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X-ORIGINAL-URL:https://www.positivelyosceola.com
X-WR-CALDESC:Events for Positively Osceola
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DTSTART;TZID=America/New_York:20260325T170000
DTEND;TZID=America/New_York:20260325T210000
DTSTAMP:20260501T080254
CREATED:20260310T203847Z
LAST-MODIFIED:20260310T203847Z
UID:10005560-1774458000-1774472400@www.positivelyosceola.com
SUMMARY:Downtown Saint Cloud Monthly Market
DESCRIPTION:A monthly evening market in Historic Downtown St. Cloud offers a community gathering where local makers and bakers showcase their goods in a festive outdoor setting. String lights illuminate the area as music fills the air\, creating a lively atmosphere designed to bring residents and visitors together. \nThe market is hosted on the last Wednesday of each month\, with the spring season running from January through April. \nOrganizers note that road closures will be in effect during the event\, and visitors are encouraged to plan accordingly. \nMarkets will be held rain or shine\, though adjustments may be made in the event of extreme weather. Any updates will be shared with the public. \nVendor applications for the current season are closed. Those with questions may contact organizers at downtownmonthlymarket@gmail.com. Applications for the fall market season are expected to open around July and will be announced on the event’s social media pages.
URL:https://www.positivelyosceola.com/event/downtown-saint-cloud-monthly-market-2/
LOCATION:Downtown St. Cloud\, New York Avenue\, St. Cloud\, Florida\, 34769
ATTACH;FMTTYPE=image/jpeg:https://www.positivelyosceola.com/wp-content/uploads/2026/03/644503965_940418118672609_1765005730534612670_n.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20260314T170000
DTEND;TZID=America/New_York:20260314T230000
DTSTAMP:20260501T080254
CREATED:20260201T004548Z
LAST-MODIFIED:20260201T004548Z
UID:10005514-1773507600-1773529200@www.positivelyosceola.com
SUMMARY:St. Patrick's Paint the Cloud Green
DESCRIPTION:Let’s Paint The Cloud Green for St. Patrick’s Day! Join us downtown on Saturday\, March 14\, from 5 p.m. to 11 p.m. This year\, we’ll have a 5K glow run\, a St. Baldrick’s head-shaving fundraiser for children’s cancer\, activities for the kids\, live Irish music from Murphy’s Law\, and the return of Food Truck Wars!\nIt’s fun for the whole family\, and you won’t want to miss it!\nPaint the Cloud Green is sponsored by the City of St. Cloud\, AdventHealth\, Experience Kissimmee\, Toho Water Authority\, Willpower Athletics\, and Confessions of the Hand Tattoo and Fine Art Gallery.\n5K Glow Run Registration: https://runsignup.com/Race/Register?raceId=171246\nSt. Baldrick’s Children’s Cancer Fundraiser: https://www.stbaldricks.org/events/shavefest2026
URL:https://www.positivelyosceola.com/event/st-patricks-paint-the-cloud-green/
LOCATION:Downtown St. Cloud\, New York Avenue\, St. Cloud\, Florida\, 34769
CATEGORIES:City of St. Cloud
ATTACH;FMTTYPE=image/png:https://www.positivelyosceola.com/wp-content/uploads/2026/01/Screenshot-2026-01-31-at-7.41.02-PM.png
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20260228T100000
DTEND;TZID=America/New_York:20260228T160000
DTSTAMP:20260501T080254
CREATED:20260114T024037Z
LAST-MODIFIED:20260114T024037Z
UID:10005465-1772272800-1772294400@www.positivelyosceola.com
SUMMARY:Roots & Rhythm Festival
DESCRIPTION:St. Cloud Main Street and Granny’s Southern Smokehouse present the Roots & Rhythm Festival on February 28th\, taking place in Downtown St. Cloud from 10 a.m.–4 p.m. This vibrant community celebration honors history\, culture\, and creativity through music\, food\, art\, and local entrepreneurship. \nJoin us as we celebrate through soulful performances\, flavorful cuisine\, and local vendors — a space to connect\, uplift\, and enjoy the rich cultural experiences our wider community has to offer. \n\nRoots & Rhythm Festival is now accepting vendors and food trucks!\n\n\nWe’re excited to start building this year’s lineup of makers\, small businesses\, artisans\, and food vendors. If you want to be part of a community focused event that celebrates culture\, creativity\, and connection\, we’d love to have you join us.\n\n\nVendor and food truck applications are now live on our website — spots will fill up\, so don’t wait!\n\n\nApply today and be part of Roots & Rhythm Festival: https://stcloudmainstreet.org/roots-and-rhythm-festival/
URL:https://www.positivelyosceola.com/event/roots-rhythm-festival/
LOCATION:Downtown St. Cloud\, New York Avenue\, St. Cloud\, Florida\, 34769
CATEGORIES:St. Cloud Main Street
ATTACH;FMTTYPE=image/png:https://www.positivelyosceola.com/wp-content/uploads/2026/01/Screenshot-2026-01-13-at-9.35.41-PM-scaled.png
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20260225T173000
DTEND;TZID=America/New_York:20260225T200000
DTSTAMP:20260501T080254
CREATED:20260205T031036Z
LAST-MODIFIED:20260205T031036Z
UID:10005522-1772040600-1772049600@www.positivelyosceola.com
SUMMARY:Historic Walking and Ghost Tours
DESCRIPTION:Stories. Spirits. Streets.\n\n\nThe Historic Walking & Ghost Tours continues on February 25—step into the next spine-tingling experience of the season.\n\n\nWander through historic downtown\nUncover chilling legends and haunted lore\n\n\n5:30 PM – Historic Walking Tour: https://www.zeffy.com/…/ticketing/historic-walking-tours-2\n8:00 PM – Historic Ghost Tour: https://www.zeffy.com/en-US/ticketing/historic-ghost-tour-2\n\n\nTickets are limited and now available on our new ticketing platform—reserve your spot today!
