Gargoyles are the original user-generated content: a stonemason with a sense of humour and a long time to sit on a scaffold. Atlas Obscura rounds up the ones that break the mould, which makes for a handy itinerary of buildings to stare upward at. Look for the ones that are clearly portraits of someone the carver did not like.

From the street it is a row of ordinary D.C. houses; inside it is a warren of galleries and courtyards packed with art and odd objects. The collection leans toward self-taught artists, many with New Orleans roots. Exactly the kind of place that rewards wandering without a plan.

Not a gallery so much as a workplace that happens to be hung floor to ceiling with art. Since 1983, patients at Creedmoor have had studios of their own here, and there is even a recording studio whose albums you can buy in the shop. An unlikely, humane place, and the opposite of a white-cube museum.

A building that grew by accretion over centuries, starting with a gate in 1189. The plot twist comes in 1338, when the French sacked a town with no proper walls and went straight for the wine cellars. The king was reportedly not sympathetic, which is the medieval version of a post-incident review.

Angus MacAskill stood 7 feet 9 inches, and the record books went out of their way to note that nothing medical explained it. A Hebridean emigrant who became an international celebrity and came home to a fishing village is a fine story, and a small cemetery on Cape Breton is a suitably understated place to end it. Bring a long tape measure.

Most rock art is safely ancient; what catches the eye here is how much of it runs right up through the 17th to 19th centuries, so European contact is recorded in stone from the other side. A national park you could walk into, with an archive lying on the ground.

Georges Nagelmackers is the man behind the Orient Express, which makes a quiet suburban cemetery an unexpectedly romantic stop. Atlas Obscura admits the neighbourhood itself is nothing special, which is exactly the kind of honesty that makes a detour appealing.

An Irish tower house with a longer memory than its walls. The pleasing oddity is the fragments of Ogham among the stones, so a late medieval lordly seat is carrying scraps of a far older script. It is close enough to Cork that a return trip would not need much planning.

Most wineries do not mark their premises with a yellow buoy. This one has been letting the Atlantic do the stirring since 2012, fifteen metres down, on the theory that swells make a fine agitator. Go for the view across the bay, stay to wonder who first asked whether the fermenter could be put underwater.

The Netherlands is compact already, and this museum in Beek-Ubbergen compresses it further into a lazy afternoon. The extras make it: badgers, expressionist architecture, and a patch of ground that stayed Dutch when most postwar annexations were handed back. Few places let you walk ten landscapes and a border footnote before dinner.

A very pleasing kind of sightseeing: no ticket office, no gift shop, just looking up. These are private devotions on public walls, built by householders rather than handed down by the Church, and some of the lamps are apparently still tended. A walk best taken slowly, at dusk, with a neck that can stand it.

The sort of street that rewards the slow walker: quiet, nearly car-free, and accidentally an architecture timeline. Medieval recycling at its finest, since the wall was gone but the foundations and the bricks were still perfectly good. Mind the residents, who live there and did not ask to be scenery.

Five minutes from the road and signposted, delightfully, by arrows laid out in rocks, each one different. The best detail is that visitors can peer through the opening at the foot of the great central slab, and squeeze between stones to reach the back.

A disused motorway stop is not an obvious pilgrimage, but this one was built for the transit route into West Berlin and dressed like a glam-rock stage set. The nicknames alone earn the detour. Few border crossings have ever looked quite so pleased with themselves.

The address alone, No. 27¼, is worth the trip. Tiny storefronts inside a Victorian market, each one tied to some piece of London's story, peered at through little windows. Exactly the sort of thing you walk past nine times, which is presumably the point.