Bridget Law, Waldorf Strings<br />
Teacher

If you have spent much time in Boulder, chances are you have experienced something Stephen Oskay helped put together. From Bands on the Bricks and music festivals to arts and cultural events, Stephen’s work happens behind the scenes. From coordinating musicians, performers, vendors, and businesses, Stephen plays a large role in making downtown Boulder the lively cultural hub we all love.

In this Community Spotlight, Stephen talks with Gary Gutierrez of The Lesson Studio about what goes into creating Downtown Boulder’s events, his role in running Bands on the Bricks, the importance of supporting local musicians, and what he hopes people will see coming to downtown Boulder in the years ahead.

Q & A with Stephen Oskay1

Gary: For anyone who’s unfamiliar with everything Downtown Boulder does, can you give us a sense of the scope of it?

Stephen: Downtown Boulder Partnership serves a couple of functions in the community. There’s the Business Improvement District, so that’s the downtown commercial district, essentially around Pearl Street and the surrounding areas.

The Business Improvement District helps maintain a clean and safe program, maintenance and making sure that the community is clean. That’s the main function of the business improvement district.

And then we have Downtown Boulder Community Initiatives, which is the arm that I work with a little bit more closely, and that’s community engagement. Trying to make inclusive events that engage the community through arts and culture.

Gary: You came to Downtown Boulder after working at the Fox Theatre. When did you officially get involved with Downtown Boulder?

Stephen: I started working for Downtown Boulder in March of 2022 after the pandemic. I came on originally as an event contractor with them, just kind of doing the operation side of stuff, and over time took on talent buying, became a staff member.

Currently, I’m the Event and Operations Manager for them, and I’ve still been growing with them over the years, just trying to take on as much as I can.

Gary: So what does a typical day look like for you?

Stephen: It really depends on whether we’re in the middle of an event or getting ready for an event. There’s a lot of just kind of communication and coordination between all the different
stakeholders.

Whether that’s our staff figuring out what serves the businesses down here, coordinating with the various operational vendors, the musicians that we book for our events, the performers, and,
outside of the kind of mundane day-to-day stuff, trying to think of unique ways that we can activate the downtown and experiences that we can give to people down here.

Gary: That seems like a lot of different pieces to keep moving at once.

Stephen: Yeah. There’s a lot that goes into it. You have the operational side, but then there’s also the creative side of thinking about what we can do next and how we can make the
experience better. A big part of it is figuring out how all those pieces work together. We’re working with businesses,vendors, artists, performers, and the community, and we’re trying to make something that works
for everybody.

Gary: What are some of the things coming up that you’re especially excited about?

Stephen: There’s a lot of things on the horizon for Boulder in general. We’re working with Tulagi Festival to help put that on at the end of August, which we’re very excited about. It’s going to be 20 different venues up and down the mall. We’re activating the bandshell. Lots of great national acts are going to be playing, and it’s kind of a unique format for Boulder, at least. We’re excited to kind of expand on the stuff that happened last year.

And then next year we’re really looking forward to the Pearl Street 50th anniversary.

Gary: What’s the plan for the 50th anniversary?

Stephen: The 50th anniversary is going to be a year-long celebration. The height of the programming will be kind of around late July, early August. It’s not one thing that we’re doing. Whether we’re doing our Snowflake Express rides, the Tebow train, the way we program bands, or what we bring to other downtown events, it’s going to be
something that people see throughout the year.

Gary: So people will see pieces of the celebration throughout a lot of the existing downtown programming?

Stephen: Yeah. Any events that we are having will be part of the celebration. Band on the Bricks, Pearl Street Arts Festival, other events that are downtown, like World Singing Day and things like that. They’ll all have this element incorporated into them.

As far as the actual celebration, those details are still to come.

Gary: Of all the events you’ve worked on, is there one that has become your favorite?

Stephen: I mean, I’m biased because Bands on the Bricks is my baby at this point. So Bands on the Bricks is my favorite event that I do. I really like booking the variety of music that we get, seeing the community come out and really kind of have fun and have a certain space that they can hang out at.

It’s a really fun kind of community party.

Gary: For someone who hasn’t been to Bands on the Bricks in a while, what can they expect besides the music?

Stephen: We have food vendors. It’s the kind of typical fare that you’ll find downtown on our evening night. We have Chiri’s Momos, Fast Eddie’s hot dogs, La Catrina Tamales, a delicious tamale cart down there. As far as drinks, I’m on the bar program for them as well, and we offer a wide variety of cocktails. This year we had some hard ginger beers, mules, margaritas, some non-alcoholic beer options, weekly beer sponsors. We try to offer the whole package.

Gary: And you really enjoy the music side of it?

Stephen: Yeah. I really like booking the variety of music that we get. That’s one of my favorite parts. And, it’s great seeing the community come out. That’s what makes it really rewarding. You get this variety of music, you get all these people coming downtown, and they really kind of have fun and have a certain space that they can hang out at.

Gary: You also work with a lot of local musicians. What role do these events play for artists?

Stephen: We have a ton of local artists involved. With Tulagi, for example, it’s a really great resource for local musicians to kind of get out there and network. There’s lots of great talent in there. That’s something I really enjoy about putting these events together. You get to bring in national acts, but you also have all this local talent and give people opportunities to get out there and be part of it.

Gary: What about people who want to get involved behind the scenes? Are there volunteer opportunities?

Stephen: Yeah, I really love you guys to point people to our volunteering opportunities. We’re always looking for more. If you go to boulderdowntown.com, you can check out our events and our volunteering opportunities. The website also has job openings and stuff like that. It’s a great resource for anybody. There’s a job board, there’s an events list, calendar, volunteer opportunities. So really anything Downtown Boulder, find the Boulder Downtown website.

Gary: What about a young person who’s really into music? Maybe a high school student who wants to get some experience around events and artists?

Stephen: I would say the arts festival would be a great fit for high school kids. They can help our artists, whether it’s booth sitting or helping them run water or things like that. There’s also networking. It’s cool.
And in the winter, we have our holiday events that we’re always looking for volunteers for, whether it’s the Lights of December parade or our Switch on the Holidays events. For the musical events, I do typically need volunteers for Bands on the Bricks, but they would have to have a parent there as alcohol is involved.

Gary: That’s a pretty great way for someone interested in music or events to see what actually happens behind the scenes.

Stephen: Yeah, definitely. There’s a lot that goes into these events that people don’t necessarily see. Getting involved is a good way to see how everything works and to meet people.

Gary: With everything you’ve got going on, what do you hope Downtown Boulder continues to be?

Stephen: I think it’s about continuing to find unique ways that we can activate the downtown and experiences that we can give to people down here. That’s really what I enjoy about the job. You have all the logistics and all the coordination, but at the end of the day, you’re trying to create something that people want to come to, participate in, and remember.

And I think that’s what makes it fun.

Learn More and Get Involved

Downtown Boulder: Events, community programming, volunteer opportunities, and everything happening downtown.
Bands on the Bricks: Live music, food, drinks, and a summer community party on Pearl Street.
Tulagi Festival: A multi-venue music festival bringing national and local artists throughout downtown Boulder on August 27-August 30, 2026.
Pearl Street 50th Anniversary: A year-long celebration with special programming and events throughout downtown Boulder starting January 2027.
The Lesson Studio: Performance-based music education in Boulder