Downtown Clearwater Brings Artists, Live Music, Fun

To Week 3 of Chalktober Fest from Oct. 15 to 17

Downtown Clearwater will come alive with chalk art artists, live music, shopping, food and drinks and lots of fun this weekend during a special street party on Cleveland Street in Week 3 of Chalktober Fest. Six talented artists will arrive on Thursday, Oct. 15, to begin working on their spectacular chalk art. They plan to complete their creations by noon on Saturday. Oct. 17. Friday night will be the big night, with live music on Cleveland Street.

Chalktober Fest is a month-long celebration of creativity and fun sponsored by the new AMPLIFY Clearwater Chamber of Commerce, serving businesses in Clearwater and Clearwater Beach. The event is presented by Morton Plant Hospital/BayCare Health Systems. (Chalk Art at Morton Plant LEFT)

Four of the artists are sponsored by the Downtown Clearwater Merchants Association on Cleveland Street. Artist Holland King will be located at 522 Cleveland Street between Pour Yours and Soul Fusion. Matt McAllister is scheduled to create his piece at 405 Cleveland Street, east of Capitol Theater’s ticket office, while another artist will be working at 412 Cleveland Street West of Roxy’s. The fourth artist will set up his chalking at 425 Cleveland Street on the south side of the street.

Artist Ashley Whittaker is scheduled to work in front of KnowBe4 at 601 Cleveland Street, while Jenny Pearl will be doing stand-up chalk art, sponsored by Morton Plant Hospital/BayCare during Week 3 of the Experience Clearwater Chalktober Fest Event. Viewers will have an opportunity to vote for their favorites during the Chalktober Fest event.

This is the third week of a five-weekend-long event scheduled at different locations throughout Clearwater Beach and Downtown Clearwater.  Throughout the event, local and visiting artists have been invited to chalk masterpieces in front of a variety of your favorite hot spots in various areas of Downtown Clearwater and Clearwater Beach to attract customers to all participating businesses in a friendly, social distancing way. The participating businesses will be open to offer food and refreshments for those who wish to join in the celebration.

Coming up on Week 4 of Chalktober Fest from October 22-24, the Chalktober Fest art brigade will march to popular Stone Crab weekend on North Clearwater Beach, with Week 5’s final event on the Halloween weekend of October 29-31 in Central Clearwater Beach.

Chalktober Fest is designed to offer residents and visitors an opportunity to see the artists at work and to enjoy viewing their art in a leisurely fashion, while also seeing the reopened businesses that are following all of the post-Pandemic rules while continuing to offer some of the finest quality food and drinks and services that are why Downtown Clearwater and Clearwater Beach are great places to visit.

AMPLIFY Clearwater is the newly combined chambers of commerce from Clearwater and Clearwater Beach. Their stated mission is to promote and meet the needs of businesses, tourism, and industry and to provide leadership for the advancement of economic vitality and equality for the North Pinellas Region. For more information and specific locations of the participating restaurants and businesses, visit www.amplifyclearwater.com/chalktober. Photos courtesy of Amplify Clearwater from the first week’s event of Chalktober Fest.

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