Traveling Alone to Concerts: Finding Your Community on the Road

What if solo travel started with a concert ticket?

In Episode 8 of Roam Alone, I’m joined by Molly — the ultimate concert queen — who travels solo to cities across the country (and now internationally) to see her favorite artists live. I first met her at a Jon Batiste show, proof that live music and solo travel are powerful tools for connection.

Molly shares how traveling alone came about organically and how planning trips around concerts became her gateway into confident, independent travel. For her, attending concerts solo isn’t lonely — it’s one of the easiest ways to meet new people, build community, and create meaningful travel experiences.

If you’ve ever hesitated to travel solo or attend an event alone, this episode will inspire you to buy the ticket — and trust yourself to go.

Time Stamps
00:00 Meeting Molly at a Jon Batiste concert
04:43 How solo travel came about organically
07:02 Developing new friendships while attending concerts solo
09:20 First international solo trip to celebrate turning 50
13:00 Molly’s best solo travel safety tips

Roam Alone is hosted by Theresa Stephens.

Instagram: @theresaannstephens

Facebook: /theresastephens

Facebook: /RoamAlone

Transcript

Theresa Stephens So my guest today is Molly Connor. Welcome, Molly.

Molly Conner Hi. Thank you so much for having me. It's so good to talk to you again.

Theresa Stephens You too. So here's the story with Molly and me. We met. I believe it was

October of last year. Right? I live in Louisville and wanted to go up to see John Batiste, who

was playing at a concert at the Taft Theater in Cincinnati. And I didn't know anybody that

wanted to go. And I was like, you know what? I'm going to go anyway. So I get to the show, it's,

you know, the lights are already down. And it was about to get started. And in my row there's

like, I don't know, five or six empty seats, except for this very cool woman on the end with

these very cool glasses that stood out to me. And we stood beside each other the whole night

and ended up having such a blast together.

Molly Conner Yeah, it was so fun. Well, his energy just suits that kind of interaction.

Theresa Stephens Absolutely. And when he comes down the aisle and, you know,

everybody's following him around at the end of the show. It is such a blast.

Molly Conner Yes, yes.

Theresa Stephens So you also attended the show from another city. So give us a little bit

about your background.

Molly Conner I did I am, um, a hundred miles the other way from Cincinnati, in Indianapolis.

And, um, for that show, I was actually originally supposed to be in Europe, and the trip got

canceled. I was bummed that I wasn't going to be able to go to the show. I actually went to

college in Cincinnati, so I have quite a few friends there. Um, but it was a Tuesday night and it

was like, I'm not in Europe, I'm going to go. So I bought a solo ticket, unbeknownst to me,

would be next to you and headed down there, got some dinner and, um, ended up at another

great show. I had seen him earlier that year and it was just a real life changing thing. Yeah. So

I live in Indy, I work in marketing, I have a real flexible job and have sort of leaned into this

saying yes to things that feel like a good idea and not waiting around to find somebody else to

go with. And it's actually worked out to be pretty great.

Theresa Stephens Yes. And that's, you know, that's the key that I hear from so many people

that I have talked to about this, which is they're tired of waiting for somebody to go with them or

to do the things that they want to do. And you reach a certain point and it's like, you know

what? I'm going to go anyway. I'm not going to wait anymore for anyone else to come with me.

Molly Conner Well, and that's sort of how I feel. I turned fifty this past year. I'm finally in a

place where I can say yes to things and do what I, you know, suits me. And I have so many

great friends that I love to travel with, and I love to go to concerts with my three best friends.

And I have taken the opportunity to turn a concert into an annual week long weekend trip. But

really, at this age, people have kids, people have jobs, people have busy lives and can't just go

to Cincinnati on a Tuesday or hop on a plane to Boston on a Monday. and it was a lot of mefeeling like I was just missing out on things and then being, like, almost a little resentful that I

didn't just say yes. So it's been really freeing to just give myself permission to do that. And I

was saying the other day, Teresa, I think there's three things that I, that I can think of where

this happens. It's concerts, it's sports, and then probably church where everyone there has

agreed to a collective experience. So when you get there, I knew that by nature of you being at

this concert, you were a fan and it was something I could ask you about. Have you ever seen

this guy before? And so it really lends itself to just striking up conversation. Now that's not for

everybody, but you have kind of agreed to a collective thing that you're all doing together, and

it makes it a little bit easier to start up a conversation.

