Downtown St Cloud Events

Downtown St Cloud Events Local events happening in Historic Downtown St Cloud, FL. Updated regularly with community organized events and details.

Wine Walk in the Cloud returns this October! Join us for this wine crawl through Historic Downtown St. Cloud that’s sure...
09/15/2026

Wine Walk in the Cloud returns this October!

Join us for this wine crawl through Historic Downtown St. Cloud that’s sure to be a spooktacular event! Bring your tribe & come dress in your best costume.
Purchase your passport ahead of time:
https://www.eventbrite.com/e/wine-walk-in-the-cloud-tickets-1979600562572

Please contact event host, The Black Squirrel Bookstore directly for any specific questions. Follow Wine Walk in the Cloud for more updates.

Saturday, October 17, 2026
2:00pm-7:00pm
Historic Downtown St Cloud, FL 34769

Thank you I.O.O.F. - St. Cloud Lodge 66 for being a Downtown Business Group Member. Your support to the businesses & eve...
09/11/2026

Thank you I.O.O.F. - St. Cloud Lodge 66 for being a Downtown Business Group Member. Your support to the businesses & events downtown is appreciated.

Find more information in their QR link.
Located at 1122 New York Ave, Downtown St. Cloud,FL 34769

Enjoy some long time favorites and a few new menu items this season from Sweet Spot Snoballs — dirty soda & popcorn now ...
09/05/2026

Enjoy some long time favorites and a few new menu items this season from Sweet Spot Snoballs — dirty soda & popcorn now available!

Located at 1124 New York Ave, Historic Downtown St. Cloud FL 34769.

The Post Where coffee, tea & faith gather. Stop in their cafe and enjoy a drink, their baked goods and shop their gift s...
09/04/2026

The Post
Where coffee, tea & faith gather. Stop in their cafe and enjoy a drink, their baked goods and shop their gift shop.

Located at 1005A New York Ave, Downtown St Cloud, FL 34769

09/03/2026

Wine Walk in the Cloud returns this fall!

🍷 🥂 🍷 🥂

Saturday, October 17th 2:00-7:00pm
Join Wine Walk in the Cloud - Adult Halloween Edition!

🎃 Purchase your passport ahead of time - find the Eventbrite Passport here:

https://www.eventbrite.com/e/wine-walk-in-the-cloud-tickets-1979600562572

Arrive wearing your favorite costume & spend the afternoon sampling wine while you explore Downtown St Cloud. participating retail shops will also have special discounts & giveaways for passport holders.

Pick up your passport, map, wine glass the day of the event inside The Black Squirrel Bookstore . Located at 1118 New York Ave.

09/03/2026

Nothing excites us like the feeling of Downtown Monthly Market season returning! Mark your calendar, set your reminders and make plans to attend. Historic Downtown St. Cloud will be hosting over 100 vendors including: food trucks, local makers, bakers, crafters & live music. This event has something for everyone & is a perfect opportunity to get aquatinted with the local community & support a wide variety of local businesses.

Wednesday, September 30th
5:00-9:00 PM
Historic Downtown St. Cloud, FL
*Road closures begin at noon*

🎃 Get ready, St. Cloud — Halloween is taking over Main Street! 👻Join us on Saturday, October 31 for A Night of Maniacs &...
09/03/2026

🎃 Get ready, St. Cloud — Halloween is taking over Main Street! 👻

Join us on Saturday, October 31 for A Night of Maniacs & Witches: St. Cloud Main Street Trick & Trunk or Treat in Historic Downtown St. Cloud!

🍬 5 PM–8 PM | Trick & Trunk or Treat
Bring the kids, costumes, and candy bags for a fun, family-friendly evening as downtown shops, businesses, and decorated trunks hand out treats.

🧙‍♀️ 8 PM–11 PM | Maniacs & Witches Block Party
When the sun goes down, the party turns up! Stick around for music, dancing, costumes, vendors, and a hauntingly good time in the heart of downtown.

Come dressed to impress, bring your crew, and make a full night of it with dinner, shopping, and Halloween fun on Main Street.

📍 Historic Downtown St. Cloud
📅 Saturday, October 31
🎃 Trick & Trunk or Treat: 5–8 PM
🕸️ Block Party: 8–11 PM

Come for the treats. Stay for the thrills.

Estate buying event hosted at Dave Askew Jewelers September 15th-17th from 10:00am-5:00pm.Find them located at 1121 New ...
09/02/2026

Estate buying event hosted at Dave Askew Jewelers September 15th-17th from 10:00am-5:00pm.

Find them located at 1121 New York Ave, Downtown St. Cloud, FL 34769

Join in the fun this week The Black Squirrel Bookstore — Adult Glow Bingo this Thursday night 7:30-9:30 (check-in at 7pm...
09/02/2026

Join in the fun this week The Black Squirrel Bookstore — Adult Glow Bingo this Thursday night 7:30-9:30 (check-in at 7pm).

Find them located at 1118 New York Ave, Downtown St. Cloud FL 34769

Land Title Professionals LLC- thank you for your membership and support to Downtown St. Cloud. Find their team located a...
09/01/2026

Land Title Professionals LLC- thank you for your membership and support to Downtown St. Cloud.

Find their team located at 1105 Pennsylvania Ave, Downtown St. Cloud, FL 34769
Contact them for all your local Real Estate needs.

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Saint Cloud, FL
34769

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