Fort Sullivan was built to protect the small fishing settlement and aid in the enforcement of embargoes against the British. The site was considered the easternmost boundary of the United States and sat on a bluff on Moose Island at the mouth of the St. Croix River. The fort was roughly five acres and consisted of three batteries, three blockhouses, a store magazine, an artillery storehouse, and an unfinished regent's redoubt. On June 1, 1812, President James Madison declared war on Great Britain. Two years later, the British formed a naval blockade of New England ports.

Located on Lawrence Road, the Jacob Randall Homestead includes a two-story brick dwelling that sits on a granite foundation and has a side-gabled roof with two symmetrically placed interior chimneys. The central entryway consists of a recessed door topped by a fanlight. A one-and-a-half story brick ell is attached, but it is unknown when it was constructed. Randall came to Pownal in 1796. Originally from Weymouth, Massachusetts, he purchased 105 acres that included land on both sides of the Chandler River.

John C. Todd likely built this house, which may be the oldest residence in Eastport. The side-gabled house has a large central chimney with its rooms arranged around it, a form often referred to as the Cape form. It has wooden clapboard siding and a plain wooden front door with a transom window above. The windows on the front facade are placed tight under the eaves. The rear ell features a jog, a shed-roofed addition sheltering an entrance, likely to the original kitchen. Eastport was first settled in 1772 by fishermen from Newburyport, MA, and Portsmouth, NH.

Located on the Fore River, Stroudwater was founded by Colonel Thomas Westbrook in 1727 as a landing for shipping masts to England. The Stroudwater area eventually grew to include lumber mills, a tannery, and various stores. After the Cumberland and Oxford Canal was completed in 1830, connecting the Fore River with Sebago Lake, the village became a bustling trade center. Manufactured goods and groceries from Portland were shipped through Stroudwater to the interior.

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.