My first big tour took in the town and region most important to Hopper's life and art: New York and New England. In addition to living in New York City from age 18 until his death, Hopper later in life summered in South Truro on Cape Cod in a studio he and Jo had built. As a student, he had painted at the New England sites that were de rigueur for artists at that time, such as Gloucester, Massachusetts, and Ogunquit, Maine.
From Maine lighthouses to New York's tenements, he surveyed the landscape and took his subjects from what surrounded him. Some of his most famous paintings are his New England lighthouses, like in Captain Upton's House, Lighthouse at Two Lights, and Lighthouse Hill. He also painted other coastal vistas like in Bootleggers, Ground Swell, The Long Leg, and 5 A.M. In industrial towns, he mined scenes like Freight Cars, Gloucester; Dawn in Pennsylvania; Sunday; and Office in a Small City. He captured on canvas quaint New England scenes like Portrait of Orleans and Sun on Prospect Street. On Cape Cod (an isolated piece of land jutting into the ocean), he was drawn to isolated houses like in Cape Cod Morning, Cape Cod Sunset, Mrs. Scott's House, Rooms by the Sea, Ryder's House, and Cape Cod Afternoon. He also portrayed lonely landscapes like Camel's Hump; Corn Hill, Truro; Cobb's Barn and Distant Houses; Hills, South Truro; New York, New Haven, and Hartford; and Portrait of Orleans. In old-money enclaves, he found the grandiose old houses he portrayed in paintings like Pretty Penny, Second Story Sunlight, Rooms for Tourists, and House by the Railroad.
Hopper wrote of the paintings of his friend Charles Burchfield (though he could have said the same about his own):
[Charles Burchfield's Street Scene]
"Our native architecture with its hideous beauty, its fantastic roofs, pseudo-Gothic, French Mansard, Colonial, mongrel or what not, with eye-searing color or delicate harmonies of faded paint, shouldering one another along interminable streets that taper off into swamps or dump heaps--these appear again and again, as they should in any honest delineation of the American scene."
Not only did New England provide subjects for his canvasses, but it seems to have tinged his view of things. He was a reticent and conventional man from an area full of such people. Perhaps the region's conservatism contributed to his paintings' sense of isolation. He often portrayed the local houses and their residents as isolated or sheltered. One such painting he titled Two Puritans. It seems he used such subjects to represent the aloofness and stifling morality of the region--and by extension the country's.