URL:https://www.positivelyosceola.com/event/historic-walking-and-ghost-tours-2/
LOCATION:Downtown St. Cloud\, New York Avenue\, St. Cloud\, Florida\, 34769
CATEGORIES:St. Cloud Main Street
ATTACH;FMTTYPE=image/png:https://www.positivelyosceola.com/wp-content/uploads/2026/02/Screenshot-2026-02-04-at-9.49.45-PM.png
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20260225T173000
DTEND;TZID=America/New_York:20260225T200000
DTSTAMP:20260501T080254
CREATED:20260205T025410Z
LAST-MODIFIED:20260205T025410Z
UID:10005521-1772040600-1772049600@www.positivelyosceola.com
SUMMARY:Historic Walking and Ghost Tours
DESCRIPTION:Stories. Spirits. Streets.\n\n\nThe Historic Walking & Ghost Tours continues on February 25—step into the next spine-tingling experience of the season.\n\n\nWander through historic downtown\nUncover chilling legends and haunted lore\n\n\n5:30 p.m. – Historic Walking Tour: https://www.zeffy.com/…/ticketing/historic-walking-tours-2\n8:00 p.m. – Historic Ghost Tour: https://www.zeffy.com/en-US/ticketing/historic-ghost-tour-2\n\n\nTickets are limited and now available on our new ticketing platform—reserve your spot today!
URL:https://www.positivelyosceola.com/event/historic-walking-and-ghost-tours/
LOCATION:Downtown St. Cloud\, New York Avenue\, St. Cloud\, Florida\, 34769
CATEGORIES:St. Cloud Main Street
ATTACH;FMTTYPE=image/png:https://www.positivelyosceola.com/wp-content/uploads/2026/02/Screenshot-2026-02-04-at-9.49.45-PM.png
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20260201T100000
DTEND;TZID=America/New_York:20260201T180000
DTSTAMP:20260501T080254
CREATED:20260122T191912Z
LAST-MODIFIED:20260122T191912Z
UID:10005486-1769940000-1769968800@www.positivelyosceola.com
SUMMARY:Rayzor's Edge Music and Bike Fest
DESCRIPTION:17th Annual Cancer Awareness Event\n\n\nJoin us for a powerful day of Food\, Fun\, Music\, and Military History as our 17th Annual Cancer Awareness Event proudly teams up with Chris Robertson\, Mayor of St. Cloud\, and the Museum of Military History.\n\n\nThis one-of-a-kind event brings the community together to honor strength\, remembrance\, and resilience—while celebrating our military history in an unforgettable setting. Families\, vendors\, supporters\, and history lovers are all welcome.\n\n\nLive music\nGreat food\nMilitary history displays\nA cause that truly matters\n\n\nSpots are filling up fast\, sign up today and be part of a meaningful tradition that’s been making an impact for 17 years.\n\n\nUse Coupon Code: Awareness20 to save $20 today!\n\n\nBe part of the cause. Be part of history.
URL:https://www.positivelyosceola.com/event/rayzors-edge-music-and-bike-fest/
LOCATION:Downtown St. Cloud\, New York Avenue\, St. Cloud\, Florida\, 34769
CATEGORIES:Downtown St. Cloud
ATTACH;FMTTYPE=image/png:https://www.positivelyosceola.com/wp-content/uploads/2026/01/Screenshot-2026-01-22-at-2.15.50-PM-scaled.png
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20260128T170000
DTEND;TZID=America/New_York:20260128T210000
DTSTAMP:20260501T080254
CREATED:20260122T191214Z
LAST-MODIFIED:20260122T191214Z
UID:10005484-1769619600-1769634000@www.positivelyosceola.com
SUMMARY:St. Cloud Downtown Monthly Market
DESCRIPTION:A magical evening market where makers & bakers shine bright. String lights twinkle overhead as music fills the air. This isn’t just any market – it’s a community celebration.\nHosted the last Wednesday of the month\, the spring market season runs January-April. Located in Historic Downtown St Cloud. This event does include road closures so please plan accordingly. Markets are rain or shine. Adjustments will be made due to any extreme weather and updates shared.\nVendors can sign up using application link on our page. Please do not contact anyone directly commenting claiming to have vendor availability.
