Located on the west bank of the Sheepscot River on either side of U.S. Route 1, the Wiscasset Historic District contains an impressive concentration of pre-twentieth century civic, commercial, residential, religious, and funerary buildings, structures and sites. Wiscasset was first settled by European-Americans in the 1670s, but conflicts with Native Americans prevented further development until the mid-1700s. The deep harbor along the Sheepscot River proved a fortuitous location for a safe port and shipyards. The town gained further prestige when the local courts relocated here in 1794.

The Mitchell House, located in Yarmouth, is an excellent example of a Federal-style residence and was home to several noteworthy town residents. The large two-story dwelling sits on a granite foundation and has a steeply pitched hip roof with four brick chimneys. It is notable for its full height tapered fluted pilasters which provide emphasis on the center of the facade. The door is surrounded by a half-length sidelights, subtle entablature, and a fanlight with a unique decorative border and keystone.

The Chestnut Street Historic District is located south of Route 1 and west of Camden Harbor. The historic district consists of over 85 structures found on Chestnut Street, Wood Street, and Pleasant Street. European settlement in Camden began in the latter part of the eighteenth century and was centered around the natural harbor at the outlet of the Megunticook River. The Chestnut Street area was developed first, divided into four tracts of land, and granted to original settlers.

Situated near the Camden-Rockport town line, the Conway House is a modest-sized wood-framed Cape. The Cape was a popular residential building form in the 1700s and early 1800s and many of Maine's earliest houses were constructed in this manner. The Conway House exemplifies the Cape form of a side-gabled roof with a large central chimney and two rooms on either side. The roof line is low and the windows and doors are positioned close to the eaves. A small four-light transom is placed above the front door. The house is clad in wood shingles.

Originally built along the Piscataqua River for John Haggis in 1774, this Georgian-style house is an exceptional example of a Colonial era dwelling. The ornate structure has a steeply pitched hipped roof with flared eaves and a central entrance framed by a pedimented portico (or porch) supported by Doric columns. Author Sarah Orne Jewett lived and wrote in this house for most of her life. Born in 1849, she wrote over twenty novels and collections of short stories that are considered quintessential in their depiction of the lives and landscapes of rural Maine in the late nineteenth century.

Located on Main Street in Bucksport, the Jed Prouty Tavern and Inn is a three-story building overlooking the Penobscot River. It has a side-gabled roof and a one-story veranda that runs the entire length of the building. It has two entrances, both framed by sidelights and a transom. The oldest section of the building, the eastern end, was built by Asa Peabody and was only two stories with a hipped roof. In 1820 a man named Sparhawk opened a tavern and inn in the building and changed the roof to side-gabled.

Positioned on top of a slight hill overlooking the outlet of the Ducktrap River into Penobscot Bay, the George Ulmer House is a two-story timber-framed residence with a hipped roof and two interior brick chimneys. The house demonstrates the Federal style with its symmetrical front facade and delicate inverted cove brackets under the cornice . George Ulmer, a Revolutionary War veteran, arrived in Lincolnville in 1784 with his brother Philip, also a veteran. The Ulmers, through a variety of endeavors, amassed substantial wealth in a short amount of time, but subsequently lost most of it.

Lt. Robert Andrews commissioned his house from John Kilborn, Jr. a local master builder in 1805. The house, located south of downtown Bridgton in a rural area, is two stories with a side gabled roof and clapboard siding. The facade is symmetrical with a central entry. The entry door is framed by tapered pilasters supporting a finely denticulated cornice. Above the door is a leaded fanlight. The windows are made up of multiple small panes and have simple frames. The main cornice is also denticulated, identical to the one over the door.

The Paris Hill Historic District boasts a rare concentration of early nineteenth-century buildings in its compact village center. Much of Paris Hill's charm is due to its cohesive appearance as a collection of Federal and Greek Revival buildings; the built landscape remains largely-unaltered, with all but a few original buildings still standing. The arrival of the Atlantic & St.

Thought to be the oldest known house in Deer Isle, the Peter Powers House is located between Deer Isle and South Deer Isle and faces Long Cove. It was built at a time when maritime travel was more prominent than overland routes. The gambrel roof was a rare architectural feature in Maine, especially on a Cape form, which is traditionally side-gabled. The one-and-one-half story structure is sheathed in clapboard siding and sits on a fieldstone foundation. The house retains windows with small panes of glass. This modest house has a centered entrance with a paneled door.