Some skate spots will always be intimidating. The gap might be big, the rail steep, the staircase long, or the transition so tight it can barely be negotiated. Whatever the case, every new trick landed at these storied spots is canonized, setting skating’s bar ever higher. Some of these spots are no more, but their legends loom large, in part because we wonder what might be accomplished had they not met their fate too soon. No matter how much skating changes—and it’s come a long way since many of these locales were first skated—they will always serve as markers of its progression. Here are 10 of the most challenging skate spots of all time.

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