Despina McLaughlin, President, City District Main Street

Invest: spoke with Despina McLaughlin, president of City District Main Street, about the advantages of her district that serves the downtown business corridor, its Downtown Orlando Field Day event that helped to “level the playing” field, and its efforts in promoting local artists and culture through its “Art Box” program. 

What is City District Main Street’s overall contribution to the Greater Orlando community?

There are about 12 Main Street programs within the Orlando city limits. We are connectors and liaisons between small businesses and the city of Orlando itself. We aim to help our small-business owners navigate everything from permitting fa§ade grants to pulling 18a special event permits. I like to call us the glue and an extension of resources that are available to our storefront businesses. We help small businesses get a leg up so they can ease into starting or running their businesses in our Main Street district. We can help them take care of things that we know business owners may not have experience with or time to navigate as it relates to city permit requests, code compliance questions, and optimizing grants to support their storefronts—while also driving foot traffic to their businesses, and uniting the rich downtown Orlando community. We measure our success by how we support and reinvest money back into our locally owned businesses, by our membership, and by our participation and volunteer hours accumulated over the year. We also fundraise and are constantly engaging with our community to provide us with qualitative and quantitative feedback. We are a safe place to help small businesses with what you need and to be an ally. Those are all big metrics of our growth and success.

What are the unique characteristics that define the neighborhoods that City District serves?

Our district is unique as it resides in the heart of downtown Orlando, at the center of the bustling downtown business corridor. Our district includes city hall, high-rise buildings, and a vibrant nightlife and entertainment hub. We have partners at KIA Center and other businesses just outside of our district boundaries, with whom we often collaborate (KUL Furniture, Orlando City Soccer, Hittn’ Skins). We serve business members during the day, as well as hospitality, vendors, and visitors at night. As we continue to drive people downtown and welcome more residents to the district, we want to be that warm extension of the city and showcase how incredible our neighborhood truly is.

How does City District incorporate arts and culture initiatives into its efforts in downtown Orlando?

We have a hand in supporting many of the murals that you see downtown, which are collaborations between city hall and local artists. You’ll notice that the intersection murals are branded in City District colors, and we are thankful to City Hall for really advocating to make sure we are incorporated into the artwork and fabric of the district. Furthermore, our Art Box program invites local artists to paint electrical boxes, which are now on nearly every corner in the district. This wasn’t possible for a while, but in the last year and a half, leadership has given us opportunities to incorporate more arts and culture. We did roughly ten different Art Boxes, where we purposefully employed local artists to ensure we were driving culture and authenticity while connecting artists with businesses to build relationships and connections within our neighborhood. It was important that we financially support our artists and show our appreciation through the continued work opportunities. We will continue to tap local artists as more boxes become available, and this program will be successful beyond anything we have imagined.

What collaborations does City District have with community organizations and government entities?

Our downtown community wants to be active and engage with their neighbors — they’ve told us this through multiple surveys. So, our small but mighty Main Street team went to work to deliver. In November 2023, we held our first Downtown Orlando Field Day, which is coming back this year (Nov. 7, 2024). We tested the waters for our businesses and audiences to engage in a playful and competitive space. It was a huge collaboration with local businesses to bring this event to life. We partnered with the Dr. Phillips Center for the Performing Arts, AdventHealth, Downtown Development Board, Red Lobster, Orlando Magic, Orlando Solar Bears, The Orlando Weekly, OUC, the Orlando Hospitality Alliance, City Beverages, CityArts, Out Sports League, WFTV and OCPS to deliver an incredible experience. We were proud because it leveled the playing field for many of our daytime visitors and nighttime visitors, and allowed them to all enjoy some team camaraderie and friendly adult competition, especially after COVID and the pandemic. We had 350 participants and are expecting to smash those numbers at the next event this November.

What initiatives are you excited about with City District?

It is really about working with our city leaders and finding ways to recruit, retain, and bring in businesses that our neighborhood wants. As a Main Street, we can pull our own weight, but we need to work with our city leaders to get where we need to go as we reimagine downtown. Retail is a big item on our list, as well as activating empty spaces and embracing the arts. We want a lot more art and music at every turn, and you can see this coming together currently with major support from the city. We are also very proud of our cleanup program every quarter that we started three years ago. We do beautification, graffiti removal, and pick up garbage along Gertrude’s Walk, along Orange Ave., and partner up with our sister main street, Parramore, to double up these efforts. We play a role in trying to keep this community green and clean. We also work to not overconsume energy or space. We work out of a coworking space (VentureX) and are very nimble and mindful of the resources we consume. With only one paid employee and 15 community volunteers filling our board, we all play an active role in optimizing sustainability or connecting with people who can do that for us and our businesses. We are an organization that is very mindful, and we make many decisions based on sustainability, supporting locals, and giving back to our district.

What are some of the main challenges that City District faces?

It has been challenging since COVID as our identity shifted from hosting a lot of events. It took some soul searching, as we had to figure out We are in such a unique space as many organizations overlap in our main downtown corridor. It is about finding our specific lane to ensure we are being complementary to one another and truly finding ways to collaborate and be resourceful, and how to best serve our business members while also remaining authentic to ourselves.

What are the goals and aspirations for City District in the near and long term?

We want to be a thoughtful neighbor to our downtown community and business owners and residents. We are here for those who have questions, need connections, or want to get involved. We want to be a friendly resource for everyone who resides, works, plays, drinks, or visits our district. We want people to join us for events and learn about the local artists who are participating in our Art Box program or join us for a cleanup — hear about ways they can get involved. It is a safe place and organization for people to care and to come together. We need to keep serving at a high level, and we strive for that over the long term. It’s our goal to expand our team, and we want people to volunteer and grow with us.