URL:https://www.positivelyosceola.com/event/st-cloud-downtown-monthly-market/
LOCATION:Downtown St. Cloud\, New York Avenue\, St. Cloud\, Florida\, 34769
CATEGORIES:Downtown St. Cloud
ATTACH;FMTTYPE=image/png:https://www.positivelyosceola.com/wp-content/uploads/2026/01/Screenshot-2026-01-22-at-2.09.14-PM.png
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20260117T100000
DTEND;TZID=America/New_York:20260117T100000
DTSTAMP:20260501T080254
CREATED:20260114T201627Z
LAST-MODIFIED:20260114T201627Z
UID:10005467-1768644000-1768644000@www.positivelyosceola.com
SUMMARY:Sidewalk Sales - Downtown St. Cloud
DESCRIPTION:Shop retail shops end of season sale and clearance items. Find sales racks outside and inside businesses throughout the historic downtown. Enjoy cafes & eateries while you’re shopping.
URL:https://www.positivelyosceola.com/event/sidewalk-sales-downtown-st-cloud/
LOCATION:Downtown St. Cloud\, New York Avenue\, St. Cloud\, Florida\, 34769
CATEGORIES:Downtown St. Cloud
ATTACH;FMTTYPE=image/png:https://www.positivelyosceola.com/wp-content/uploads/2026/01/Screenshot-2026-01-14-at-3.14.03-PM.png
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20260117T090000
DTEND;TZID=America/New_York:20260117T090000
DTSTAMP:20260501T080254
CREATED:20251111T175944Z
LAST-MODIFIED:20251111T175944Z
UID:10004622-1768640400-1768640400@www.positivelyosceola.com
SUMMARY:Walking tour of St. Cloud downtown murals
DESCRIPTION:Join us for a walking tour of the downtown St. Cloud murals\, starting at 1012 Massachusetts Ave. Purchase tickets at the St. Cloud Heritage Museum Thursday\, Friday\, or Saturday 11 a.m.-3 p.m. For more information\, call Cede Hofmann  at 407-873-2930.
URL:https://www.positivelyosceola.com/event/walking-tour-of-st-cloud-downtown-murals/
LOCATION:Downtown St. Cloud\, New York Avenue\, St. Cloud\, Florida\, 34769
CATEGORIES:St Cloud Woman's Club
ATTACH;FMTTYPE=image/png:https://www.positivelyosceola.com/wp-content/uploads/2025/11/Screenshot-2025-11-11-at-12.49.24-PM.png
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20251231T190000
DTEND;TZID=America/New_York:20260101T010000
DTSTAMP:20260501T080254
CREATED:20251124T022500Z
LAST-MODIFIED:20251124T022500Z
UID:10004915-1767207600-1767229200@www.positivelyosceola.com
SUMMARY:Rockin' the Cloud - New Year's Eve
DESCRIPTION:St. Cloud’s biggest New Year’s Eve celebration returns. Rockin’ the Cloud takes place Wednesday\, December 31\, from 7 p.m. to 1 a.m. in Historic Downtown St. Cloud.\n\n\nWe are excited to welcome Less Than Jake as this year’s main stage headliner!\n\n\nEnjoy free general admission or elevate your night with our $75 Cloud VIP experience\, which includes gourmet hors d’oeuvres\, private restrooms\, VIP viewing area\, and more.\n\n\n\nCall 407-957-7243 for VIP information.
