The remnants of Fort George are physical reminders of the military conflicts in Maine prior to its statehood. Because the town of Castine occupies an important strategic position at the head of Penobscot Bay, British forces seized the town in June 1779 and built Fort George to establish their control over the lumber-rich region, which they renamed New Ireland.

Set on a rise above the Stroudwater River, the George Tate House is two-story Georgian-style structure. It is clad in unfinished clapboards and has a massive center chimney. The facade is symmetrical and a one-story ell extends off the east elevation. The centered entry door is framed by heavy pilasters supporting a pediment. The windows are made up of multiple small panes. The house's most unique feature is its roof: the gambrel form is recessed in front at the break in pitch and three small windows allow light into the attic behind them.

Located southwest of downtown Hallowell, the Elm Hill Farm consists of a farmhouse, garage, storehouse, and barn with farm fields interspersed with fences and hedges. The farmhouse is a modest dwelling with a side-gabled roof, two interior end chimneys, gabled dormer, and a central entry. The dormers and interior chimneys were added later to create additional space in the upper story. John Merrick constructed the house in 1799 upon his return to Hallowell from England after marrying Rebecca Vaughan.

Once a booming mill village, the Head Tide Historic District is now best represented by fourteen eighteenth-century and nineteenth-century houses. Of these fourteen, six were present at statehood, including the pictured Plummer House. Named after the furthest point upstream where a river is affected by tides, the district is situated on either side of the Sheepscot River and surrounded by hills.

Comprising much of Main Street, Whitman Street, Deering Street, and Danforth Street, the Norway Historic District includes the historic commercial and residential center of Norway. Main Street includes numerous commercial, industrial, and civic buildings constructed of brick or wood, while the intersecting cross streets boast mostly wood frame residential buildings. One of the oldest commercial buildings, the Leavitt Hardware Building (pictured center below) was constructed in 1816 with additions made in 1851. It is a modest two-story wood frame structure with a gable front roof.

Composed of five historic properties and situated on thirty acres of land, the Sedgwick Historic District is located on Route 172 at Old County Road north of Sedgwick proper and contains some of the earliest buildings constructed in Sedgwick. The Town House (pictured) was originally constructed as the Congregational Church in 1793. In 1849 religious services were discontinued at the building and the town voted to make the former meetinghouse the Town House. As a result, the town lowered the roof by ten feet and removed interior seating galleries.

Located on Burgess Road and one of the earliest houses constructed in this remote part of Maine, the Burgess House has had several additions constructed throughout the nineteenth century with all the components sheathed with clapboard siding with side-gabled roofs. The original structure is a one-story Cape with double-hung windows with numerous small panes of glass. Characteristics of a Cape are its low, broad massing with interior rooms placed around the large central chimney. The entrance is framed by five-paned sidelights and a louvered transom.

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.