Roughly encompassing sixty-three acres, the East Machias Historic District starts at the Pope Memorial Bridge and includes structures, both residential and commercial, on Bridge, High, and Water Streets. East Machias was settled in 1763, but trading posts existed in the area as early as 1633. After incorporation, East Machias became a shipbuilding and lumbering community with the first sawmill built in 1765. As the industries grew many prominent citizens, including veterans of the American Revolution and the War of 1812, built homes within the district.

Located on a rural road, the Stephen Longfellow House is a large Georgian-style side-gabled dwelling. The house is two stories high with a massive center chimney and a symmetrical facade. Located in the center, the door is topped by a transom and the entry is framed by a triangular pediment supported by pilasters. The windows are multi-paned and on the first floor are topped with wood molding. The second-floor windows sit directly below the eaves, which overhang slightly. On the interior, the house retains its original woodwork which includes floor to ceiling paneling in several rooms.

Located on Foreside Road, the Randall-Hildreth House is a two-story dwelling in the Georgian style with a low-pitched hipped roof with two symmetrically placed interior chimneys. The front faade has a prominent entryway with a six-paneled door surrounded by a transom and sidelights. Above the doorway is a compound-roof pediment supported by ornate columns, likely added by the late nineteenth century. Other unique features include detailed wooden quoins (mimicking stone block) at all four corners of the house and dentils under the roofline.

Originally located in York Corner, the school house is a small wood frame structure with a side gabled roof. The entry sits at the north side of the facade, with a small window just off center. The other elevations contain small windows and a chimney is located on the north elevation. The windows were originally covered in oiled brown paper, producing a dull, yellow light in the interior. Built by the residents of York, the school served the local children. It operated as a school for more than 100 years.

The Spring Street Historic District encompasses portions of the West End and the Arts District in Portland. It is a predominantly residential area with multiple churches and schools. The area was historically where many of Portland's wealthy citizens made their homes. Structures existing by 1820 are Federal-style brick townhomes, such as the Prentiss Mellen House dating from 1807 (pictured). The earliest settlement on the peninsula was established in 1632-33. Portland, like many early Maine settlements, experienced numerous conflicts with the Native American inhabitants of the area.

Situated on the east side of the Presumpscot River, the Great Falls Historic District consists of three residences and several industrial ruins. All three buildings are of frame construction and represent either the Federal style or the Greek Revival style. The oldest building is the Federal-style Trickey-John White House (pictured) that features a low-pitched hipped roof, clapboard siding, and a central entry topped with a louvered fan and flanked by sidelights.

This single-story Cape Cod style house is thought to be the oldest in Damariscotta. The structure is a good representation of the types of homes European settlers would construct after the initial wave of settlement. The Chapman-Hall House is thought to have been built by Nathaniel Chapman, half-brother of Anthony Chapman who is believed to be the first permanent European settler in Damariscotta. Nathaniel, an established housewright, was persuaded to leave Ipswich, Massachusetts, to construct proper homes to replace the rudimentary structures first constructed.

This Gothic Revival-style house is an unusual example from the early nineteenth century. Located on Whiskeag Road, this two-and-a-half story rectangular dwelling is constructed of granite blocks with wood trim and a gable roof. The facade has a centralized door with granite steps flanked by large floor to ceiling windows with many small lights topped with pointed arches. Known as the "stone house," this dwelling was built by one of the founding fathers of Maine and the state's first governor.

The Dyer-Hutchinson farm is one of the few eighteenth-century farms still in active use. The farmhouse, a one-story Federal period cape, was built by William Dyer in the western part of Cape Elizabeth. The property served as his homestead, where he and his wife raised two children and owned forty-five acres of land, twenty of which were used for farming.

The oldest part of the Squire Tarbox House, the current one-and-a-half story rear ell, was built in 1763 and located on a hill to the north. In 1806 Squire Tarbox purchased the house and moved it in 1819 to where it now resides. The next year, he constructed the two-story part of the house. This two-story main block is characterized by the Federal style with a low-pitched hipped roof and symmetrically placed window and door openings on the front facade.