Theresa Stephens Wow. I love that perspective. That is the first time I've heard it expressed

like that. And it's exactly right. You know, whenever I've gone someplace alone, There's always

a part of me that is seeking connection. And I agree. With circumstances like a concert or

some kind of sports, it is a collective feeling and being around people who are enjoying it just

like you are. You know that excitement is. It is a collective feeling, I love that.

Molly Conner Exactly. The only other place I always say is an airport bar, because if you're at

the airport bar, you're either going somewhere or you're coming from somewhere. So you can

just say to someone, hey, what's your story? Where are you headed?

Theresa Stephens So tell me about the very first time you ever really traveled solo. What

inspired you to finally take that plunge?

Molly Conner Well, it's interesting because I kind of hybrid my way into it, kind of

unintentionally. I dated a guy probably a decade ago, and at the time I was working for myself

and could pretty much work from anywhere. And he traveled a ton for work. Um, it was a long

distance relationship, so it became very easy to just tag along on his trips. But what would

happen is I would get there and he would be busy. He would have meetings all day. He would

have a work dinner at night. And ultimately we would end up, you know, at the end of the night,

meeting up for drinks. But it allowed me to do a lot of solo exploring. It was kind of the best of

both worlds. We went to New York City a lot, and it was like, that's where I kind of realized I'm

an only child, so I, you know, can self-soothe pretty easily. But that's when I realized it was like,

okay, it's not uncomfortable to sit at a table alone or to sit at the bar by myself. I can hop on a

train, I can go see a Broadway show and just get a one way ticket. And it kind of just freed me

up to be able to still have someone to come back to, but kind of let me run around and build

that confidence. Traveling. And so then I've had some experiences. Then it became I would

travel for work and go and explore. And I think there's this misconception that it's scary or

lonely, and it's like once you get the confidence to be able to do that stuff. And I'm an extrovert,

Clearly. Um, but it allowed me to kind of build up that momentum, to be able to just say yes to

things that sounded interesting, cities that sounded fun. So really, it's probably New York City,

which is a really great place to be alone because no one's paying attention.

Theresa Stephens Exactly. And that's the thing that I've found. The more that I do it, and the

more I get comfortable traveling solo in, in whatever form, I realize that nobody cares.

Nobody's looking at me. They don't. They're not thinking about me. Everybody's involved in

their own life, you know.Molly Conner Well, and the logistics are so much easier because it's like we don't have to

agree on dates. We don't have to. Whose credit card is this going on? When do we get the

flights? What airline are we taking? It's like, just go and go have fun and figure it out along the

way. So that's kind of how I've looked at it.

Theresa Stephens Absolutely. So you and I have struck up well, we struck up a very fast

friendship. Yes. We had exchanged Instagram and posted before the night was over. Have

there been other circumstances where you've traveled solo and have met somebody new and

developed an unexpected friendship.

Molly Conner I have. It's funny. It goes against all the things we were taught when we were

little kids, right? Don't talk to strangers. But I was actually another show in Cincinnati this

summer. I was at the Avett Brothers. Um, across the river at a place called Megacorp Pavilion,

which sounds like it's out of a marvel movie, but it's the coolest venue. It's on top of a parking

garage, which is just really brilliant. But I talked to this gal next to me, Joanne. We were

actually both there with our moms, but before the concert had even started, we were Instagram

friends. We were talking about, oh, we should go to a concert. She lived in Detroit through all

this kind of chaos that's been going on in the world. We've found on social that we've been

pretty well aligned and have really struck up a friendship. So I'm looking forward to seeing a

concert, hopefully with her this summer somewhere. But like I said before, it's just an easy

place to say, what's your story? Are you a big fan? And I pretty much make a friend

everywhere I go. I went to Chicago for a Kendrick Lamar show by myself. That was the most

daunting because it was at Soldier Field and that was it was big. And of course, made friends

with some people, much like I did with you traded, you know, we took a selfie and shared it

back and forth and then, you know, it doesn't always turn into a friendship. But I've been

fortunate now, twice this just this past summer that I was able to meet you and meet this gal,

Joanne from Detroit.

Theresa Stephens That's fantastic, I love that. Do you have any more concerts planned, solo

or otherwise?

