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The Aspen RooftopComedy Festival was a stand-up comedy festival that was held annually in Aspen, Colorado on or around the Memorial Day Weekend since 2008. The festival is the concept of Roxane Davis and the City Of Aspen. Davis, a consultant and producer, created the partnership between rooftopcomedy.com and Aspen's Wheeler Opera House, a historic theater located in downtown Aspen. The Aspen RooftopComedy Festival was designed to fill the gap left by HBO canceling the U.S. Comedy Arts Festival, which had been held in Aspen from 1985 - 2007. HBO has since renamed the festival and relocated it to Las Vegas, Nevada. 2008 marked the inaugural debut of the Aspen Rooftop Comedy Festival as a replacement to the former HBO event. RooftopComedy.com brought the focus of the festival towards an underground talent base and an online media focus, and The Wheeler Opera House ensured that the festival transitioned to an event for the Aspen community by offering affordable tickets and local discounts on festival passes. Whereas the HBO/U.S. Comedy Arts Festival had evolved into primarily an industry event, the producers of the new festival committed to creating a community for developing unproven comics, as well as presenting comedy for a devoted live-comedy audience. The festival ran for three editions, being followed in 2011 by the Aspen Laff Festival.

The former Riede's City Bakery building is located on East Hyman Street in Aspen, Colorado, United States. It is a small wooden commercial building erected in the 1880s. In 1987, it was listed on the National Register of Historic Places. It is one of only two remaining wood frame commercial buildings from the early years of Aspen's development as a silver mining boomtown. It was not originally a bakery, but became known for one that was operated in the building for almost 20 years. Today it is home to a boutique that sells artwork and hand-woven rugs.

The Red Onion is a restaurant located on East Cooper Avenue in Aspen, Colorado, United States. It is the oldest restaurant in the city, housed in a three-story red brick Italianate building dating to the late 19th century. In 1987 it was listed on the National Register of Historic Places as "New Brick–The Brick Saloon", along with other historic properties in the city.It began as a saloon opened by an early city alderman; at one point its upper floors were reportedly home to a brothel. In its early years it was one of three dining establishments in Aspen. It retains much of its original interior, including a bullet hole in the bar. As the city became a popular ski resort, it hosted musical performances by, among others, Billie Holiday and John Denver. It continued operating under various owners for 115 years until closing for structural renovations for three years in the late 2000s.

The Collins Block is a historic commercial building located at 204 South Mill Street in Aspen, Colorado. It is a brick and stone structure erected in the early 1890s. It was the last major construction project in the city before the silver-mining industry, mainstay of Aspen's economy, collapsed following the repeal of the Sherman Silver Purchase Act. The classically inspired decorative touches, such as a colonnade-supported roof over the sidewalk and an elaborate cornice, are the only ones on a commercial building in the city. They anticipate the wider embrace of the Classical Revival style in other cities that began a few years later.For much of its existence it housed a lumber supply store. Local developer Harley Baldwin, owner of the neighboring Brand Building, bought it in 1988. After renovations, he began leasing space within the buildings to upscale retailers, earning the two the combined nickname of "Gucci Gulch". The Caribou Club, a members-only restaurant and Aspen institution, is located in the basement.

The Baldwin Gallery is a contemporary art gallery in Aspen, Colorado established by Richard Edwards in 1994. The gallery features a variety of mainly American but also international contemporary artists and works including painting, drawing, sculpture, photography, video and installation-based work.

The Hyman–Brand Building, often referred to as just the Brand Building, is located at the corner of South Galena Street and East Hopkins Avenue in Aspen, Colorado, United States. It is a two-story stone building erected in the late 19th century. At different stages in the city's history, it was owned by an entrepreneur who used the building in a way that redefined the city for that time. In 1985, it was listed on the National Register of Historic Places. It was built by David Marks Hyman, one of the earliest investors in silver mining during Aspen's early years; it is the only building in Aspen he is known to have financed. Originally home to a bank, it was one of the largest commercial blocks built during the city's boomtown period. Later it was used for several car-related businesses, including a dealership and drive-through gas station in the corner where the bank lobby had once been. In 1971 local entrepreneur Harley Baldwin saved it from demolition, and along with the neighboring Collins Block later renovated it into an area now known as "Glitter Gulch". Today it is home to some upscale boutiques and art galleries.

