Portland is…BOLD


Casey Gilbert – Executive Director

“I think that people here are unafraid to be who they are; I think Portland is unafraid to be who it is. People in Portland are so different and unique and vibrant. You just walk down the streets and you can see that people are living true to who they are.”

Personal Insights

How long have you been in Portland and how has it changed since you’ve been here?

I’m a newbie to Portland, so within the two years that I’ve been here, I’d say it hasn’t changed a whole lot. The one thing that I can tell is changing is that more and more businesses — whether it be retail businesses, restaurants, or even large businesses like WEX, which is now a billion dollar business — want to be downtown. This trend comes as no surprise since Portland is such an amazing place to live, work, and play!

What is your favorite Portland trend?

Portland to me is one of the most authentic and friendly places that I’ve been. People want to help and people are genuinely interested in you. I always tell this story about before I moved to Portland: I came up to visit to job hunt and house hunt and I went to a little restaurant in the West End called Hot Suppa. I ordered the grilled cheese and tomato soup, which is probably the best grilled cheese and tomato soup that I’ve ever had, and it comes with a side of pickles. It happened to be bread and butter pickles, which I don’t particularly care for. The server came over and asked me how my meal was, and I said, “I don’t like the pickles,” or “Are these bread and butter?” She could have just left it at that, but she said, “What kind of pickles do you like?” And I said “Dill pickles,” and she said, “Well our chef pickles all types of pickles, so let me go in the back and see if he has any of his dill pickles.” And she brought me out dill pickles. It’s a small, simple gesture, but it really captures the essence of how people are in Portland. People are helpful and friendly, and want to make other people feel happy.

What makes Portland special to you?

There’s something about this balance between having it feel very urban — and having all the benefits of big city life — but also feeling small and manageable enough that it feels like a small town community. I can walk down the street and recognize people, I don’t feel like I’m getting lost in the mix; yet we’ve got James Beard Award winning restaurants, and we’ve got beautiful historic buildings, and modern buildings, and walkability, and a great art museum. So all the things that people love and think about in an urban core, we’ve got it — but it still has that small town essence that I love, the community vibe.

Portland Downtown

How would you describe your job at Portland Downtown?

My job at Portland Downtown is multifaceted. On the one hand, I’m a problem solver. On the second hand, I’m a convener. And I would say maybe on the third hand, I’m the strategic thinker/visionary. I’ve got to keep everybody moving forward, working on our strategic plan. I help bring everybody together: the committees, the board, the staff —  and keep everybody moving towards that vision. And then along the way, that’s not always going to be the most smooth process so problems will arise and challenges will arise and so it’s my duty, and my job, and my pleasure, to take the challenges, solve those problems, and make those challenges seem as insignificant as possible, and whenever possible, turn those challenges into opportunities.

Can you please describe a notable program that Portland Downtown is involved with?

Something that I think is really unique is Pandora’s Winter Lights. So, as you know in New England, in Maine, the winters are very dark and very cold. Pandora’s Winter Lights were seen as a way to brighten up the dark months during daylight savings time. Pandora LaCasse is a local artist and it all started out with just asking her if she could do a couple of light sculptures. It has blossomed into these beautiful light sculptures hanging from the street poles up and down Congress Street as well as Longfellow Park, Congress Square Park, Tommy’s Park, and Boothby Square. I think people actually come to Portland to see the Winter Lights, and it really brings happiness and joy to people. It’s a program that we are happy to fund.

What is something you think most people in the area don’t know about Portland Downtown?

I think there’s a lot that people don’t know about what Portland Downtown does behind the scenes. I think coming on board as Executive Director, I’ve really made it my mission —  and the staff has made it our mission — to let people know what we’re doing 365 days of the year to keep downtown clean, safe, and vibrant. A lot of people first know us through some of our largescale events like Merry Madness or Old Port Festival, and they don’t know that we’re the ones out there operating the street vacuums making sure that downtown is free of cigarette litter. They don’t know that we’re the ones that actually do snow removal in the winter. Maybe they think magical snow removal fairies do it but it’s actually Portland Downtown. So it’s really our jobs to better educate the public and create awareness of what we do behind the scenes. When people do find out about all the wonderful things that we do, they’re very surprised and thankful.

People and Places

What is the most beautiful spot in Portland to you?

We have so many, but inside the district, there’s a couple of really sweet secret gardens. Behind the Longfellow House is the Longfellow Garden, and then right next to the First Parish Church is a beautiful garden that is open to the public during the day as long as the gates are open. Outside of our little downtown (but still on the peninsula) is the absolutely gorgeous Eastern Prom. It has sweeping views of the bay and the islands and so much green space and tons of places to picnic. And there’s even a swing set, so you can be on the swings while you’re looking at the ocean.

What is your favorite dining place in Portland that everyone should know about?

So many. I can’t just name one. Union Restaurant in the Press Hotel has just the most outstanding service, the most outstanding food, the most beautiful design. And a fun fact about Union is that if you sit at their bar on Fourth of July, you can actually see the fireworks that are happening on the Eastern Prom up on Munjoy Hill. My favorite bite in Portland is the pork bun at Pai Men Miyake. It is absolutely delicious; you have to have a food moment. Then I would say one of my favorite places in the summer to sit outside on a deck and have an adult beverage is the Novare Res Bier Cafe, which is another one of those great hidden spots!

Where’s a place one should go for a taste of culture?

So many options. That’s one thing I love about Portland: there are so many opportunities to get engaged in the community and in other cultures and experience art and music. So I would say everything from the Portland Museum of Art to Mayo Street Arts to the Merrill. On any given day, you can find performances that showcase world music and beautiful talent from around the country. And what I would also say is if somebody had time to volunteer, we have amazing nonprofit organizations such as ILAP, The Telling Room, and The Boys and Girls Club. All of these organizations serve some of our more vulnerable populations — including the immigrant community. Volunteering is one way to immediately expose yourself to other cultures in a very different way than just seeing a performance of world music. Get in there, have a conversation, help a kid learn to read, help a family understand banking, help them navigate downtown and the complexities of finding their way on the Metro bus. Whatever it is, that’s one way to get really deeply engaged in culture aside from just watching a performance. But luckily here in Portland, you can do both.