By Derek Reimherr
Whenever you move to a new city, one of the most important things you can do is find a few “spots” and become a regular. For us, we love a couple restaurants called Saus and The Tap Trailhouse, an improv theatre called Improv Asylum, and Harpoon Brewery.
Our most recent addition to the list came by way of our friends Collin (who’s guest posted on Millennial Marriage here and here) and Kate. After a dinner out in the city one Saturday night, they suggested we head to a German-style beer hall called Jacob Wirth in Boston’s theatre district, right on the edge of Chinatown.
This place is great. There are banners and beer everywhere, and it really has a nice pub feel. Plus, there was a live performer playing piano and singing who was hilarious. So we kept coming back.
After a few visits, we got to know that Saturday night performer as Alissa and became regulars of hers (at least in our eyes). We started following her on Instagram and learned she was Miss Massachusetts. Finally, after a few draughts of liquid courage, I decided to ask her for an interview. Because who doesn’t want a woman as cool as Alissa featured on your blog?
Read on to learn all about Alissa’s journey juggling school, pageants, Miss America, and performing music all around the New England area.
Maggie: Thanks for talking with us, Alissa! Before we get into who you are now, tell us a little bit about yourself growing up.
Alissa: Well, I was actually born in Rhode Island and moved to Massachusetts where I lived for most of my childhood. I’ve been playing the piano since I was 4 years old and I actually grew up in a family of professional musicians. There was absolutely no way I was getting out of it.
When you’re 5 years old, you don’t want to practice. I was very lucky to have a patient dad who was willing to sit with me and practice, even when I was whining. Obviously, it’s the greatest gift he could’ve given me.
Maggie: Did he teach you how to play?
A: Yeah, for the most part. He did take me to a teacher because when you’re that age, you’re more likely to listen to an official teacher. But he was still the one sitting down with me every night for practice.
Derek: Now for an important question...where were you on the awkward-popular spectrum growing up?
A: It’s actually funny - you’re not the first person to ask me this. I went to a really small high school. There were only 40 kids in my graduating class, so there weren’t the normal cliques. My high school was really competitive actually. All the kids were major overachievers participating in sports, drama, or whatever.
Derek: So what were you? What did you do?
A: I did pretty well in school. I had two claims to fame - I was the captain of the mock trial team.
Derek: Watch out!
A: No really, though! We won the state championship one year and were a finalist every year. I was also really good at tennis. I was the #2 player my freshman year and by senior year, I was first team all-state.
Maggie: So after high school, you went to Harvard for undergrad. What was that like?
A: So the weirdest thing was going from 40 kids to 20,000 students that were just as competitive as I was accustomed to. It was an adjustment. There were a lot of times where I’d look around in my classes (my concentration was government) and think, “Wow, there’s a pretty good chance some of these kids will be senators or congressman, maybe really jerky lawyers. Statistically, maybe even presidents.”
On the weekends, I was performing. I didn’t go to many parties or football games. Sometimes, kids from class - people I sat next to - would come in some place I was performing and not recognize me. They’d be like, “Who are you?” I was basically Hannah Montana.
Derek: It’s funny you mentioned being at Harvard and feeling like everyone is normal people...Maggie experienced the same thing working there.
So we read on your blog that you really just started doing pageants not long ago. Can you tell us more about your decision to give it a shot?
A: Yeah, it was about a year and a half ago. One day at work - I worked at a music shop - this woman came in and confused me for a girl that competes locally. She goes, “Oh, you should look into it! You might be interested.” I was pretty hesitant, but I did a Google search and read more about it. I learned the Miss America organization is the largest scholarship provider in the world. Even though it felt out of character for me, I thought it would just be a great opportunity to perform.
So I tried it and I won my first title as Miss Tri-County (area southwest of Boston). After that, I went for Miss Massachusetts and got 4th runner up. Good, but I could do better. So the next year, I entered and won the Miss Cambridge pageant. From there, I went for the Miss Massachusetts pageant again in the summer of 2016. And I won! A few months later, I was shipped off to Miss America.
Derek: What did your family and friends think of you entering the pageant world?
A: They definitely thought it was weird at first. Like I said, it was out of character. I was always a tomboy growing up. You guys have seen me perform before - it doesn’t seem very pageant-like. By the end of it, though, they were all on board. No one was saying, “This is a bad idea.”
Maggie: Tell us about the Miss America process. How did it feet participating and making Top 15?
A: We went to Atlantic City two weeks before the competition began. Rehearsals, outings, appearances, publicity. Sometimes we were up at 5am and not back at the hotel until 10pm at night. But I had a great roommate in Miss Montana. I definitely lucked out in that area.