URL:https://www.positivelyosceola.com/event/rockin-the-cloud-new-years-eve/
LOCATION:Downtown St. Cloud\, New York Avenue\, St. Cloud\, Florida\, 34769
CATEGORIES:City of St. Cloud
ATTACH;FMTTYPE=image/png:https://www.positivelyosceola.com/wp-content/uploads/2025/11/Screenshot-2025-11-23-at-9.19.13-PM.png
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20251220T140000
DTEND;TZID=America/New_York:20251220T190000
DTSTAMP:20260501T080254
CREATED:20251118T174428Z
LAST-MODIFIED:20251118T174428Z
UID:10004626-1766239200-1766257200@www.positivelyosceola.com
SUMMARY:Ugly Sweater Wine Walk in the Cloud
DESCRIPTION:Grab your friends and your ugliest Christmas sweater for December’s wine walk in the Cloud! Get your tickets on the Eventbrite link below. Returning wine walkers buy your tix on site and bring your reusable plastic glass back with you to save five dollars off! \nhttps://www.eventbrite.com/e/wine-walk-in-the-cloud-tickets-1076743742519?aff=erelpanelorg
URL:https://www.positivelyosceola.com/event/ugly-sweater-wine-walk-in-the-cloud/
LOCATION:Downtown St. Cloud\, New York Avenue\, St. Cloud\, Florida\, 34769
CATEGORIES:Downtown St. Cloud
ATTACH;FMTTYPE=image/png:https://www.positivelyosceola.com/wp-content/uploads/2025/11/Screenshot-2025-11-18-at-12.38.06-PM.png
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20251212T180000
DTEND;TZID=America/New_York:20251212T210000
DTSTAMP:20260501T080254
CREATED:20251202T015723Z
LAST-MODIFIED:20251202T015723Z
UID:10004987-1765562400-1765573200@www.positivelyosceola.com
SUMMARY:Christmas Pajama Party
DESCRIPTION:Break out your favorite festive pj’s and come for a fun shopping night in Downtown St Cloud!\nEnjoy a night of festive lights\, hot cocoa and holiday shopping. Sip some evening cocktails\, grab a bite to eat and don’t skip dessert!
URL:https://www.positivelyosceola.com/event/christmas-pajama-party/
LOCATION:Downtown St. Cloud\, New York Avenue\, St. Cloud\, Florida\, 34769
CATEGORIES:Downtown St. Cloud
ATTACH;FMTTYPE=image/png:https://www.positivelyosceola.com/wp-content/uploads/2025/12/Screenshot-2025-12-01-at-8.55.02-PM.png
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20251207T090000
DTEND;TZID=America/New_York:20251207T170000
DTSTAMP:20260501T080254
CREATED:20251124T190311Z
LAST-MODIFIED:20251124T190311Z
UID:10004918-1765098000-1765126800@www.positivelyosceola.com
SUMMARY:St. Cloud Holiday Festival
DESCRIPTION:Get ready for a full day of festive fun in the heart of St. Cloud! This year’s Holiday Festival brings together local crafters and artists\, live performances\, an exciting Kids Zone the whole family will love\, fabulous food trucks\, and MUCH more. Don’t miss your chance to grab photos with Santa\, enjoy delicious festival food\, and explore amazing local dining and shopping options throughout the area.\nBring the family and kick off the season with community cheer!
URL:https://www.positivelyosceola.com/event/st-cloud-holiday-festival-2/2025-12-07/
LOCATION:Downtown St. Cloud\, New York Avenue\, St. Cloud\, Florida\, 34769
CATEGORIES:City of St. Cloud
ATTACH;FMTTYPE=image/png:https://www.positivelyosceola.com/wp-content/uploads/2025/11/Screenshot-2025-11-24-at-1.57.52-PM.png
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20251206T100000
DTEND;TZID=America/New_York:20251206T120000
DTSTAMP:20260501T080254
CREATED:20251018T002827Z
LAST-MODIFIED:20251018T002827Z
UID:10001969-1765015200-1765022400@www.positivelyosceola.com
SUMMARY:2025 St. Cloud Christmas Parade presented by Orlando Health - St. Cloud Hospital
DESCRIPTION:The Annual Christmas parade\, presented by Orlando Health St. Cloud Hospital and the City of Saint Cloud\, is brought to you by Experience Kissimmee.\nThis year’s theme for the Christmas parade is “The Magic of Christmas.”\nThe St. Cloud Christmas parade is a family-friendly event\, featuring festivities for all ages. This locally televised event will also be live-streamed on the St. Cloud Chamber’s social media pages.\nCome down to downtown St. Cloud to enjoy the parade\, and make sure to stay for the craft show! Check out our newly remodeled Santa Sleigh and see the businesses in the community that are making a positive impact. We look forward to seeing you all there!
URL:https://www.positivelyosceola.com/event/2025-st-cloud-christmas-parade-presented-by-orlando-health-st-cloud-hospital/
LOCATION:Downtown St. Cloud\, New York Avenue\, St. Cloud\, Florida\, 34769
CATEGORIES:City of St. Cloud
ATTACH;FMTTYPE=image/png:https://www.positivelyosceola.com/wp-content/uploads/2025/10/Untitled-design-4-scaled.png
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20251206T090000
DTEND;TZID=America/New_York:20251206T170000
DTSTAMP:20260501T080254
CREATED:20251124T190311Z
LAST-MODIFIED:20251124T190311Z
UID:10004917-1765011600-1765040400@www.positivelyosceola.com
SUMMARY:St. Cloud Holiday Festival
DESCRIPTION:Get ready for a full day of festive fun in the heart of St. Cloud! This year’s Holiday Festival brings together local crafters and artists\, live performances\, an exciting Kids Zone the whole family will love\, fabulous food trucks\, and MUCH more. Don’t miss your chance to grab photos with Santa\, enjoy delicious festival food\, and explore amazing local dining and shopping options throughout the area.\nBring the family and kick off the season with community cheer!
