Great Northern Railway Depot: Built in 1894, the year after the tracks were completed the Depot was originally located on the south side of the line. During an expansion of the rail yard in 1922, the building was moved to a location on Railroad Ave and enlarged to include a freight room. No longer an active depot, it is now owned by the City of Skykomish and will be the center of a new community complex. Listed on the National Register of Historic Places and the Washington Herritage Register, it is one of the last wood frame Great Northern depots remaining in the state.

Cascadia Hotel: The Cascadia, originally the Hatley Hotel, was built in 1922 on the site once occupied by Martin's Boarding House. A fire in 1937 destroyed the second and third floors of the hotel and only the second story was rebuilt.

Skykomish Community Church: King County records indicate this building was constructed in 1939. Local sources say the structure dates from even earlier and was originally built as a residence and later converted for church use. Remodels in the 1950's and 1990's have given the building its present form.

Skykomish Town Hall: This building was a former Great Northern Railway storage building once located south of the tracks. In the 1930's it was moved to its present location to serve as a town hall it was remodeled as a New Deal WPA (Works Progress Administration) project.

Olympia Tavern: The Olympia Tavern was opened in 1897 by Patrick McEvoy, a Great Northern Railway engineer. McEvoy was at the controls when the first passenger train crossed the summit in 1893. The original building was destroyed in the 1904 fire and was rebuilt in 1905. During prohibition it was known as the Maple Leaf Confectionary. It reverted to a saloon in 1933 and was renamed the Whistling Post. A robbery and arson fire on April 10, 2012 destroyed the building but by January 27, 2013 it was back up and running again.

Perhaps Skykomish's most prominent building, the Skykomish Hotel was built in 1904 on the site of an earlier hotel that burned to the ground. A magazine article published shortly after the new hotel was completed described it as "a fine four-story hotel, built by D.J. Manning, costing $10,000." In early years the hotel served travelers on the Great Northern Railway and was a well-known tourist destination for visitors seeking the area's magnificent fishing and hunting.

Maloney's General Store: Built by town founder, John Maloney, in 1893, this building for many years housed the town's general store and post office. With its typical Western Boomtown facade, the building began as a single 30 by 60 foot room. As the town grew, Maloney prospered and east and west wings were added. In addition to being a local landmark, it is listed on the National Register of Historic Places and the Washington Heritage Register. It is now the home of the Skykomish Historical Society.

Maloney's Warehouse: This building originally sat alongside the railroad tracks, across the street and slightly west of its present-day location. It served as an ice house and warehouse for John Maloney's General Merchandise, with goods being transported in and out of town by freight train. In the early 1920's it was moved to its present day location, and not long after converted for use as a movie house which operated until about 1969.

Manual Training Building: The Manual Training class of the Skykomish School built this building in 1922 as a school project. Formerly located one block west, it was moved to this location when the present day school was built. In 1954 it was purchased by the Town of Skykomish to serve as a fire hall. Today it houses the Town's maintenance department.

Worker's Cottage: Dating from the 1890's, this modest dwelling is typical of an early Skykomish worker's cottage. Originally just one room, a kitchen and bathroom were later added to the rear of the house.

Teacherage: Known locally as the Teacher's Cottage, this circa 1915 residence of Craftsman design originally housed single, female teachers employed by the Skykomish School District. It is now the home of the District's Superintendent.

Skykomish School: The Skykomish School, constructed in 1936, is one of seven schools built in Washington State under President Franklin Roosevelt's Works Progress Administration. Under the program, the community provided the concrete and lumber from local sources, and the WPA provided the labor. The building was designed by architect William Mallis and it replaced a two story, wood framed schoolhouse on the same property. The three story concrete building has streamlined Modern detailing and Art Deco ornament. Although utilitarian in appearance, it was considered at the forefront of school design when constructed. Through careful stewardship, the Skykomish School building retains its historic integrity both inside and out and has been in continual use serving grades kindergarten through twelve for over 60 years.

Skykomish Library: In November 1944, the town of Skykomish became the first municipality in King County to contact with the King County Library System for library services. For the first 50 years the Library shared the Town Hall building with the Town Office and moved to this building in October of 1993. The building dates from 1947 and has housed several businesses that have come and gone through the years.

Masonic Hall: Still active, the Skykomish Free and Accepter Masons Lodge #259 is the oldest and only surviving fraternal organization in Skykomish. The hall was built in 1924 with donated labor and local materials and through the years has been the hub of many of the town's social events, including the annual Great Northern Days typically held in September.