Richard Manning, a native of Salem, Massachusetts, moved to the Casco area to manage his family's large land holdings in the area after his father died in 1813. His sister, Elizabeth Clark Hawthorne, followed her brother to Maine along with her son and future author, Nathaniel Hawthorne. It is believed they spent some time at the house before moving into their own located a short distance away in Raymond. The Richard Manning House is a two-story wood frame dwelling, sheathed in clapboards with a shallow pitched hip roof, and two large interior chimneys.

Built by Joseph Woodman, a prominent local builder, for Dr. Royal Brewster, the house is a finely detailed Federal-style structure in a rural setting. It is a two-story, clapboard-sided house with a low-pitched hip roof and two end chimneys. The facade is symmetrical with a central entry. The door is flanked by sidelight windows and topped by a recessed arch. The entry is sheltered by a Greek Revival-style porch, a later addition. A simple band of wood separates the first and second floors. The denticulated cornice sits above a section of unusual zig-zag trim.

Sandwiched between Route 2 and the St. Lawrence and Atlantic Railroad tracks, the Peabody Tavern served as a stagecoach and later a railroad stop between Portland, Maine, and Lancaster, New Hampshire. It was built by Thomas Peabody, of Andover, Massachusetts, whose family was one of the first who settled the area. The tavern is a simple wood-frame, 2-story structure with an asymmetrically pitched side-gabled roof. A large ell extends off the rear on the east end of the main building. The facade is symmetrical with double-hung multi-paned windows.

Located just southeast of Windham Center, the Goold Family House is significant for its association with William Goold, a notable Maine author and historian. He was born at the farmstead in 1809 (though likely in a different house). He was a member of the Maine Historical Society and delivered fourteen papers before the society from 1873 to 1889. He also published a column in the Portland Press Herald and published a history of Portland, Portland in the Past. Goold served as a state senator from 1874-75. The house has undergone several additions since its construction.

Located northwest of Back Cove, the John B. Russwurm House is a two-story, wood-frame structure with a side-gable roof. Sheathed in clapboards, it features a symmetrical facade with a central entry door. The door is framed by a later Greek Revival-style surround of sidelight windows and pilasters supporting a wide entablature. The second floor windows sit just below the eaves. The two interior chimneys are located below the gable peak on the rear of the house. Russwurm was the son of a British Jamaican plantation owner and an enslaved women.

Containing one of Maine's earliest existing homes, the John Sedgley Homestead illustrates the evolution of a colonial era homestead. It is made-up of a variety of structures, including a c.1715 cape (pictured), farmhouse, carriage house, stable, and two additional outbuildings. John Sedgley was gifted the land by his father-in-law after marrying Elizabeth Adams. The cape was constructed as the couples first home. It is a low-posted, one-story dwelling with a side-gabled roof, sheathed in clapboards. The facade is asymmetrical with the entry just off center.

Brickett Place, located on Evans Notch Road (Route 113) in Stow, is an uncommon example of a Federal-era brick farmhouse. It was built by John Brickett using locally fired bricks and hand-hewn timber for his family, which grew to include nine children. The house features simple details such as flat brick arches over the windows and a three-light transom above the entry door and is distinctive for its almost square footprint. Brickett came to Maine from New Hampshire in c.1803. He built his house before purchasing the land it occupied. He eventually purchased it and 50 acres in 1820.

Located on either side of Route 25 just before its intersection with Route 35, the Standish Corner Historic District consists of four buildings dating from the late eighteenth and early nineteenth centuries. A fifth house that was originally part of the district has been demolished. The buildings in the district are similar in scale, orientation, and setbacks from the road. Wood framed and sheathed in clapboards, all were originally residences. Their facades are symmetrical with central entries. The Daniel Marrett House is the oldest, built in 1789, and now a museum property.

Located north of Birch Point looking out into Machias Bay, Fort O'Brien dates to the Revolutionary War and its first naval battle. A few weeks after the shots at Lexington and Concord were fired, the British ship Margaretta escorted a Machiasport shipowner, Ichabod Jones, to the fort to ensure he returned to Boston with lumber needed for the construction of barracks. The townspeople, led by Jeremiah O'Brien, retaliated and captured the Margaretta. A few weeks later the British sent reinforcements.

Job Burnham built this tavern on Main Street. It looks much like it did in 1770. It is two stories tall with a gambrel roof and central chimney. The tavern sits on a stone foundation overlooking the Machias River. Its yellow paint and clapboard siding are appropriate to the colonial era as are the small panes of glass in the windows and above the door. The gambrel roof is indented with small windows on the second story. The tavern was constructed seven years after the first settlers arrived in Machias and played a role in the American Revolution.