URL:https://www.positivelyosceola.com/event/st-cloud-holiday-festival-2/2025-12-06/
LOCATION:Downtown St. Cloud\, New York Avenue\, St. Cloud\, Florida\, 34769
CATEGORIES:City of St. Cloud
ATTACH;FMTTYPE=image/png:https://www.positivelyosceola.com/wp-content/uploads/2025/11/Screenshot-2025-11-24-at-1.57.52-PM.png
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20251205T000000
DTEND;TZID=America/New_York:20251220T000000
DTSTAMP:20260501T080254
CREATED:20251202T015150Z
LAST-MODIFIED:20251202T015150Z
UID:10004986-1764892800-1766188800@www.positivelyosceola.com
SUMMARY:St. Cloud 2025 Holiday Events
DESCRIPTION:Downtown St Cloud is full of festivities this holiday season.\n\n\n\nShop\, dine & enjoy the downtown community this season. We hope this little list of dates helps in the busy season and stay tuned as we continue to post more about specific upcoming events.
URL:https://www.positivelyosceola.com/event/st-cloud-2025-holiday-events/
LOCATION:Downtown St. Cloud\, New York Avenue\, St. Cloud\, Florida\, 34769
ATTACH;FMTTYPE=image/png:https://www.positivelyosceola.com/wp-content/uploads/2025/12/Screenshot-2025-12-01-at-8.45.21-PM-1.png
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20251129T090000
DTEND;TZID=America/New_York:20251129T090000
DTSTAMP:20260501T080254
CREATED:20251118T173723Z
LAST-MODIFIED:20251118T173723Z
UID:10004625-1764406800-1764406800@www.positivelyosceola.com
SUMMARY:Small Business Saturday
DESCRIPTION:Small Business Saturday is coming up on November 29\, 2025!This day is all about showing love to the independent shops\, makers\, and local favorites that give our community its character. When you shop small\, you’re not just buying a product—you’re helping local owners thrive\, supporting local jobs\, and keeping money circulating right here at home.\nSo take a stroll downtown\, explore the unique spots you’ve been meaning to visit\, and make a day out of supporting the businesses that make our community special.
URL:https://www.positivelyosceola.com/event/small-business-saturday-2/
LOCATION:Downtown St. Cloud\, New York Avenue\, St. Cloud\, Florida\, 34769
CATEGORIES:Downtown St. Cloud
ATTACH;FMTTYPE=image/png:https://www.positivelyosceola.com/wp-content/uploads/2025/11/Screenshot-2025-11-18-at-12.35.11-PM.png
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20251119T170000
DTEND;TZID=America/New_York:20251119T210000
DTSTAMP:20260501T080254
CREATED:20251110T233216Z
LAST-MODIFIED:20251110T233216Z
UID:10004615-1763571600-1763586000@www.positivelyosceola.com
SUMMARY:Downtown Monthly Market
DESCRIPTION:A magical evening market where makers & bakers shine bright. String lights twinkle overhead as music fills the air. This isn’t just any market – it’s a community celebration.\nHosted the last Wednesday of the month\, the fall market season runs September-December. This event does include road closures so please plan accordingly. Markets are rain or shine. Adjustments will be made due to any holidays\, extreme weather and updates shared.\nVendor applications are currently closed. Please email downtownmonthlymarket@gmail.com for more information about our waiting list.
