Located south of Route 117 on Mountain Road in rural Oxford County, the Churchill Bridge is a rare surviving eighteenth-century span. The bridge is composed of dry laid stone, including five large rectangular slabs laid side to side. It is approximately twenty feet long and ten feet wide and the opening over Bennett Stream is approximately seven feet. The Churchill Bridge exemplifies common bridge building practices in the late eighteenth century, where the abundance of large slabs of stone in New England provided settlers and farmers with material for crossing small to modest waterways.

The Alna Meeting House is a two-story building set on a hillside facing south towards Wiscasset. When constructed it was located in the North Precinct of the larger town of Pownalborough (now Dresden) before Alna was incorporated as New Milford in 1794. Centrally located, it served those living in the villages of Alna Center, Head Tide, Puddle Dock, and points beyond. Constructing a meeting house was one of the most important tasks a burgeoning community would take on.

The Samuel Bucknam House is a Cape form with a side ell and Federal-style details. The most notable Federal-style detail on the house is the ornate carving found around the front entry. The front door is flanked by sidelights, topped with a delicate fanlight, and further emphasized by narrow Doric pilasters. The outermost pilasters support ornate urns carved in relief.

Located south of downtown Hallowell on a hill overlooking the Kennebec River, the Vaughan Homestead was the estate of Benjamin and Charles Vaughan, whose grandfather was Hallowell's namesake. The homestead consists of the main house, summer house, barn, gate, terraced garden, and lawns. The house was originally constructed in 1797 and was a two-story hipped roof building with four rooms on each floor and four chimneys. In the early nineteenth century a front porch and two-story rear ell were added. Later additional wings were added including a two-story octagonal one on the west side.

Located in Kittery Point, the William Pepperrell House was rumored to be the finest house in Maine at the time it was built. The house has been remodeled several times, first in c.1720 and then again in 1848 and no description of its original appearance exists. It is currently two stories high, with clapboard siding and a gambrel roof. The former primary entrance, facing Pepperell Cove, consists of a highly ornate surround of a broken pediment with a wood carved pineapple mounted in the center.

Serving as a general store from its construction until the 1930s, Elden's Store is a rare example of a commercial brick building in a rural area from the early nineteenth century. The building is two-stories high with a side-gable roof. The brick is laid in English bond, a pattern of alternating the long and short sides of the brick. The gable ends are clapboard sided. The windows have multiple small panes and granite sills and lintels. The building sits on the corner of Long Plains Road and Haines Meadow Road and has two street facing sides.

The Dr. Moses Mason House is a good example of the Federal style. Built facing the Bethel Common, the house is side gabled with clapboard siding. The facade is symmetrical with a centered entry. The door features sidelight windows and is topped by an elliptical filled fanlight. Pilasters supporting a band of molding frame the entry. Two internal chimneys are placed on the rear side of the roof. The front hall and stairway of the house contains Rufus Porter style murals, attributed to Jonathan D. Poor, a nephew of Rufus Porter, a prolific mural painter.

The Bucknam House, located on Main Street, is a rectangular residence that stands at two stories tall and is sheathed in wood shingles. It has a side-gabled roof, thick central chimney, and little ornamentation, except for narrow pilasters around the central front door. The front door is also topped with a five-light transom and a projecting cornice. This early residence retains windows with numerous small panes of glass. John Bucknam built the house when Columbia Falls was largely unsettled.

The Brown-Pilsbury Double House, located on Franklin Street, is a two-story Federal-style frame building with clapboard sheathing and a gable roof. It is referred to as a double house because it housed two families with prominent entrances on the gable ends of the house. Both units are near identical with a tight spiral staircase near each entrance. Each exterior entry features an ornate door surround of capped pilasters and entablatures.

Positioned on a ridge above McWain Pond with a view of rocky fields and Mount Tire'm in eastern Waterford, the McWain-Hall House is a Federal-style building with minimal ornamentation. The side-gabled house has a large central brick chimney and its windows are irregularly spaced on the front faade. A narrow transom window is placed above the central front entry. The windows are modest in size and are composed of numerous small panes of glass. David McWain, the first European-American settler in Waterford, arrived here in 1775 and began acquiring land.