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Case Study

How Winter Haven Built a Community Calendar That Actually Reflects the City

A growing Florida city of 63,000 consolidated public, nonprofit, and internal events into one trusted platform, opened the door to ticketed fundraisers and ADA-ready communications, and trained its team in about two hours.

Winter Haven, Florida — Chain of Lakes
63,000+
Residents
2 hrs
Training Time
4+
Community Partners
The Customer

Winter Haven, Florida

Known as the Chain of Lakes City, Winter Haven sits on or around 50 lakes, and water shapes nearly everything about how the community lives, gathers, and grows. The city has purchased more than 500 acres of preservation land in the past two years alone, a signal of how seriously leadership takes the balance between growth and place.

Winter Haven has climbed from under 50,000 residents in the 2020 census to roughly 63,000 today. For years, city staff have described the pace as about six new residents moving in every day. A housing boom gave way to multifamily development, which has now handed off to commercial, diversifying the tax base and broadening what the city offers its residents.

Public Affairs and Communication sits at the center of that transformation. For the last four and a half years, Katrina Hill has led the department through a citywide rebrand, the consolidation of roughly seven separate department websites into one, and the buildout of enterprise tools that give staff consistent ways to create, publish, and communicate. The community calendar was the next frontier, and it was the one she was most hesitant to tackle.

The Challenges

What was holding them back?

A City Calendar That Only Showed City Events

Winter Haven manages hundreds of special events every year, but the city only published its own programming on the calendar. Anything run by a nonprofit, a partner organization, or a private host stayed off the site, creating confusion about ownership and outdated information.

A Growing Community With Scattered Information

Institutional memory does not survive a 25 percent population jump. Nonprofits scheduled events on top of each other, and residents kept saying there was nothing going on even when seven events were happening in a single weekend.

A History of Failed Calendar Attempts

Earlier efforts had been derailed by bots, spam submissions, and the lack of a tool that could give the city control while still letting partners contribute. For three years, Katrina pushed back on a community calendar without the right safeguards.

Fragmented Registration and Payment

Every department had its own registration platform, payment tool, and reporting process. Residents felt like they were dealing with five different businesses anytime they tried to engage with the city.

“We started to see a lot of nonprofits scheduling events over the top of each other, and so then everyone’s less successful. We started hearing a lot of, ‘there’s nothing going on,’ and we’re looking around going… we’re managing 7 special events this weekend. What do you mean there’s nothing going on?”

KH
Katrina Hill
Director of Public Affairs and Communication, City of Winter Haven
The Solution

One Trusted Calendar, Many Audiences

Guardrails That Made a Community Calendar Viable

Account-based event submission gave Katrina the control she had been missing. Partners can submit, but bots cannot. Winter Haven now runs a true community calendar that blends city, nonprofit, chamber, library, theater, and Main Street events without the spam that killed earlier attempts.

Custom Calendar Views for Every Audience

The homepage carries a clean view of city events and public meetings. The commission page shows commission meetings only. Sub-calendars like family-friendly events embed on webpages or share as a single link. Outside events live on the community calendar, filtered views live on the pages that need them.

One Payment and Registration Platform

Free events, small-ticket events like the State of the City dinner, and complex registrations like the cardboard boat race with its waiver requirements all run on one platform. Transactions land in finance in batches, clearly labeled by event.

A Resource Block That Builds Trust

A resource block at the top of the calendar page points residents back to official city channels. It has become a low-threat touchpoint in a moment where residents are increasingly asking questions in Facebook groups instead of going to the source.

An Employee Calendar Blending Training and Culture

HR was the first internal adopter. Mandatory training sits next to Mental Health Awareness Month events and cardboard boat race team sign-ups. Staff show up for required training and stay for the culture-building, without anyone duplicating events.

ADA Compliance Built Into the Workflow

Alt text is a required field when creating events for the City of Winter Haven, not an optional one. Staff feedback has been that the required field acts as a safeguard rather than a friction point, protecting them from accidentally posting noncompliant content.

