2005 – “Little Orphant Annie” was the theme for this year’s Festival. Alyssa Brittain reigned over the Festival as Queen. The Ameriana Parade Marshal was Terry Snow who served in Afghanistan. He was also the keynote speaker at the Mayor’s Breakfast.
A new vendor area was established due to the Courthouse renovation. This new area was located behind Greenfield Banking Company in the grassy area between East Street and North State Street.
Singing duo Heart N’ Soul helped open the Festival in the Entertainment Tent. Lindsy Lawyer was the recipient of the James Whitcomb Riley Festival Award.
2006 – The Village Theater on West Main Street was renamed the H.J. Rick’s Theater after it was donated for use as an arts complex. The theater lobby was used for the photography contest when we could no longer use the Courthouse. The Rick’s Theater was also the site for all of the entertainment that had previously been in the Entertainment Tent.
The Riley Festival saw its first injury during the Ameriana Parade. A seven year old boy fell off the float he was riding on and the float then ran over his leg.
The theme for the Festival was “The Jaybird”. David Berard was the President of the Board of Directors. Tickets for the Mayor’s Breakfast were $10.00 each. The keynote speaker was Dr. Larry Baker, a Greenfield native known internationally as a management consultant.
This year also saw a change in the Parade of Flowers. The safety of so many children walking in the parade became a real concern last year, so this year only elementary students in grades 2 – 5 will be in the Parade of Flowers. Next year only students in grade 2 to 4 will be in the parade.
The 2006 Riley Festival Queen was Maggie Leonard. New this year is the Antique Engine and Tractor Show at the 4-H Fairgrounds. This year also saw an old-fashion wedding at the 1840 Encampment. The couple Amanda Davenport and Steve Osborne of Anderson decided this would be the perfect spot for their wedding.
Alisa Huckisson received the Riley Festival Association Community Service Scholarship.
2007 – The theme for the year is “The Mulberry Tree”. Victoria Meyer was crowned the Queen of the 2007 Riley Festival.
Acoustic Catfish was the opening act for the Entertainment Tent on Thursday evening. It was decided that the Festival would go back to using the Entertainment Tent when a deal to rent the Rick’s Theater could not be reached. The temperatures for this year’s Festival broke a record – it was in the 90’s all weekend. The Opening Ceremonies features Anne Hills from Pennsylvania who has set Riley poems to music.
Stephanie Haines was the keynote speaker at the Mayor’s Breakfast. Haines grew up in Greenfield and will share her memories of the Riley Festival. Tickets for the breakfast sold for $10.00. The Fine Art and Photography Contest were held in the Shelter House at the Park.
Terri Stacy a WIBC radio host was the Grand Marshal of the Ameriana Parade. David Berard was President of the Board of Directors and Fred and Debbie Applegate were the General Co-Chairmen of the Festival.
The Riley Festival will no longer be able to use the Courthouse it will be closed for the Festival. New homes will have to be found for the photography or fine art. Amanda Hughes was the winner of the annual James Whitcomb Riley Festival Award.