While it may no longer serve as an educational facility, the Red Brick School in Wiscasset remains a significant example of Maine's pre-statehood ties to Massachusetts. According to a 1647 law passed by the Massachusetts legislature, communities of fifty families or more were required to provide for the education of their children through the establishment of schools. The construction of the Red Brick School in 1807 marked the first offering of secondary education in the community, reinforcing the education that local youth received in grammar schools.

Located on North Main Street, the Robert Carleton House is one of the oldest surviving dwellings in Piscataquis County. Its later Federal style was a sophisticated choice considering this area was newly settled at the time it was built. The house is rectangular and two-and-a-half stories high. The central door is framed by sidelights and pilasters with an entablature displaying intricately carved fretwork. The house likely had a substantial central chimney that has since been removed. During the early 1800s milling became a significant industry in the area.

Located in the village of Goodwins Mills in Dayton, the Levi Foss House features the Federal style with later Greek Revival-style additions. The timber-framed dwelling is one story with a gable roof and a side ell that includes a shed and barn. The entire structure is sheathed in clapboard siding except for the rear wall of the ell which has wood shingles. The central front entrance is contained in a pedimented vestibule and is framed with pilasters and sidelights. Other features include a Greek Revival-style cornice at each end of the barn and moldings around the windows.

Likely the oldest surviving meeting house of the Society of Friends in Maine, the Casco Friends Meeting House is a modest one-story building sheathed in clapboards. The roof is front gabled and there is a small lean-to projection on the south elevation that contains the entry. Two small windows sit in the center of the facade, one in the gable. All trim is plain and the building contains no ornamentation except for narrow cornerboards and cornice returns.

Developed around a ferry crossing on the Kennebec River, Days Ferry is an intact rural late eighteenth- and early nineteenth-century village. This area of Woolwich was initially settled by European-Americans in 1638 and a trading post was established by Richard Hammond. The post was destroyed in 1676 during King Philip's War and was not rebuilt. The ferry between Woolwich and Wiscasset was in operation by 1750 with the Day family in charge of it in the 1780s.

Designated a National Historic Landmark, the Lady Pepperrell House is an excellent example of the High-Georgian style in New England. It is two stories high, sheathed in clapboards, with a hipped roof. The facade is symmetrical and dominated by a full height projecting center bay that contains the entry. The entry is sheltered by a hood molding supported by large brackets. Between the brackets and over the door is a panel carved with a delicate vine motif. Rising on either side of the door are fluted Ionic pilasters that support a pediment.

Located in a rural area east of Buckfield proper, the Enoch Hall House is a one-story frame building with a side-gabled roof and a large central chimney. The house has a symmetrical front facade with a central entry flanked by two windows on each side. The front door and its sidelights are framed by pilasters with delicately carved pointed arch capitals. Enoch Hall settled here in 1783 and originally constructed a log house.

Located in the southern part of Winslow, the Brick School is one of the oldest surviving district schools in the state. It is a single-story brick building with shingles in the gable ends. The facade faces south, with the entry door on the west and two windows on the east half. This southern facing orientation would have allowed maximum use of sunlight throughout the school day. The interior is made up of a single classroom with a small coatroom and fireplace on the west end. The school was constructed sometime between 1799 and 1820 and was part of School District No.

The Cherryfield Historic District is a discontinuous area approximately seventy-five acres in size resting on both sides of the Narraguagus River. Located on Route 1 and framed by secondary roads Routes 182 and 193, there are fifty-two contributing and ten non-contributing residential and commercial buildings that represent a wide selection of architectural styles roughly beginning in 1790 to 1947. Due to the proximity of the river, Cherryfield flourished as a lumber milling and shipping center.

The Blazo-Leavitt House is an excellent example of a Federal-style residence in rural Maine. It was built by Daniel Blazo, the son of a shipbuilder and merchant of French descent from Portsmouth, New Hampshire. It is believed he hired ship carpenters in Portsmouth who were unemployed by the Embargo of 1807 (which was enacted to protect American sailors, but unfortunately greatly curtailed trade in the North Atlantic). The carpenters completed elaborate interior woodwork and features including intersecting central hallways with arched ceilings.