Fort Edgecomb was constructed to protect Wiscasset - a critical port community and one of the busiest in New England in the early nineteenth century. Built at the south end of Davis Island, it overlooked both the Sheepscot River and Back River and provided an excellent vantage point to keep watch on approaching maritime traffic. The octagonal fort is modelled after English forts and is two stories tall. The walls of the first story, 27' feet high, are pierced by narrow openings so that muskets could be fired from the interior.

The Parson Fisher House is an uncommon example of the Federal style with its asymmetrical front facade with an off-centered entry. The two-story dwelling has a hipped roof with a substantial brick interior chimney. The full width beltcourse of flush boards above the second story windows is a rare feature for the time. This house is the second built by Parson Johnathan Fisher, but the gabled-barn behind the house likely dates from the construction of the original house in the late-eighteenth century.

A National Historic Landmark, the Parker Cleaveland House is a two-story frame dwelling with a low-pitched hipped roof and four tall brick interior end chimneys. It features a central entry on the front facade with a paneled door topped with an elliptical fanlight and flanked by pilasters and surmounted by a frieze and cornice. The residence is significant for its association with Parker Cleaveland, a nationally recognized mineralogist. Cleaveland lived here from 1806 to 1858 and was a professor at Bowdoin College.

Built for Nathaniel Dyer, a shipbuilder and merchant, the house is unusual as a modest brick home on the Portland peninsula. Other brick houses in Portland from this period were typically more elaborate. The front of the house is laid in Flemish bond, a pattern that alternates the long and short sides of the brick, while the other elevations are English bond, which alternates rows of the long and short sides of the brick. The facade is symmetrical with a central entry. The door is framed by wooden pilasters supporting a projecting piece of molding above a fanlight window.

Originally located on the other side of Main Street and further to the south, the Squire Chase House was built in the Federal style but was later remodeled in the nineteenth century with Italianate-style characteristics. The dwelling is two stories high with clapboard siding and a hipped roof. Attached is a long ell connecting to a barn-both with gabled roofs. The front facade is symmetrical with a central entrance framed by red glass sidelights and topped with a fanlight. The Italianate-style elements include the bracketed cornice and ornate rectangular cupola.

This McCobb-Hill-Minott House, located on Parker Head Road, is an exquisite Georgian style house with a hip-roof and central cupola sitting between two chimneys. The two-story dwelling has clapboard siding with central doors on both the southwest and northwest facades. Both entryways are framed by Doric pilasters and topped by a triangular pediment. Originally from Ireland, James McCobb came to the area in 1731. He gained considerable wealth in both lumber and commerce and built the house after acquiring roughly 1,000 acres.

Though currently located in the central business district of Portland, when first completed, the Wadsworth-Longfellow House had nearly unobstructed views of the Portland Harbor and the Back Cove. The building sits back from the street behind a cast-iron fence and a brick courtyard. It is three stories high, constructed of brick. The symmetrical facade contains little ornamentation except the arched windows on the first and second floors and the entry porch sheltering the door. Doric columns support a projecting pediment that covers a simple wood paneled door.

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.