The Future of Downtowns Depends on More Than Just Storefronts, It Depends on Downtown Event Strategy

Visitors in Downtown Dover Delaware during the Fire and Ice Festival.

Across the country, from rural Main Streets to urban corridors, downtowns are facing a critical crossroads. While the past decade has seen waves of redevelopment and investment, many communities are still struggling with the reality of vacant storefronts, declining foot traffic, and evolving consumer behaviors. What’s often missing in these conversations is a recognition that physical revitalization alone isn’t enough — experience and engagement are equally vital.

At B-Side Events, we believe that a thriving downtown is more than its buildings; it’s the life that fills its streets, parks, and public spaces. And at the heart of that life is a well-crafted event and programming strategy. Events are not just entertainment they are economic engines, placemaking tools, and catalysts for deeper civic pride.

Why Programming is Essential to a Downtown’s Success

Events and activations serve as connective tissue between local businesses, residents, and visitors. According to Main Street America, every dollar invested in a Main Street district yields significant economic and social returns. But beyond the numbers, events create moments of shared memory, which over time, shape a community’s identity.

Downtown event strategy should not be viewed as one-off festivals, but as part of a larger strategy to build place attachment, enhance vibrancy, and support small business ecosystems. In our work, we’ve seen how events can transform not only perceptions but the economic trajectory of entire districts.

Case in Point: Vienna, VA and Dover, DE

In Vienna, Virginia, we partnered with the Office of Economic Development to activate the downtown through two community-first experiences: Passport to Vienna and Gingerbread Wonderland. These weren’t just seasonal events; they were designed as economic drivers and cultural touchpoints.

Passport to Vienna turned Small Business Saturday into an exploratory adventure, sending families across town in a “passport” scavenger hunt that highlighted local shops and public spaces. Gingerbread Wonderland became a key feature of Vienna’s Church Street Stroll, offering hands-on activities like gingerbread decorating and crafts that turned public spaces into family gathering spots. Together, these events brought measurable economic impact while reinforcing Vienna’s identity as a family-friendly destination.

Meanwhile, in Dover, Delaware — a community navigating decades of disinvestment — we worked with the Downtown Dover Partnership to produce the inaugural Fire & Ice Festival. This first-time event reimagined the downtown corridor as a life-sized winter art exhibit, blending public art, community programming, and local business engagement. The result? A groundswell of community pride, increased foot traffic, and a renewed vision for what’s possible as part of Dover’s 2030 Master Revitalization Plan.

Looking Ahead: A Blueprint for Downtown Event Strategy

As downtowns across America seek ways to rebound and thrive, events will continue to play a crucial role. Our recommendation to community leaders, business improvement districts, and economic development offices is clear:

• Anchor programming in local identity - Your community’s history, culture, and people should be reflected in the events you create.

• Design with small businesses in mind - Events should directly support downtown merchants and hospitality partners.

• Make collaboration a core value - Successful activations require partnerships between government, nonprofits, business owners, and community members.

• Iterate and Build - Events do not become successes over night, pick a few things you can do really well and build on top of them for future growth.

• Tentpole Events - Not every event has to be something large, a successful programming calendar includes major tentpole events and smaller activations to provide something for everyone.

Ultimately, events and programming aren’t just about filling a calendar — they’re about filling streets with life, joy, and opportunity.

At B-Side Events, we’re passionate about helping cities and towns unlock the full potential of their downtowns, one experience at a time.

Want to explore how events can strengthen your community? Let’s talk.