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There are 22 buildings and sites in Sitka that appear in the National Register of Historic Places. On October 18, Alaska celebrates Alaska Day to commemorate the Alaska purchase. The City of Sitka holds an annual Alaska Day Festival. This week-long event includes a reenactment ceremony of the signing of the Alaska purchase, as well as interpretive programs at museums and parks, special exhibits, aircraft displays and film showings, receptions, historic sites and buildings tours, food, prose writing contest essays, Native and other dancing, and entertainment and more. The first recorded Alaska Day Festival was held in 1949.

Sitka hosts one active post-secondary institution, the University of Alaska Southeast-Sitka Campus, located on Japonski Island in an old World War II hangar. Sheldon Jackson College, a small Presbyterian-affiliated private college suspended operations in June, 2007, after several years of financial stress.

Kettleson Memorial Library is the public library for Sitka. It receives about 100,000 guests annually and houses a collection of 75,000 books, audiobooks, music recordings, reference resources, videos (DVD and VHS) as well as an assortment of Alaskan and national periodicals. Its annual circulation is 133,000. The library is well known by visitors for its view. The large windows in front of the reading area look south across Eastern Channel towards the Pyramids. Until its closing, Sitka was also home to Stratton Library, the academic library of Sheldon Jackson College.

Marko Dapcevich, former mayor of Sitka Dale DeArmond, printmaker and book illustrator Annie Furuhjelm, Finnish journalist and legislator Sheldon Jackson, Presbyterian missionary in Alaska in late 19th century Scott McAdams, 2010 Democratic U.S. Senate Candidate Richard Nelson, cultural anthropologist, writer, and activist Teri Rofkar, Tlingit weaver John Straley, award-winning author

Sitka's position between the Pacific Ocean and the most mountainous island in the Alexander Archipelago creates a variety of outdoor opportunities: The Baranof Cross-Island Trail, which leads to the small community of Baranof Warm Springs on the eastern side of the island, is a popular summer backpacking trip. Only serious and experienced backpackers, or those with an experienced guide, should undertake such a trip due to volatile weather conditions in the mountains and the required crossings of icefields with crevasses. The dormant volcano Mount Edgecumbe is also a popular mountain to summit and features a seven-mile (11 km) trail up to the top. Guided day-trips are available, but the trip does not require much knowledge to undertake. The officially unnamed, but informally named Peak 5390 (the name is derived from its height in feet) is the highest point on Baranof Island and a demanding climb. Few people undertake this peak; those interested should consult with one who has summited previously. Kayaking is a popular activity and small guided day excursions are offered locally. There are a number of maintained trails in the Sitka area, many of which are accessible from Sitka's road system.

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