Mickelson-Chapman Fountain

Trinity Episcopal Church is a historic Episcopal church at 44 N. 2nd Street in Ashland, Oregon. It is also the oldest church in Ashland. Constructed in 1894 and completed in 1895, its design was based on drawings by local builder W. J. Schmidt. Built in the Gothic Revival style, it features a pitched gable roof, a pointed west-facing window, a gabled south-facing porch, and a trussed rafter roof. The church was added to the National Register of Historic Places in 1984. It was included again on the National Register in 2000 as a contributing building in the Ashland Downtown Historic District.

Smithfields refers to two related businesses in Ashland, Oregon, United States: Smithfields Restaurant and Bar and Smithfields Pub and Pies.

The Columbia Hotel is a former European-style hotel in Ashland, Oregon, and at the time of its closing in 2021 had been in continuous operation since its construction in 1910. The hotel occupied the second floor of the Enders Building, listed on the National Register of Historic Places in 1986.Designed by architect Frank Chamberlain Clark, the Enders Building was the first concrete commercial structure in Ashland. The Ashland Tidings, December 12, 1910, called it "the largest structure of its kind in Southern Oregon." Featuring characteristics of the Chicago style, it is also significant as an early example of a department store. Hotel accommodations on the second level were constructed to make it possible for shoppers from Northern California as well as from Oregon towns as far north as Grants Pass to travel to the mercantile shops in downtown Ashland by wagon, train, or car to shop and then stay the night at the hotel, and return home the next day.For decades, under the direction of local businessman H.G. Enders, the building was the largest mercantile establishment between Sacramento and Portland. The Columbia Hotel, the only surviving Ashland hotel from this period, remained true to its original construction with much of the original fixtures, furniture, and all of the original millwork. Its interior featured an antique tin-lined wooden telephone booth, believed to be the oldest booth in Oregon still serving callers.The same year the Enders Building brought its shops, restaurant, and Columbia Hotel to Ashland the Citizens Banking and Trust Co. Building went up next door (with a bank, grocery, and professional offices), while a four-story Elks Lodge (BPOE #944) was constructed directly across the street—all part of the 1909–1913 building boom that shifted attention and commerce away from Ashland's traditional town center, the Plaza. On October 10, 2010, Ashland temporarily closed a stretch of Main Street for a centennial celebration in which re-dedication ceremonies were held at both the Columbia Hotel and Elks Lodge.The Columbia Hotel closed permanently on November 1, 2021, after 111 years in operation, the longest of any continuously operating hotel in Oregon.

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

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 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.

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

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".

The Ashland Oregon National Guard Armory aka "The Historic Ashland Armory" is an armory building located in the historic district of Ashland, Oregon, in the United States. It was designed by William C. Knighton, Oregon's first State Architect, and was built from 1912 to 1913. The armory displays California Mission and Gothic Revival architectural styles and remains one of four pre-World War I armories in western Oregon. It is listed on the National Register of Historic Places.It has been a cultural center, event space and music venue for the local community since the 1950's. It is also a commercial office space with over 25 office rentals.

The Nils Ahlstrom House is a nineteenth century Classical Revival house located in Ashland, Oregon. Built in 1888 by Nils Ahlstrom, a railroad worker who had emigrated from Sweden, the home was listed on the National Register of Historic Places in 1980.

Ashland Cemetery is a cemetery in Ashland, Oregon, in the United States. It is listed on the National Register of Historic Places. Notable burials include Lindsay Applegate and Abel Helman.

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.