Here are some picture postcards of the inspirations for the story “The Strange High House in the Mist” (9th Nov 1926), inspirations which Lovecraft confirmed in letters. The story itself is set in the massive ‘dream-cliffs’ above Kingsport.

Postcard caption: “Eastern Point Lighthouse at the “Mother Ann” cliffs at Gloucester, Massachusetts [about 100 miles NE of Providence]. Mother Ann is a rocky cliff at the far south end of Eastern Point, near the lighthouse.”

Note the profile-figure of a recumbent woman, made by the outline of the rocks against the sky. Presumably this is “Mother Ann”.

Some of the cliffs they love, as that whose grotesque profile they call Father Neptune … — The Strange High House in the Mist

Lovecraft also writes in a letter that he had…

obtained a bit of natural grandeur on the cliffs at Magnolia, where the ocean pounds in supreme splendour at the historic rock of Norman’s Woe Rock

Postcard caption: “Rafe’s Chasm [on the cliffs very near Norman’s Woe Rock] is a remarkable fissure cutting into the sheer rock ledge at Magnolia. It is 200 feet long and 60 feet deep and into it the sea continually roars. From here you can obtain a marvelous view of the open ocean, “Kettle Island”, the Salem shore line and a glimpse of Marblehead.”

Suddenly a great chasm opened before him, ten feet deep, so that he had to let himself down by his hands and drop to a slanting floor, and then crawl perilously up a natural defile in the opposite wall. So this was the way the folk of the uncanny house journeyed betwixt earth and sky! — The Strange High House in the Mist

Here’s an interesting painting of Monhegan Island, Maine, by J. Perry Wilson in the late 1930s, which gets closer to the sort of setting I imagine for the story…

The island as long been a haunt of artists (see the books The Art of Monhegan Island, and Monhegan, the artists’ island), and one wonders if Lovecraft might have seen similar pictures in the 1920s?

Edward Henry Potthast’s “Hilltop (Monhegan Island)”, circa. 1925, is also evocative of the story…

All around him was cloud and chaos, and he could see nothing below the whiteness of illimitable space. He was alone in the sky … — The Strange High House in the Mist