The Herbert in Kingfield, Franklin County, Maine is a small-town hotel associated with tourism in the Maine woods. The Kingfield House hotel was purchased in 1917 by Herbert S. Wing, heavily remodeled and reopened as the Herbert. The hotel is significant under Criteria A for its association with Entertainment / Recreation centered around outdoor pursuits like hunting, fishing, hiking, and skiing. The building is also significant under Criteria C, Architecture for its Colonial Revival style design and typical early twentieth century hotel construction.

The 1920 Hartford Fire Station in Augusta, Kennebec County, Maine is eligible for the National Register of Historic Places at the local level of significance under Criterion A: Politics/Government for its association with municipal fire protection services in the city of Augusta. It represents one period within the local city government's efforts to provide modern and efficient fire protection services to the community, as required under the city charter and ordinances.

The Tolman Cemetery is located in a built-up rural section of Rockland, Knox County, Maine. The cemetery was donated to the town by Isaiah Tolman in 1783 as the first public burial ground in the vicinity. The cemetery is significant under Criterion A for its association with early exploration and settlement in the area. The majority of graves dates from 1788 to 1850 and represents early families who settled the area. A large number of the graves are of early town officials, Revolutionary War soldiers and War of 1812 soldiers.

The Dark Harbor Shop on the island town of Islesboro, Waldo County, Maine meets National Register eligibility Criterion A, for its associations with commerce related to the development of the Dark Harbor summer colony on Islesboro. This summer colony is representative of the leisure time development that occurred along the coast of Maine in the last half of the nineteenth century, as middle and upper class urban residents sought to escape the summer heat and disease of crowded eastern cities for what they considered a simpler and more healthful way of life.

The Fives Court is a specialized recreation building located in Lovell, Oxford County, Maine. The building was originally constructed in 1924 as part of Westways Kezar a vacation and corporate retreat built by William Armstrong Fairburn. The complex was built on Kezar Lake near the White Mountains and a few miles from New Hampshire. Built in a Craftsman style with limited decorative details on the exterior, the one-story, one-room Fives Court interior reveals distinct characteristics common to this rare type of sporting court.

The Brick School is eligible for the National Register under Criteria A: Education at the local level, as an example of a community school that was enlarged and adapted to meet the changing educational needs of the South Paris community over a period of many decades. The rebuilding of the 1883 Italianate style Brick School in a restrained Classical Revival style in1940 reflected changing national standards for school construction and a trend toward consolidation of small (typically one room) neighborhood schoolhouses into larger buildings serving children from a wider area.

The Whittier Field Athletic Complex at Bowdoin College is eligible for the National Register of Historic Places at the local level under Criterion A, Entertainment and Recreation, as a collegiate athletic facility and under Criterion C, Architecture, as a significant and distinguishable entity whose components lack individual distinction. The grouping of the three major components (field, grandstand, and gate) along with related secondary elements (goal posts, scoreboard, flagpole, etc.) creates an identifiable historic district at the local level.

Keen Hall in Freedom, Waldo County, Maine is the last extant building associated with Freedom Academy which was authorized by a special act of the state legislature in1836 and continued to operate until destroyed by fire in 1957. The small rural village is proud of their educational heritage which included the only secondary academy in the county for many years. As a result of fires or deterioration, all other school and support buildings associated with the academy are gone as are one room and later elementary schools.

The North Monmouth Library is a one room Colonial Revival style building in the hamlet of North Monmouth in the Kennebec County town of Monmouth. Local architect Harry Cochrane of Monmouth designed the building in 1926 with construction complete in 1927. The building sits on a small corner lot donated by the Winthrop Mill Company. The predominately residential settlement retains manufacturing in the mill which sits south of the library with its associated mill pond. Local monetary, material and labor donations provided for the library building construction.

The Canadian Pacific Railway Depot, Greenville Junction, Maine is a well preserved example of a type of railroad building that was once common in Maine. Erected in 1889 by Canadian Pacific Railway (CPR), the Queen Anne style depot is located alongside the tracks of the CPR which is now owned and operated by Central Maine and Quebec Railroad. This depot once served as a junction between the Bangor and Piscataquis Railroad (B&P) and the CPR.