URL:https://www.positivelyosceola.com/event/downtown-monthly-market-3/
LOCATION:Downtown St. Cloud\, New York Avenue\, St. Cloud\, Florida\, 34769
CATEGORIES:Downtown St. Cloud
ATTACH;FMTTYPE=image/png:https://www.positivelyosceola.com/wp-content/uploads/2025/11/Screenshot-2025-11-10-at-6.26.05-PM.png
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20251031T170000
DTEND;TZID=America/New_York:20251031T230000
DTSTAMP:20260501T080254
CREATED:20251024T132506Z
LAST-MODIFIED:20251024T132506Z
UID:10004565-1761930000-1761951600@www.positivelyosceola.com
SUMMARY:Witches & Maniacs: Trick or Treating\, Block Party\, Car Show
DESCRIPTION:Join St. Cloud Main Street for a fang-tastic time this Halloween! On Friday\, October 31\, our historic downtown will transform into a eerie-sistible celebration you won’t want to miss. From 5 p.m. – 8 p.m.\, little ghouls and goblins can trick-or-treat at local businesses for a cauldron of sweet surprises. From 6 p.m. – 9 p.m.\, don’t miss the spook-tacular Car Show. From 8 p.m. – 11 p.m.\, enjoy music that will raise your spirits\, wickedly fun games\, and dancing that’ll make you boo-gie all night long. Don’t miss the hair-raising costume contest — show off your howl-oween best outfit for a chance to win!\n\nFor more information: https://stcloudmainstreet.org/witches-maniacs-halloween…/
URL:https://www.positivelyosceola.com/event/witches-maniacs-trick-or-treating-block-party-car-show/
LOCATION:Downtown St. Cloud\, New York Avenue\, St. Cloud\, Florida\, 34769
CATEGORIES:St. Cloud Main Street
ATTACH;FMTTYPE=image/png:https://www.positivelyosceola.com/wp-content/uploads/2025/10/Untitled-design-20.png
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20251029T170000
DTEND;TZID=America/New_York:20251029T210000
DTSTAMP:20260501T080254
CREATED:20251018T021738Z
LAST-MODIFIED:20251018T021738Z
UID:10001970-1761757200-1761771600@www.positivelyosceola.com
SUMMARY:St. Cloud Monthly Market
DESCRIPTION:A magical evening market where makers & bakers shine bright. String lights twinkle overhead as music fills the air. This isn’t just any market – it’s a community celebration.\nHosted the last Wednesday of the month\, the fall market season runs September-December. This event does include road closures so please plan accordingly. Markets are rain or shine. Adjustments will be made due to any extreme weather and updates shared.\nVendor applications are currently closed. Please email downtownmonthlymarket@gmail.com for more information about our waiting list.
URL:https://www.positivelyosceola.com/event/st-cloud-monthly-market/
LOCATION:Downtown St. Cloud\, New York Avenue\, St. Cloud\, Florida\, 34769
CATEGORIES:City of St. Cloud
ATTACH;FMTTYPE=image/png:https://www.positivelyosceola.com/wp-content/uploads/2025/10/Untitled-design-5-scaled.png
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20250323T100000
DTEND;TZID=America/New_York:20250323T173000
DTSTAMP:20260501T080254
CREATED:20250113T012923Z
LAST-MODIFIED:20250113T012923Z
UID:10001914-1742724000-1742751000@www.positivelyosceola.com
SUMMARY:Rayzor Edge Music Festival
DESCRIPTION:Enjoy music\, food vendors\, drinks\, and craft vendors. All proceeds go to relay for life.
URL:https://www.positivelyosceola.com/event/rayzor-edge-music-festival/
LOCATION:Downtown St. Cloud\, New York Avenue\, St. Cloud\, Florida\, 34769
CATEGORIES:City of St. Cloud
ATTACH;FMTTYPE=image/jpeg:https://www.positivelyosceola.com/wp-content/uploads/2025/01/Rayzor-Edge-Music-Festival.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20250215T100000
DTEND;TZID=America/New_York:20250215T120000
DTSTAMP:20260501T080254
CREATED:20250120T023448Z
LAST-MODIFIED:20250120T023448Z
UID:10001919-1739613600-1739620800@www.positivelyosceola.com
SUMMARY:Silver Spurs Rodeo Parade
DESCRIPTION:Start a new tradition and be a part of a cherished event\, the Silver Spurs Rodeo Parade! On February 15 at 10:00 a.m.\, the Silver Spurs Rodeo Parade will take place in Downtown St. Cloud\, starting at Pennsylvania and Lakeshore. This local event is free and open to the public\, so come together and experience the heart and soul of Osceola County with real cowboys\, charming local culture\, and a whole lot of fun. \nBring your family and friends to celebrate the kickoff of rodeo season with rodeo queens\, the Silver Spurs Quadrille\, fire trucks\, demonstrations of popping whips and roping\, local elected officials\, and honored Silver Spurs Riding Club members. Everyone is welcome! \nWant to be a part of the parade? This year’s theme is “Ride Your Brand\,” and our organization encourages all businesses to join in on the fun. There’s also an exciting prize for the best-designed floats! Sign up here: https://www.silverspursrodeo.com/silver-spurs-parade… \nCome and be part of this unique celebration of our local heritage! Don’t miss out on the fun\, tradition\, and community spirit at the Silver Spurs Rodeo Parade. See you there!
