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They can earn hundreds of dollars to save others a spot in line at sample sales, trendy restaurants and more.
She had a 37-year run at Mother McAuley Liberal Arts High School in Mount Greenwood, where she led the theater program, eventually going on to create the 99th Street Summer Theatre Festival, a children's summer camp and other programming.
They told us about Old Town's history, Beverly's hills, South Shore's big city feel and small town energy.
Some small business owners said they plan to close during the two-day event, but others are excited about the race and the boost in pedestrian traffic that could bring more sales.