Mainsail Art Festival started in 1976 when the city's Bicentennial Committee, the Saint Petersburg Recreation Department and the new Saint Petersburg Arts Commission joined forces to sponsor the "First Annual Saint Petersburg Sidewalk Arts and Colonial Crafts Festival." For the second show, the name was shortened. "Mainsail" was chosen in 1977 to convey the event's importance, its excitement and marina setting in waterfront South Straub Park. For several years, a huge sail was hoisted prominently in the park as the festival's trademark logo, provided by a local yacht corporation.
In the Spring of 1988, the show moved to a larger location in North Straub Park, just one block north of the original spot, to accommodate needs for a larger entertainment tent, children's activity area, demonstration area and food vendors. In 2004, the show was moved to Vinoy Park to accommodate more artists.
Originally, first and second place awards were given out in each category. In recent years, awards of excellence, distinction and merit are given at the 2008 Judge's discretion without regard to category. Early records indicate the festival offered less than $4,200 in cash prizes the first five years; which increased to $9,000 by 1982; $13,500 in 1986; and as of 2006 cash awards total $50,000.
Mainsail's nautical theme saw the addition of the bright pink flamingo design in 1986, which is now a tradition on festival letterhead and park signage. The sailboat trademark from the origin of the festival is still used for souvenir merchandise and the annual commemorative poster.
Various additions have developed into traditions over the past 31 years, such as: The Awards Ceremony and Saturday evening barbecue in the park added in 1978 to accommodate artists. In 2005, the Saturday evening affair was replaced with a Sunday Morning Breakfast and Awards Ceremony. Catering to the participating artists was a priority from the start. Another traditional perk for the exhibiting artist was established approximately in 1985: a "Purchase Award" consists of the purchase of selected pieces of art by up to a dozen corporate sponsors. In addition to their artwork being selected, the artist receives a ribbon award and extra $200.
Entertainment now consists of mostly local talent which has a large local and regional drawing featuring R&B, Jazz, Country, Big Band, etc. Occasionally, a known national entertainer may perform which adds to a fun filled weekend of quality visual and performing arts.
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