URL:https://www.positivelyosceola.com/event/silver-spurs-rodeo-parade-2/
LOCATION:Downtown St. Cloud\, New York Avenue\, St. Cloud\, Florida\, 34769
CATEGORIES:Silver Spurs Rodeo
ATTACH;FMTTYPE=image/jpeg:https://www.positivelyosceola.com/wp-content/uploads/2025/01/Rodeo-Parade.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20250125T170000
DTEND;TZID=America/New_York:20250125T210000
DTSTAMP:20260501T080254
CREATED:20241223T002655Z
LAST-MODIFIED:20241223T002655Z
UID:10001878-1737824400-1737838800@www.positivelyosceola.com
SUMMARY:Winter Wonderland
DESCRIPTION:Come enjoy a festive evening in Downtown St Cloud! This event will feature guest pop up vendors\, food trucks\, music and some festive fun for the kids! \nFind winter themed photo ops available\, “snow” effects and a guest appearance from Frosty! Face painting and hair tinsel will also be available. \nShops will be open extended hours for the evening. Enjoy dinner and drinks from the downtown eateries.
URL:https://www.positivelyosceola.com/event/winter-wonderland/
LOCATION:Downtown St. Cloud\, New York Avenue\, St. Cloud\, Florida\, 34769
CATEGORIES:City of St. Cloud
ATTACH;FMTTYPE=image/jpeg:https://www.positivelyosceola.com/wp-content/uploads/2024/12/Winter-Wonderland.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20241222T100000
DTEND;TZID=America/New_York:20241222T140000
DTSTAMP:20260501T080254
CREATED:20240930T123610Z
LAST-MODIFIED:20240930T123610Z
UID:10001680-1734861600-1734876000@www.positivelyosceola.com
SUMMARY:WEEKLY Downtown St. Cloud Farmers Market
DESCRIPTION:Experience the charm of local and regional vendors offering a variety of local honey\, meats\, breads\, sweets\, coffee and more! Discover homemade and handcrafted goods while strolling through Downtown St. Cloud. Sip and shop\, explore the local stores\, unique boutiques and enjoy the diversity of downtown restaurants and bars.
URL:https://www.positivelyosceola.com/event/weekly-downtown-st-cloud-farmers-market-2/2024-12-22/
LOCATION:Downtown St. Cloud\, New York Avenue\, St. Cloud\, Florida\, 34769
CATEGORIES:Downtown St. Cloud
ATTACH;FMTTYPE=image/jpeg:https://www.positivelyosceola.com/wp-content/uploads/2024/09/Sunday-Farmers-Market.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20241221T140000
DTEND;TZID=America/New_York:20241221T190000
DTSTAMP:20260501T080254
CREATED:20241202T023334Z
LAST-MODIFIED:20241202T023334Z
UID:10001822-1734789600-1734807600@www.positivelyosceola.com
SUMMARY:Monthly Progressive Wine Walk
DESCRIPTION:Join for the City of St. Clouds monthly progressive wine walk! To join\, sign up here: https://www.eventbrite.com/…/wine-walk-in-the-cloud…
URL:https://www.positivelyosceola.com/event/monthly-progressive-wine-walk/
LOCATION:Downtown St. Cloud\, New York Avenue\, St. Cloud\, Florida\, 34769
CATEGORIES:City of St. Cloud
ATTACH;FMTTYPE=image/jpeg:https://www.positivelyosceola.com/wp-content/uploads/2024/12/St-Cloud-Wine-Walk.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20241221T090000
DTEND;TZID=America/New_York:20241221T100000
DTSTAMP:20260501T080254
CREATED:20241030T202109Z
LAST-MODIFIED:20241030T202109Z
UID:10001759-1734771600-1734775200@www.positivelyosceola.com
SUMMARY:St. Cloud Main Streets Historic Trolley Tour
DESCRIPTION:If you’re looking for St. Cloud’s best stories (and a few secrets)\, we have you covered on our Historic Trolley Tour. We’ll take you from our founding and on to present day. This tour includes several stops where you’ll discover the fascinating people\, places\, and moments that have made St. Cloud historically awesome since 1910. Discover how Main Street weathered the Great Fire of 1917 and the ever-changing times. Learn brief histories of the historical homes and unique architecture\, each one offering a glimpse into the past from the comfort of the trolley. One thing is guaranteed\, you’ll never look at St. Cloud the same way again. \n1st & 3rd Saturday monthly – 9:00am \n$25 Ages 18+ || $15 Ages 13-17 \nTours start at St. Cloud Main Street\, 903 Pennsylvania Ave\, St. Cloud\, FL 34769
URL:https://www.positivelyosceola.com/event/st-cloud-main-streets-historic-trolley-tour/2024-12-21/
LOCATION:Downtown St. Cloud\, New York Avenue\, St. Cloud\, Florida\, 34769
CATEGORIES:St. Cloud Main Street
ATTACH;FMTTYPE=image/jpeg:https://www.positivelyosceola.com/wp-content/uploads/2024/10/Trolley-Tours.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20241218T170000
