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.

During the early European-American settlement of Maine's towns, many areas were largely agricultural and animals including swine, horses, cattle, and sheep were allowed to roam free. As infrastructure improved and towns formed, the wandering animals became a health hazard and a nuisance. As a result, many towns constructed small pounds or enclosures to confine loose animals. The owner of the lost animal could then reclaim it from the pound for a small fee.

The Harraseeket Historic District is a large and amorphous district containing three villages, South Freeport, Porter's Landing, and Mast Landing, and outlying areas, such as Wolfe's Neck. The villages are situated on the Harraseeket River which river flows into Casco Bay. European settlers arrived in Freeport in the 1600s, but development did not increase until the latter part of the 1700s. Mast Landing developed first at the river's head of tide. As early as 1753 the British and local colonists had shipped lumber from here, particularly timber cut for ship masts.

The two-story, timber-framed, saltbox-plan, Pote House, located on Wolfe's Neck, faces an open field towards the Harraseeket River. Sheathed in split cedar shingles, the front facade has an odd number of windows and a right-of-center door-unusual for the time period and style. Originally built near Portland, the house was relocated to its current location c.1765 by its first owner Captain Greenfield Pote. Folklore notes that Captain Pote, a Yankee skipper, waited multiple days for a favorable breeze to set out to sea.