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Vincennes Circle
Access Point42.76458, -87.77751
Description
This is a popular spot for (stand-up board) surfers. I've been surprised to see them riding what they refer to as 'double-over-ankle' (a take-off on big-wave surfers who talk about 'double-over-head'), and they are apparently satisfied even when catching rides of only 5-10 seconds! (I won't generally suit-up unless/until I see rides of 20-30 seconds.)
Park curbside, carry down wooden stairs to a small sandy beach tucked between some jetties. The 'breaks' here tend to be fairly smooth and consistent.