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We're on the North side and our favorite park is Sycamore. It's built on a landfill, so they can't plant trees, but they do have some shelters for shade. There are trees on the perimeter, so it's not completely barren. It's just under a mile lap around. They do have a small dog area, but small dogs are welcome in the main area too. The crowd is mixed but typically medium and large dogs. There's almost always someone there, even on the coldest days, and usually a good crowd.
Warner is great- wooded and open paths, natural swimming area, open fields. The only problem with Warner is that escape artists can occasionally find their way out (either along the river in the woods to the left as you come in the gate or right over the ice to the railroad tracks in the winter). They also have a small dog area. Warner is nice because it's in a very large park, Warner Park, which also allows dogs on the paths.
Cherokee Marsh is also very nice, it's pretty big with a floating pier for dogs to play fetch in the lake. It has woods and marshes and open fields. It's never happened to us, but I've heard that Cherokee can also be escaped by the determined dog. Cherokee also only has a single gate system and is on a busy road, which makes me nervous sometimes.
If you like to hike you can check out Governor Nelson state park, on the north side of Lake Mendota, about 2 miles from Cherokee Marsh on M. They have lots of trails, some in the woods and some in the open fields. Mellow, easy hiking with wide trails. You can hike on-leash, although you can get away with off-leash. We're often the only ones there or may meet one or two people on the path. They have a dog swimming area, where off-leash is allowed. Governor Nelson has marked Native American effigy mounds right off the trails, which I always like to check out when we're there.
They're also planning a new north/east side park and have it narrowed down to three locations, off of Aberg or off of East Washington. The west side may be planning more too, I'm not sure.
Notes about Madison parks: You need a permit, if I recall correctly it's about $20 a year with a break on the second dog (Gov. Nelson is a state park, so you need a different permit there). The parks don't supply drinking water, but do have bags. They've tightened up the rules on children and they need to be over 8.
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