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Holiday Extravaganza Celebrates the Season with Shopping, Dining, Music, Movies and Fun in Downtown Clearwater

The holiday season is upon us and Downtown Clearwater has plenty of activities, including shopping, boat parade, holiday movies, holiday concerts, dining and more from Nov. 30 through Dec. 22.
Post Date:11/20/2019 2:41 PM

Downtown Clearwater will celebrate the holiday season with its second Holiday Extravaganza that will bring wonderful shopping, dining and events designed for the entire family from Nov. 30 to Dec. 22.

Downtown Clearwater's Cleveland Street will be transformed during the Holiday Extravaganza into a holiday destination with colorful lights, festive decorations, music and activities.

Throughout the Holiday Extravaganza, Downtown Clearwater will offer a unique holiday experience, including specialty shops for holiday shopping, celebrations, tree lighting ceremony, concerts and performances, holiday movies and visits from Santa Claus.

The Holiday Extravaganza events schedule:

  • Nov. 30 – Dec. 22: Holiday Pop-Up Market with unique specialty shops at Second Century Studios, 331 Cleveland St. The shops will be open from 11 a.m. to 7 p.m. Wednesdays through Sundays and will offer an assortment of items for holiday shopping, including jewelry, handmade purses, clothing, body care, cookies, home decor and more. The Pop-Up Market will feature different vendors each week, so visit each week to discover new gift ideas.

  • Nov. 30 and Dec. 1: A food truck rally in Coachman Park and Downtown Clearwater will feature hundreds of food trucks from the region. Hours: Saturday 11 a.m. – 9 p.m., Sunday 11 a.m. – 8 p.m.

  • Dec. 7 from 5 to 10 p.m.: Macy’s presents Miracle on Cleveland Street, a Ruth Eckerd Hall Experience that will include ice skating rink, horse drawn carriage rides, pictures with Santa and Mrs. Claus, live music and the lighting of the Downtown Clearwater holiday tree at 5 p.m. The free festival will take place on the 400-600 blocks of Cleveland Street. Entertainment will include a free concert by The Romantics.

  • Dec. 8 from 4 to 7 p.m.: Annual Santa & Suds 5K Run or Walk and Fun Street Party at 418 Cleveland St. Register at or the day of the race beginning at 2 p.m.

  • Dec. 11, 11:30 a.m. to 1:30 p.m.: A free lunchtime performance by singer Guianna at Station Square Park, 612 Cleveland St.

  • Dec. 12: Get more out of the holidays than just cookies. The Ring, Downtown Clearwater’s newest coworking space focused on wellness, will host several events throughout the day and all throughout downtown focused on wellness, health and creativity.

  • Dec. 13, 5:30 to 9 p.m.: Enjoy a family-friendly night out at the Taste of Downtown Clearwater, featuring local restaurants and merchants, at Station Square Park, 612 Cleveland St., brought to you by the Downtown Clearwater Merchants Association.

  • Dec. 14, 3:30 to 5 p.m.: In a leisurely walk through Downtown Clearwater, see at least 18 unique works of art, from sculptures to murals during the Clearwater Arts Alliance’s Inaugural Public Art Walk. Gather at Second Century Studios, 331 Cleveland St., at 3:30 p.m. to meet and shop the Holiday Pop-Up Market. The docent-led tour begins promptly at 4 p.m. and will last approximately one hour within a six block radius. Free event.

  • Dec. 14 at 6 p.m.: A Holiday Movie Night with the delightful Christmas movie “Elf” at Station Square Park, 612 Cleveland St. The movie will feature a special guest, the one and only Santa Claus, who will host a meet and greet with the children. Holiday treats and snacks will be available. Free event.

  • Dec. 14 at 8 to 10 p.m.: Island Estates Holiday Boat Parade. Get a great seat at Coachman Park, 301 Drew St., as decorated boats light up the night and add to the holiday festivities. The Florida Brass Alumni Drum and Bugle Corps Holiday Concert will take place before the parade at 7 p.m.

  • Dec. 21 at 6 p.m.: Holiday Movie Night with “The Grinch” (2018) at Station Square Park, 612 Cleveland St. There will be a free live musical performance by the James Suggs Jazz Quartet at 6 p.m. followed by the movie. The movie night will also feature a special guest, the one and only Santa Claus, who will host a meet and greet with children. Holiday treats and snacks will be available. Free event.

    Second Century Studios will also host arts and crafting events throughout the month, including holiday ornament painting, wreath-making, drawing classes and photography seminars, starting Dec. 6. Visit for details on this year’s Holiday Extravaganza!

    Park for free all day on weekends and after 6 p.m. on weekdays at city parking garages and on-street parking. For parking information, visit or call (727) 562-4704 from 8:30 a.m. to 5 p.m. Monday through Friday.

    The Holiday Extravaganza is sponsored by the city of Clearwater’s Community Redevelopment Agency, and in part by the Downtown Development Board and The Ring.

    The City of Clearwater Community Redevelopment Agency

    The City of Clearwater’s Community Redevelopment Agency aims to promote Downtown Clearwater’s ongoing neighborhood revitalization through programs and initiatives that strengthen and stimulate our local economy and community. For more information, visit

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