Anyway, Massachusetts isn’t known for it’s good track record with pageants. It’s usually southern states. So when I made the Top 15, it was really exciting for me and anyone else who wasn’t watching the Patriots game.
Maggie: Wait, so do you find out before you make the Top 15?
A: No, no! You find out live on TV. Nothing is faked, totally real.
Derek: What is life like post Miss America?
Alissa: The biggest thing was, “Now what?” I spent all this time preparing and now I just...wasn’t. It was also the first time in my life where I wasn’t in school. I keep busy as Miss Massachusetts, though. I have parades, appearances at schools, performing, speaking. Solving world peace. You get the idea.
Derek: So this might be awkward...Does winning the title pay? We have no idea.
A: In Massachusetts, it’s not as lucrative as other states. But I did win a $12,000 scholarship to go back to school, I get paid for appearances, and I have some sponsors as well - haircuts, clothes, gas paid for the year. It’s pretty cool!
Maggie: When you’re not being Miss Massachusetts, what do you do in your spare time?
A: As you know, I’m a professional musician. I perform 3 or 4 nights a week. I’m also a music teacher. So there’s always lesson plans, new songs to learn, and emails to respond to. It can be mentally draining, but I really love performing and I love music. I also do a lot of volunteer work.
Derek: Can you tell us more? We read somewhere you were involved in a non profit related to music and pianos. What organizations do you volunteer with?
A: There’s Girls Rock which provides programs and camps for girls in at-risk community to help empower them through music. I also volunteer as a weekly music teacher at a school that doesn’t have a music program. It’s really important to me to always have a way to give back to the community.
Regarding the other question, Changing Keys is the name of my organization. After a semester of volunteering at a school, I would ask, “Now what? How are these kids going to progress after I’m not coming every week?” I started Changing Keys with the idea that one piano can create a thousands musicians and a thousand possibilities. So I find unused pianos and connect them with communities - churches, schools, community programs, anywhere that helps kids improve.
I find a lot of pianos through word of mouth, but nowadays I actually have more pianos than I have places to put them. It’s a great problem to have.
Maggie: So cool. Back to your musical career. What else do you play? Do you write and record any of your own music?
A: I mostly stick to the rhythm section: bass, some drums, and piano. No wind instruments for me. My sister is actually really involved in music production, but it’s not as much my thing. I do some basic stuff in Garage Band just so I can hear how I’m progressing. But when I write my own music, I’ll go to a studio.
Derek: *Changing keys* a little bit…what’s next? We saw on your blog, you mentioned law school.
A: I’ve thought about this a lot recently. Law school initially made sense; I was a mock trial champion after all. But it just didn’t seem like the right decision for me now. Eventually, I’ll go back and pursue copyright law working on behalf of entertainers using my Miss Massachusetts scholarship.
That being said, I really love performing. I don’t want to look back and feel like I didn’t pursue this fully in my 20s because I rushed back into school. Law school isn’t going anywhere, but my performing opportunities may not always be available.
Derek: Absolutely. It’s always best to take time and make sure you’re doing what you really like. We feel you.
A: Real quick, I have to say, it is so strange talking to you guys during the day. It’s like the first time you saw a teacher outside of school.
Maggie: Yeah...we typically aren’t drinking liter sized beers during the day. You’re getting normal Maggie and Derek. So to wrap things up, you’ve really seem to have accomplished a lot in a short time. How old are you again?
A: I’m 21.
Maggie: Wait, really? We thought you were at least 23 or so. Wow...so at 21, do you feel like you have a badass resumé? Do you feel like you have awesome icebreakers at parties?
A: Huh, that’s a good way to put. I’ve never thought about it that way. I have done a lot of cool stuff, but I have had to sacrifice a lot of social opportunities. I’ve missed weddings and events with friends. It definitely comes with a price that most people don’t see.
Derek: Yeah, that’s big! I think there’s a tendency as Millennials to not have a firm grasp on what life is really like when you’re working full-time.
A: Right, even things as silly as New Year’s Eve. I miss out on that with friends, but it’s worth it for what I love.
So true. Well thank you so much for taking the time to chat with us Alissa. We’ve really enjoyed it!
A: Definitely! This officially makes us best friends.
If you want to learn more about Alissa’s journey, you can follow her blog or check her out on Instagram (@alissamustomusic). For more information about her nonprofit, Changing Keys, check out its website or follow along on Instagram (@changingkeys).
For our part, we’ll be seeing her at our favorite stop in downtown Boston real soon.