“It [training] took maybe 2 hours with this platform. It was so easy. Other platforms I’ve onboarded here, I find that it usually takes about 2 years to get people comfortable with it.”

KH
Katrina Hill
Director of Public Affairs and Communication, City of Winter Haven
The Results

A Calendar the Whole City Actually Uses

📅

Training Dropped From Two Years to Two Hours

Katrina has onboarded a lot of tools in her tenure. Her benchmark for getting staff comfortable with a new platform is roughly two years. With the BeWith calendar, it took about two hours. The ease of use has extended to non-technical staff across departments, and partners consistently figure out event submission without a support ticket.

🤝

Main Street, Chamber, Library, and Theater on One Calendar

The relationships were already there. What was missing was the tool. Katrina's team loaded in the first quarter of events for Main Street and the Chamber, and both organizations now manage their own submissions. Nonprofits jumped on board because the tool is free to them, and the calendar has become the easiest boost their events can get.

🎫

Ticket Sales and Registrations Across a Wide Range of Events

State of the City ticket sales. A cardboard boat race with required waiver forms. An attainable housing event co-hosted with the county and a state agency. Even Down Syndrome Awareness Day, where residents purchased colorful socks through the platform and received them at the 5K race packet pickup. The flexibility has let Winter Haven get creative.

💳

A Finance Workflow That Finance Actually Likes

Transactions come in labeled by event, in batches that make reconciliation straightforward. A staff member can pull reports by budget line item and hand them to finance without rework. The workflow, once tested, became genuinely easy, and finance has received the calendar well because it simplifies their side of the equation.

Built-In ADA Compliance That Keeps Staff From Slipping

Alt text is a required field when creating events for the City of Winter Haven, not an optional one. Staff feedback has been that the required field acts as a safeguard rather than a friction point. Winter Haven is moving full steam ahead, treating the DOJ's ADA Title II timeline as if the original deadline were still in place.

“You’ve been the only digital platform we used that was willing to make alt text a required field. The feedback I’m getting from staff is, no, you’re safeguarding me from accidentally posting this without an alt text.”

KH
Katrina Hill
Director of Public Affairs and Communication, City of Winter Haven
What's Next

Looking Ahead

On April 30th, Winter Haven cut the ribbon on a $21 million Recreation and Cultural Center. The facility includes a double gymnasium, a free public gym, a zero-entry pool designed for first-time swimmers and wheelchair access, a splash pad, a branch library, a computer lab, a gaming room, a podcast studio, and open space for community events like a Juneteenth celebration featuring a car show and food trucks. A documentary film crew has been following the build for three years, and the finished piece will debut at this year’s State of the City.

The calendar is a core part of how that story reaches residents. A dedicated sub-community for the Recreation and Cultural Center will feature five to seven events each day, with the most important ones surfacing to the main calendar so the community knows the new facility is open and active. The employee calendar is in its next phase of adoption, with HR leading the way and departments like Parks and Recreation starting to plan Mental Health Awareness Month programming on the platform.

Jacqueline Vickers, Winter Haven’s new Community Engagement Manager, is taking ownership of the calendar as a primary tool for community outreach. The calendar has become her first touchpoint with nonprofits and community organizations, and the foundation for the deeper relationships that come next.

“My initial thought after the [BeWith] sales pitch was, this is too good to be true. There’s no way this solves all my concerns. It’s not, though. It’s not too good to be true. It is the tool that solves it, and it’s brought things to the table that I hadn’t even thought of.”

KH
Katrina Hill
Director of Public Affairs and Communication, City of Winter Haven

Want similar results in your growing city?

If your community is outgrowing the way it manages events, payments, and accessibility, Winter Haven’s story shows what a centralized, partner-friendly calendar can do when the tool finally catches up to the ambition.