DTEND;TZID=America/New_York:20241218T210000
DTSTAMP:20260501T080254
CREATED:20241202T024551Z
LAST-MODIFIED:20241202T024551Z
UID:10001825-1734541200-1734555600@www.positivelyosceola.com
SUMMARY:Downtown Monthly Market
DESCRIPTION:Enjoy the evening in Historic Downtown St Cloud. Find local makers\, artisans and food trucks while walking throughout the downtown. Shops open extended hours for the event along with eateries & bars to dine. This event has become a local favorite and truly brings the community together. It’s a great opportunity to get to know locally owned businesses and connect with local guest pop up vendors. \nRoads will be closed for this event which include: New York Ave & Pennsylvania Ave from 10th St to 12th St. City Hall parking lots & adjacent state streets remain open with parking available. The St Cloud Trolly funded by local businesses will also be offering free services for the evening. \nThis event is rain or shine. Hosted the last Wednesday of each month with the exception of November & December (hosted a week prior for holidays)
URL:https://www.positivelyosceola.com/event/downtown-monthly-market-2/
LOCATION:Downtown St. Cloud\, New York Avenue\, St. Cloud\, Florida\, 34769
CATEGORIES:City of St. Cloud
ATTACH;FMTTYPE=image/jpeg:https://www.positivelyosceola.com/wp-content/uploads/2024/12/December-Market.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20241215T100000
DTEND;TZID=America/New_York:20241215T140000
DTSTAMP:20260501T080254
CREATED:20240930T123610Z
LAST-MODIFIED:20240930T123610Z
UID:10001679-1734256800-1734271200@www.positivelyosceola.com
SUMMARY:WEEKLY Downtown St. Cloud Farmers Market
DESCRIPTION:Experience the charm of local and regional vendors offering a variety of local honey\, meats\, breads\, sweets\, coffee and more! Discover homemade and handcrafted goods while strolling through Downtown St. Cloud. Sip and shop\, explore the local stores\, unique boutiques and enjoy the diversity of downtown restaurants and bars.
URL:https://www.positivelyosceola.com/event/weekly-downtown-st-cloud-farmers-market-2/2024-12-15/
LOCATION:Downtown St. Cloud\, New York Avenue\, St. Cloud\, Florida\, 34769
CATEGORIES:Downtown St. Cloud
ATTACH;FMTTYPE=image/jpeg:https://www.positivelyosceola.com/wp-content/uploads/2024/09/Sunday-Farmers-Market.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20241208T100000
DTEND;TZID=America/New_York:20241208T140000
DTSTAMP:20260501T080254
CREATED:20240930T123610Z
LAST-MODIFIED:20240930T123610Z
UID:10001678-1733652000-1733666400@www.positivelyosceola.com
SUMMARY:WEEKLY Downtown St. Cloud Farmers Market
DESCRIPTION:Experience the charm of local and regional vendors offering a variety of local honey\, meats\, breads\, sweets\, coffee and more! Discover homemade and handcrafted goods while strolling through Downtown St. Cloud. Sip and shop\, explore the local stores\, unique boutiques and enjoy the diversity of downtown restaurants and bars.
URL:https://www.positivelyosceola.com/event/weekly-downtown-st-cloud-farmers-market-2/2024-12-08/
LOCATION:Downtown St. Cloud\, New York Avenue\, St. Cloud\, Florida\, 34769
CATEGORIES:Downtown St. Cloud
ATTACH;FMTTYPE=image/jpeg:https://www.positivelyosceola.com/wp-content/uploads/2024/09/Sunday-Farmers-Market.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20241207T100000
DTEND;TZID=America/New_York:20241207T113000
DTSTAMP:20260501T080254
CREATED:20241009T001430Z
LAST-MODIFIED:20241009T001430Z
UID:10001688-1733565600-1733571000@www.positivelyosceola.com
SUMMARY:The St. Cloud Chamber of Commerce and the City of St. Cloud Present the 61st Annual Christmas Parade
DESCRIPTION:The Annual Christmas Parade Presented by Orlando Health St. Cloud Hospital and the City of Saint Cloud along with Experience Kissimmee. \nThis Year’s Christmas Parade Theme is “Toys on Parade” \nThe St. Cloud Christmas Parade is a family-friendly event\, with festivities for all ages. This locally televised event will be live-streamed on the St Cloud Chamber’s social media pages.
URL:https://www.positivelyosceola.com/event/the-st-cloud-chamber-of-commerce-and-the-city-of-st-cloud-present-the-61st-annual-christmas-parade/
LOCATION:Downtown St. Cloud\, New York Avenue\, St. Cloud\, Florida\, 34769
CATEGORIES:City of St. Cloud,St. Cloud Chamber
ATTACH;FMTTYPE=image/jpeg:https://www.positivelyosceola.com/wp-content/uploads/2024/10/St-Cloud-Christmas-Parade.jpg
END:VEVENT
END:VCALENDAR