Where are Boston's best late-night food spots?

Jeremy Siegel: You're listening to GBH's Morning Edition. It is the early morning after a long holiday weekend. So, Paris, you want to get chaotic and talk about nightlife?

Paris Alston: I always want to get chaotic. Let's do it.

Siegel: Welcome back to Nightlife in Boston, a reporting collaboration with Axios Boston, where we are looking at the city's nightlife identity, what makes it good, what makes it bad, and what you think could make it better. And just a reminder that we still want to hear from you at GBHNews.org/nightlife or by text at 617-300-2008.

Alston: Today we're taking a bite out of crime. Okay, I'm just kidding. We are talking about late night food. And joining us in the studio for that is our friend and Axios reporter Mike Deehan. Hello, Mike.

Mike Deehan: Good morning.

Alston: And also with us is [Key Henson], a.k.a. @WannabeStayAtHomeDad on TikTok and Instagram, where he rates food at eateries around Boston and beyond. Welcome.

Key Henson: Good morning. Thanks for having me.

Alston: So Key is with us today because he and I recently went on a joyride through Boston, racing against the clock to hit as many late-night food spots as possible.

Alston (previousely recorded): My momma would like these. Mmm.

Henson (previousely recorded.): Right now I know it's scrumptious. I'm trying to put myself, like, fresh out of a bar. Like, this would probably change my life, you know what I'm saying?

Alston (previousely recorded): If I was, like, lit —

Henson (previousely recorded.): I would sit right here on this brick and then eat it.

Alston: So that is a snippet of us eating fried clams at like, what was that? Maybe 10 or 11 o'clock at night at Simco's in Mattapan. Yes. So, you know, it was a great time. You can watch the whole thing on the GBH News YouTube channel and check out some of the spots that we hit. And I'm getting hungry just thinking back to that fateful night.

Siegel: I'm getting hungry thinking about it, too. I wasn't with you, but watching that video, I mean, it really makes your mouth salivate. So right now, we have — what we have? Four people in the studio, which is, you know, way more than usual.

Alston: And no food.

Siegel: Four also, it almost feels like it's more than the number of places that are actually open until late night, reasonable hour in Boston.

Deehan: It might be about the same.

Siegel: Yeah. Before we get into like what you, Key, and Paris discovered on your late-night journey, I'm curious, like for everyone here, your description of the nightlife food scene, the late-night food scene in Boston. Deehan, I guess we'll start with you.

Deehan: Yeah, well, it's poor, certainly. You know, you have you have your options, I think, because especially during the school year, we're kind of dominated by the college kids, is kinda where the demand comes from. So maybe sometimes in those college areas, if you're close by there, you'll have some options. Obviously, in 2023, delivery and apps have really taken over a lot of that action. But if you want to go and sit down somewhere, you don't have that many choices aside from, you know, like a handful of diners and, you know, 24 hours, don't even think about it. You know, maybe you can get someplace that doesn't close, the kitchen stays open past 10, but you're going to be hurting for options.

Alston: I gotta to push back on you, Mike Deehan. Because I think as a result of this night out, I was with you prior to this, I was like, there's nothing I really want to eat after like midnight here. But the places we hit, including two 24-hour locations, South Street Diner, and then Bova's, in both Jeremy and Key's neck of the woods. But also Simco's was — I don't even wanna say —

Deehan: I didn't realize Simco's was open that late.

Alston: Me neither. Right. I guess you could say, an unsung hero of the late night food scene.

Deehan: Always a hot dog champion. But I didn't know late-night.

Alston: Yeah, but the clams. I was like, those clams, Key! I mean, were you surprised by some of the options we found?

Henson: For sure. For sure. I think being new to Boston, I've been here for around a year or so. I kind of fell into the perception that, you know, there's not a lot of options. And then we did that. And I'm like, there's options in each neighborhood that we went to, and we went from Hyde Park to East Boston, which was kind of crazy. But yeah, I think it kind of opened my eyes as well.

Siegel: Hitting all those places, do you have a number one late-night spot in Boston? For people listening, I mean, Key does these awesome reviews on TikTok where he hits like all of these places around Boston.

Henson: Yeah, usually during the daytime.

Siegel: What's your late night pick, then?

Henson: My late night is usually, you know, probably Bova's, just because I'm around the corner from it and I've got a big sweet tooth. And they also do like these chicken croissants at the end of the night. I don't even know if they're good, but usually they do what I need them to do.

Alston: Nice. Yeah. And Anchovies was another pick of yours that we ended up at, too.

Henson: Yeah. Anchovies in the South End is a good, kind of good dive bar feeling where you can, you know, you do get the chance to sit down and enjoy some food.

Alston: Mm hmm. But Deehan, to your point, right? We went to six spots, but that's only six. And if we wanted to extend the list a little bit further, it might be a little hard. And granted, it wasn't like each place we went to, I mentioned we were racing against the clock because they were going to close right around like 11 or midnight or something like that. And so what are some of the barriers to being able to have more options that extend further into the night?

Deehan: Yeah, it's kind of case by case. But if you take a look at when a restaurant says, oh, we want to extend our hours, what are the barriers there? And it's usually, you know, something like the licensing board or some other kind of, you know, piece of the city hall bureaucracy. And more often than not, if a place wants to extend their hours past midnight to 1 a.m. towards 3 a.m., sometimes they'll request it, especially in a student area, the police push back, say that they don't want a place open that late because of potential safety issues or incidents. The neighborhoods push back in a big, big [way] — they have a lot of sway with city hall — saying that, no, we don't want this place to be open at all hours or until 1 or 3. And they kind of win the day more often than not. It's not really the market that wins, because the market's there, but it is neighborhood associations, the police have a lot of pull. City councilors, representatives, people like that who will often side with the neighbors over, you know, the kids who want to eat some food.

Alston: We should point out, too, I think there was a recent piece in The Boston Globe that had the headline, like, is 4 p.m. or 5 p.m. the new 8 p.m.?

Alston: And it's like, Jeremy and I eat dinner at that time.

Siegel: Yeah, I mean, I was all for it. I was like, Oh, is everybody here an early morning host who has to wake up at like 2 a.m.? But it was about sort of the shift we've seen in culture, like post-pandemic of people getting earlier reservations and things.

Deehan: To get out of the house.

Siegel: Yeah.

Alston: Well we are all adjusting one way or another. I mean I think we can all agree though at any time is a good time to go get a Bova's cannoli.

Henson: For sure.

Alston: Well Key, Mike, thank you both so much. And again, if folks want to check out Key's food reviews, you can find him on TikTok and Instagram at the handle @WannabeStayAtHomeDad. Thank you both for coming in. And also, if we missed any place or if you want to add your thoughts on late night food, you can text them to us at 617-300-2008 or email thewakeup@wgbh.org. And for more on our nightlife series, check out GBHNews.org/nightlife, where you can also take our survey.

Siegel: You're listening to GBH's Morning Edition.