Aspen City Hall, known in the past as Armory Hall, Fraternal Hall, is located at the intersection of South Galena Street and East Hopkins Avenue in Aspen, Colorado, United States. It is a brick building dating to the 1890s. In 1975 it was listed on the National Register of Historic Places. It was built to serve both as headquarters for the local militia and as a community gathering place. It served a variety of community-related functions, eventually becoming city hall in the mid-20th century. Later in the century, as the city grew again into an affluent resort community, it had to move some of its departments to other office space and renovate the city hall extensively, particularly inside.

The Thomas Hynes House on East Main Street (State Highway 82) in Aspen, Colorado, United States, is a wooden building from the 1880s. In 1987 it was listed on the National Register of Historic Places as part of a group of historic properties in the city. It is one of Aspen's remaining miner's cottages from its early years as a silver boomtown. Since it has never been significantly altered, it is considered one of the best examples remaining. Today it is used as one of Nobu Matsuhisa's eponymous Japanese restaurants.

Aspen Mountain (often called by its former name of Ajax among locals) is a ski area in the western United States, located in Pitkin County, Colorado, just outside and above the city of Aspen. Situated on the north flank of Aspen Mountain (for which it is named), its summit elevation is 11,212 feet (3,417 m) above sea level. Aspen Mountain forms the end of Richmond Ridge, a long ridge that extends ten miles (16 km) south at approximately 11,000 ft (3,350 m) to join the main spine of the Elk Mountains. Founded 78 years ago in 1946 by Walter Paepcke, Aspen was the first ski area venture of the Aspen Skiing Company. It is one of four adjacent ski areas operated by the company as part of the Aspen/Snowmass complex. At only 673 acres (2.7 km2), it is somewhat small compared to other ski areas, especially compared to the much larger nearby Snowmass ski area, and retains a unique cultural flavor that harkens to the earlier days of recreational skiing in the state. The ski area is located within the White River National Forest and is operated under a permit from the U.S. Forest Service. It has three restaurants on the mountain; two are on top (one is a club that only allows members), and one is mid-mountain.

The La Fave Block is located at the intersection of East Cooper Avenue and South Hunter Street in Aspen, Colorado, United States. It is a brick commercial building erected in the late 1880s, during the initial mining boom that created Aspen. Today it is the second oldest brick commercial building in the city, and, along with its neighbors on East Cooper, the only structure left built by Frank LaFave, one of Aspen's early settlers. It was listed on the National Register of Historic Places in 1987. Its ornate Victorian architecture and idiosyncratic fenestration has survived, and it has become one of the most valuable commercial properties in contemporary Aspen due to its location a short distance from the Aspen Mountain ski resort's main lifts. At one point in the 20th century it was the office of an important local architect; and later a ski shop run by Olympic gold medalist Stein Eriksen. Its primary tenant is a clothing store run by Leonard "Boogie" Weinglass, the man said to have inspired a character portrayed by Mickey Rourke. In 2008 it sold for $14.6 million.

The FIS Alpine World Ski Championships 1950 were the 11th FIS Alpine World Ski Championships, held February 13–18 in the United States at Aspen, Colorado.These were the first world championships held outside of Europe, and the first official world championships not concurrent with the Olympics since 1939. The Giant slalom made its world championships debut and displaced the combined event, which returned to the program in 1954 as a "paper race," using the results of the three races (downhill, giant slalom, and slalom) through 1980. At Aspen's Ajax Mountain, Zeno Colò of Italy won the downhill and giant slalom, and just missed a sweep of the gold medals; he finished 0.3 seconds behind in the slalom, taking the silver. Austria dominated the women's races: Dagmar Rom won the giant slalom and slalom, Trude Jochum-Beiser won gold in the downhill and silver in the GS, and Erika Mahringer took two silver medals, in the downhill and slalom. Aspen was in its fourth year as a ski area; it opened in December 1946 with a single chairlift. The Nordic world championships were also held in the U.S. in 1950, at Lake Placid, New York. Due to a lack of snow at Lake Placid, the cross-country events were moved to Rumford, Maine.

The Dixon–Markle House is located at the corner of East Cooper Avenue and South Aspen Street in Aspen, Colorado, United States. It is a wood frame house erected in the 1880s. In 1987 it was listed on the National Register of Historic Places along with other properties in the city. It is believed to have been the house of a successful miner during the silver-mining boom years that established Aspen. A complex application of the Queen Anne architectural style that is unique in the city, it features an unusual projecting bay on its northeast corner. It has remained relatively intact from the time of its construction.