Wharf Street

Because the Old Port is notorious for its drunken shenanigans, it is also well patrolled by Portland's boys (and girls) in blue. If you're not sure whether you've over-indulged, or just want to prove to the cops that you're perfectly sober, the best place to check is on Portland's historic gauntlet: Wharf Street. The cobblestone pavers are perilously rounded and separated by crater-size gaps, perfect for snagging heels of all sizes. Even men, with their practical footwear, misstep across the cobblestones, but it's the women, who despite their best Sarah Jessica Parker impersonations, find walking Wharf Street a sobering experience.

If you'd rather some free entertainment than such a public challenge, there are several great spectator spots. For the best action, stick close to the trifecta of the college-bar scene: Iguana, 51 Wharf, and Oasis, where you're most likely to spot some unsteady stilettos. If you're uncomfortable being that shadowy character, the outdoor patio at Amigo's offers a great viewing gallery — and lets you enjoy a beer at the same time. If Amigo's is too far, the outdoor area at Gritty's throws you right in the action, providing a place to cheer (or heckle) the poor souls stumbling along on their cobblestone crusade.

Wharf Street | if you can find it, you don't need the field-sobriety test

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