Calle Guanajuato

The IOOF Building in Ashland, Oregon, also known as Oddfellows Building, is a two-story eclectic-styled building in "The Plaza" area of Ashland that was built in 1879. Historically its second story served as a clubhouse of the local International Order of Odd Fellows chapter and the ground floor provided specialty store space. It was listed on the National Register of Historic Places in 1978, for its architecture. From its construction to 1978, the building had served well in the active "Plaza" area of Medford, and continued in its original purposes. Behind the building, by 1978 there was a landscaped park area which had been extended from nearby Lithia Park, where there was once a mill flume.

The Ashland Masonic Lodge Building is a historic building located in Ashland, Oregon. Constructed in 1909 as a meeting hall for a local Masonic lodge, it was listed on the National Register of Historic Places in 1992.It was built in 1880 as a two-story brick building in Italianate to a design by local contractor L.S.P. Marsh. It was expanded in its second floor in 1909 with design by local architect Frank C. Clark, and Clark also designed a third floor added in 1928 along with a remodeling of the building facade into Georgian style. The remodelling added a "a pilaster strip colonnade with stylized Corinthian capitals and full entablature framing the central five bays".With a 50 feet (15 m) frontage, and its superior height of three stories, the building came to "dominate" the block of buildings defining the west side of Ashland's town square.Renovations on the first floor followed a fire in 1959.It was deemed significant for National Register listing in part as its main assembly hall, an upstairs "clear span space 45 feet wide and 55 feet long" with detailed ceiling beams, cornice moldings, pilasters and an encircling entablature, "is one of the few intact lodge rooms of pre-World War I vintage remaining in southern Oregon, and it is replete with historic furniture and equippage."It was included again on the National Register in 2000 as a contributing building in the Ashland Downtown Historic District.

Carter Memorial Fountain is a fountain in Ashland, Oregon, United States. It features Pioneer Mike (or "Iron Mike"), a statue by Allen George Newman. The fountain and statue are part of the Ashland Downtown Historic District, which is listed on the National Register of Historic Places.

The Lithia Fountain is a fountain in Ashland, Oregon, United States, installed in 1927. Health benefits of water from the fountain, and the city's others, have been debated.High barium levels forced the city's public works department to turn off the fountains temporarily in 2016.

The Women's Civic Improvement Clubhouse, at 59 Winburn Way in Ashland, Oregon, was built during 1921–22. Its construction was funded by the Ashland Women's Civic Improvement Club and the philanthropy of Jesse Winburn. It was listed on the National Register of Historic Places in 1989.

The Oregon Shakespeare Festival (OSF) is a regional repertory theatre in Ashland, Oregon, United States, founded in 1935 by Angus L. Bowmer. The Festival now offers matinee and evening performances of a wide range of classic and contemporary plays not limited to Shakespeare. During the Festival, between five and eleven plays are offered in daily rotation six days a week in its three theatres. It welcomed its millionth visitor in 1971, its 10-millionth in 2001, and its 20-millionth visitor in 2015.

The Allen Elizabethan Theatre has evolved since the founding of the Oregon Shakespeare Festival when the first performance of Twelfth Night was presented on July 2, 1935.

Street Scene is a bas-relief sculpture by Marion L. Young installed outside the Chamber of Commerce in Ashland, Oregon, United States. It depicts more than a dozen Shakespearean characters. The artwork was funded by the city's 1988 Downtown Plan, which recommended the installation of fountains and public art in select Ashland locations. Pat Corrigan of the St. Louis Post-Dispatch described the sculpture as "compelling".

MÄS is a Pacific Northwest restaurant in Ashland, Oregon. Chef Josh Dorcak opened the restaurant in 2018.

The Ashland Springs Hotel is a historic hotel in Ashland, Oregon, United States. Built in 1925, it was formerly known as the Mark Antony Motor Hotel or the Lithia Springs Hotel. It was listed on the National Register of Historic Places in 1978 as "Lithia Springs Hotel". It was listed again on the National Register in 2000 as a contributing building in Ashland Downtown Historic District. In 2022 the hotel is also a member of Historic Hotels of America, an official program of the National Trust for Historic Preservation.The Ashland Springs Hotel is a member of Historic Hotels of America, the official program of the National Trust for Historic Preservation. The hotel was built before the Great Depression, originally as the Litha Springs Hotel. It was built as a first-class hotel to draw visitors to the area, designed by the architectural firm Tourtellotte & Hummel with reinforced concrete with architectural elements that reflected a Romanesque, Gothic, and Neo-Classical Revival style. It was planned to be the tallest building between Portland and San Francisco. The design of the hotel was similar to that of the Boise Hotel and the Baker Hotel, featuring a nine-story central tower with two short wings.In 1961, the hotel was renamed to the Mark Antony Motor Hotel. Due to economic issues, the owner undertook an extensive restoration of the hotel under the National Park Service's Certified Rehabilitation program for which the owners received a preservation tax credit.

First Baptist Church is a historic church at 241 Hargadine Street in Ashland, Oregon. It was built in 1911 and added to the National Register in 1979. Ashland's First Baptist Church was sold in the late 1960s. Over the next fifteen years and multiple owners the building remained vacant and deteriorated through vandalism. It was, at one point, painted bright pink, creating a landmark known locally as "the Old Pink Church." In 1982 the boarded-up building was purchased by Craig Hudson to create the Oregon Cabaret Theatre, restoring the structure to its 1911 appearance, including replication of many of the stained glass windows.

The Ashland Downtown Historic District in Ashland, Oregon is a 32.2 acres (13.0 ha) historic district (United States) which was listed on the National Register of Historic Places in 2000. The district is roughly bounded by Lithia Way and C Street, Church, Lithia Park and Hargadine and Gresham Streets. The listing included 55 contributing buildings and six contributing objects, as well as 26 non-contributing buildings and one non-contributing object. Eleven buildings were already separately listed on the National Register. Buildings include: Ashland Masonic Lodge Building, NRHP-listed in 1992 Ashland IOOF Building, or IOOF Building NRHP-listed in 1978 Citizen's Banking & Trust Co. Building, 232-242 E. Main St., NRHP-listed in 1985 Enders Building, 250–300 E. Main St., NRHP-listed in 1986 First Baptist Church (1911), 241 Hargadine Street, NRHP-listed in 1979 First National Bank, NRHP-listed in 1980 Ashland Springs Hotel, also known as the Lithia Springs Hotel and as the Mark Antony Motor Lodge, NRHP-listed in 1978 Fordyce & Julia Roper House, NRHP-listed in 1985 Trinity Episcopal Church, NRHP-listed in 1984 Vaupel Store and Oregon Hotel Building, NRHP-listed in 1980 Whittle Garage Building, NRHP-listed in 1997, and Ashland's City Hall.Contributing objects include: Carter Memorial Fountain