Ram Island Ledge Light

Fort Levett was a former U.S. Army fort built on Cushing Island, Maine, beginning in 1898. Located in Cumberland County, Maine, in Casco Bay near Portland, Maine, the fort was heavily fortified with guns for coastal defense. Conceived under the Endicott Program in 1885 and begun in the wake of the Spanish–American War, Fort Levett was manned during both world wars. It was part of the Coast Defenses of Portland, later renamed the Harbor Defenses of Portland, a command which protected Portland's port and naval anchorage 1904-1950. The fort's name is sometimes misspelled as "Fort Leavitt".

The Eighth Maine Regiment Memorial, now the 8th Maine Lodge, is a historic summer fraternal meeting house at 13 Eighth Maine Avenue on Peaks Island, an island neighborhood of Portland, Maine. Built in 1891 as a reunion site for veterans of the American Civil War 8th Maine Volunteer Infantry Regiment, it is a fine example of Shingle style architecture, and an important work of the local architectural firm of Fasset and Tompson. It was listed on the National Register of Historic Places in 2006, and presently operates as a summer lodge and museum, with rooms rented to the public.

Portland Head Light is a historic lighthouse in Cape Elizabeth, Maine. The light station sits on a head of land at the entrance of the primary shipping channel into Portland Harbor, which is within Casco Bay in the Gulf of Maine. Completed in 1791, it is the oldest lighthouse in Maine. The light station is automated, and the tower, beacon, and foghorn are maintained by the United States Coast Guard, while the former lighthouse keepers' house is a maritime museum within Fort Williams Park.

The Fifth Maine Regiment Community Center is a historic building at 45 Seashore Avenue on Peaks Island, an island neighborhood of Portland, Maine in Casco Bay. It was built in 1888 by American Civil War veterans "as a memorial to their deceased comrades and as a reunion hall for themselves." It was listed on the National Register of Historic Places in 1978 and designated a Greater Portland Landmark in 1984. Today it is open as a museum.

Annie C. Maguire was a British three-masted barque sailing from Buenos Aires, Argentina, on 24 December 1886, when she struck the ledge at Portland Head Light, Cape Elizabeth, Maine. Lighthouse Keeper Joshua Strout, his son, wife, and volunteers rigged an ordinary ladder as a gangplank between the shore and the ledge against which the ship was heeled. Captain O'Neil, the ship's master, his wife, two mates, and the nine-man crew clambered onto the ledge and then, one by one, crossed the ladder to safety. The cause of the wreck is puzzling, since visibility was not a problem. Members of the crew reported they "plainly saw Portland Light before the disaster and are unable to account for same."Today, letters painted on the rocks below the lighthouse commemorate the wreck and the Christmas Eve rescue.

Cushing Island, or Cushing's Island, is a privately owned island in Casco Bay in the U.S. state of Maine. Part of the city of Portland, roughly 45 families live there seasonally.

Fort Williams Park is a 90-acre park in Cape Elizabeth, Maine, encompassing numerous historical sites. Perhaps most famous for having Portland Head Light on its grounds, the park also encompasses the decommissioned and largely demolished United States Army post Fort Williams, which was operational during World War I and World War II.

Fort Williams is a former United States Army fort in Cape Elizabeth, Maine which operated from 1872 to 1964. It was part of the Coast Defenses of Portland, later renamed the Harbor Defenses of Portland, a command which protected Portland's port and naval anchorage 1904–1950. After its closure, it was redeveloped into Fort Williams Park.

Greenwood Garden Playhouse was a theater on Peaks Island, Maine, United States. Completed in 1884, as an open-air roller skating rink, it was converted to a theater in 1898. It became a dance hall prior to its closure in 1957 as a summer stock theater. Jean Stapleton's first professional appearance in the summer of 1941 was in a production at the playhouse. Martin Landau also made his professional stage debut in a 1951 production of Detective Story at Greenwood Garden, where for several seasons he was a resident cast member. Its grounds featured a carousel, a Ferris wheel and a wooden observation tower, which people paid to be able to view Mount Washington, the highest mountain in the Northeastern United States. The playhouse was located on Garden Place, just off Island Avenue, near the southwestern tip of the island. In 2021, the garden was added to the National Register of Historic Places.

The C.A. Brown Cottage is a historic summer house at 9 Delano Park in Cape Elizabeth, Maine. Built in 1886–87, it is a fine local example of the Shingle Style then popular for such properties, and is an important mature work in that style of Portland architect John Calvin Stevens. The house was listed on the National Register of Historic Places in 1974.

The Umbrella Cover Museum in Peaks Island, Maine is a museum that pays tribute to umbrella covers. The museum was created and is curated by Nancy 3. Hoffman, who has collected more than 2000 umbrella covers from 66 countries as of July 2018.The mission of the Umbrella Cover Museums states that it is "dedicated to the appreciation of the mundane in everyday life. It is about finding wonder and beauty in the simplest of things, and about knowing that there is always a story behind the cover."The idea for the museum came when Hoffman was cleaning out a closet and came across seven umbrella covers. The museum began in Hoffman's kitchen and was moved to a larger location as the collection grew. The museum's collection ranges in size from a two-and-a-half-inch Barbie doll cover to a six-foot patio umbrella sleeve. It has hosted special exhibitions including “People and Their Covers” and “New Umbrella Cover Fashions.”On 7 July 2012, Guinness World Records named Hoffman's umbrella cover collection of 730 at the time to be the largest in the world.The museum is closed during the winter. Guided tours include Hoffman, who is also a musician, singing "Let a Smile Be Your Umbrella" while playing an accordion.

Peaks Island is the most populous island in Casco Bay, Maine. It is part of the city of Portland and is approximately 3 miles (4.8 km) from downtown. The island is served by Casco Bay Lines and is home to its own elementary school, library, and police station. It is the only island in Casco Bay that allows cars throughout the island due to its size. While small, the island hosts a variety of businesses including an ice cream parlor, restaurant, grocery store, kayak rentals, golf cart rentals, art galleries, the Fifth Maine Regiment Museum and the Umbrella Cover Museum, among others.The island was originally known as Pond Island. It became Michael's Island, after Michael Mitton was gifted the island on a sixty-year lease by his father-in-law, George Cleeve. It was subsequently named Munjoy's Island (for George Munjoy) and Palmer's Island (for Munjoy's son-in-law, John Palmer).