much snow is on the ground. Be aware that summers can be quite hot and humid, so early morning or evening walks might suit you better than a midday hike.
Westchester is primarily flat, with little in the way of hills--this can be either a blessing or a disappointment. If you and your dog are just starting out then the lack of hills might be just what you need, but as you get a bit fitter, you might find yourself looking for more of a challenge. You will find that the immediate neighborhood does not offer anything more than sidewalks made of concrete for walking, so if you want to walk someplace easier on your dog’s feet or with a more natural feel you will need to be prepared to do a bit of traveling to get there. Fortunately, in New York, you never have to go too far to find some open grass to sink your paws in! To the east about 1.5 miles is Pelham Bay Park, which has plenty of trails and a saltwater shoreline that makes a great change of pace for you and your companion.
Finding greenspaces to take your dog is a bit of a challenge in this neighborhood. The Owen F. Dolen Park has a bit of green grass, but not really enough for anything more than a quick stop for a rest and some shade. If your dog is begging for some grass and other greenery, a better choice lies east at Pelham Bay Park. Not actually in Westchester, this park is the largest park in New York City and boasts miles of trails and shorelines as well as wide swaths of green grass and trees for Fido to explore. You will also find an off-leash area where your dog can romp free and enjoy the company of his friends. The only other greenway large enough and close enough to be a practical option is the Soundview Park on the Bronx River. The park has plenty of grass and places to walk and play, but it is 3 miles away and you will likely want to take a car ride to get there.