As you head south of the city, there are some beautiful hilly areas which are perfect for a more endurance-based walk. You can also find several medium-intensity walking trails in this region as well. For a small town in Pennsylvania, this place really does have it all when it comes to dog walking!
Another great option is Upland Park which features a wide array of kids toys and play areas as well as walking and biking trails and several beautiful fields. It is also right next to Chester Rural Cemetery which is an old and beautiful cemetery with several walking paths.
This neighborhood also has two unique parks that show the area's rich history. The first is Deshong Park which is an old estate that was turned into a beautiful recreational park featuring a gallery displaying the former owner's vast art collection. The second is Veterans Memorial Park where you can pay respects at a beautiful memorial for all of our fallen veterans.