Wellesley Hills is located on the northeast end of the downtown area of Wellesley. The area has a very long history, being first settled in 1630, but did not gain its current name until 1881. The area has worked hard to keep its old-world feel, making this area a treasure for walkers.
A main road that cuts through the neighborhood offers a few small businesses including restaurants and stores. You will need to head down into the heart of Wellesley to find pet stores, groomers, and veterinarians, however. It is a small price to pay for the small town feel of this area.
The Wellesley Hills area is subject to a lot of snow in the winter and January can be very cold. If you plan to brave the chilly weather, be sure your pup is properly protected. Still, there are 200 sunny days a year here, so make sure to enjoy the beautiful weather while it's around!
Wellesley Hills, of course, does have some hills, but the great thing about this area is that you can really choose your own terrain to walk on. There are also flat areas that are great for a casual stroll. You do not have to go far if you want more of a workout and you can choose from gentle inclines or more challenging hills.
The most common walking surface is asphalt or concrete. Many of the sidewalks are older but in good repair and many of them do have grass shoulders for your four-legged companion. There are also several dirt and gravel paths that cut through town with grass lining them. This is a great resource for walkers because it gets you off the concrete and onto something softer for your feet! These paths make a spectacular place to walk during the fall when the trees start to turn colors.
If the paths and their greenways are not enough, you are fortunate to have a generous amount of parks in this area. At the northeast end of town is Phillips Park, just off the Brook Path. Lots of green fields allow you to let your pup run a bit. Lots of trees also mean that there is plenty of shade.
The Brook Path ends right across the street from Issac Sprague Memorial Clock Tower, a historical landmark that offers a nice patch of grass and benches to take a rest on. Centennial Park offers lots of trails and grassy, wooded areas to explore.
Finally, Morton Park lays between downtown Wellesley and Wellesley Hills. In addition to the town hall building that sits within this park, there are paths, grass, and trees to enjoy. The town hall was finished in 1886 and its Romanesque design is on the US National Register of Historic Places.