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Community Corner

Your Guide to Tivoli Day in Oak Bluffs

The annual September street festival celebrates the change of seasons with live music, food and shopping galore, plus the excitement of the Ring Challenge at the Flying Horses. What's your favorite part of Tivoli Day? Tell us in the comments.

Written by Mathea Morais and Louisa Hufstader

Saturday marks the 36th year that Circuit Avenue in Oak Bluffs gets blocked off from end to end for an easy-going street fair. Tivoli Day is a day to celebrate all the hard work of the summer and to welcome in the coming of the beautiful Island fall. 

The fun kicks off bright and early with a pancake breakfast from 8 to 10 a.m. at United Methodist Church's Trinity Parish Hall. $8 adults, $5 kids 12 and younger gets a breakfast of pancakes and sausage, scrambled eggs, coffee and juice.

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From 11 a.m. to 6 p.m., Circuit Avenue businesses will open their doors, lining the street with end-of-the-summer sales and outdoor dining from local restaurants. Island musicians including Phil DaRosa and Johnny Hoy and the Bluefish will be playing throughout the day.

At 4:30 p.m., the third annual Jena's Ring Challenge gets underway at the Flying Horses. This fund-raiser supports the Jena Pothier Flying Horses Scholarship Fund, in memory of the 18-year-old victim of a fatal 2009 car crash on the Vineyard.

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Registration for the Ring Challenge, in which riders vie to snatch the most rings as they circle, is $10 for each of four divisions:

  • Mini Junior: 8 and younger
  • Junior: 9 to 15
  • Adult: 16 and older
  • Professional: "Any age, you know who you are."

Will you be going to Tivoli Day this year? What's your favorite part? Tell us in the comments.

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