Molly Conner I do, I have, um, three this this first part of the year plan. I'm going to see a band

called The Format. Um, Nate. Nate Ruess first band. They've been broken up for twenty years.

I'm going to see them at the Ryman in April, and then I'm going to see Hayley Williams, who's

the lead singer of Paramore in Austin. That's fun because I'm going to see some friends there,

but I'm actually going to the show solo. And then in at the end of the summer, I'm going to see

Olivia Dean in Boston, which I think will be great. And then I told you a little bit about this. I'm

planning a fiftieth. My big first solo international trip is in May, and I'm going to Amsterdam and

Bruges and Paris.

Theresa Stephens Oh, unbelievable.

Molly Conner And I jokingly said to my mom, I'm sure I'll find a concert somewhere in Europe.

And then Harry styles announced he's kicking off his tour. The first two nights I'm in

Amsterdam. So? So I will be logging on to Ticketmaster at five o'clock tomorrow morning to

play the Harry Styles Hunger Games to try and get a ticket. But like we both know, it's easy toget it. Well, famous last words. We'll see how it goes, but it's easier to get a one way ticket to

those kind of things. But that's a trip that I'm really excited about because it will push me a little

further out of my comfort zone because of the language barrier. And I'm I'm pretty savvy about

getting around. But new train systems, new airports, new people, and two of the three places

I've never been. So I'm having like, I wouldn't call it anxiety necessarily, but like a lot of big

feelings about navigating that on my own, I'm excited for it. But it's like, where do I go to

dinner? How do I find a nice little bar? And I think part of that is just giving myself the

permission to get lost and then sort it out afterwards.

Theresa Stephens Oh, absolutely. So how do you, as a solo traveler, how do you plan for

that? How do you research where you want to go and and how strict would your itinerary be?

Do you plan a little a lot? Do you do like what you said? Get lost and then figure it out. What's

your process over the next couple of months?

Molly Conner So my plan is typically and I do this when I travel with my friends as well. It's like

we pick one activity. We like to start a new city with a tour just to get our bearings. I don't want

to just blow into the city and not be respectful of its history. And so like when I get to

Amsterdam, I imagine that I'll book a canal tour. Um, I did notice they have some cute wine

and cheese ones to kind of really get my my self oriented to the city and what I want to see

over the next few days. So I typically like to plan some sort of non-touristy overview of the city

if I can find one. And then I ask around for recommendations, and I like to have one firm dinner

plan, just so I have something locked in and something to look forward to. And then I sort of

take the rest of it organically. I have a note. I use the notes in my phone and anytime someone

gives me a recommendation, I add it to the list and put who recommended it. So I have that as

sort of like a little mini guidebook. But one of the things I like to do is ask my server or a

bartender where they like to go. And I find that that way I end up kind of off the beaten path a

little bit versus like, what's on Yelp.

Theresa Stephens So smart.

Molly Conner So I actually, for the first time, I'm using AI to help me plan my trip and I told it.

You know, I don't really love museums, but I like good photo ops. I don't eat seafood, but I'm a

foodie. My friends would tell you I'm not a foodie, but I like to think that I am. And it's given me

some pretty good recommendations, at least in terms of you want to be sure to hit up this

neighborhood or this place. And then I kind of just ask a lot of questions and go from there.

Theresa Stephens Oh that's fantastic, I like that. That's a new approach. Yeah. And so, you

know, one thing that I always like to ask everybody that I interview with because I think it's

something on everyone's mind, especially if they're thinking about solo travel but haven't yet

pulled the plug, which is safety strategies. Right. What kind of strategies do you use or how do

you travel differently when you are traveling alone?

Molly Conner Personally, I really prefer to stay at a hotel over like an Airbnb, only because

there's that built in safety mechanism of a front desk. Um, and sort of a line of people I, I'm not

anti Airbnb, but traveling alone, it just feels a little bit smarter. I try and do some research on

the right neighborhoods. Um, someplace like in Paris. I'm staying near a train station, so I havethat center of gravity. Um, and in the day of Uber, you just get back to where you need to go.

But I think a lot about where I'm staying, um, thinking through, like, if I had to walk back to my

hotel. What? I feel safe doing that. And then I think being careful, I try to, um, one of the things

I'm going to do a little differently this time is I'm going to delay my social posts by a day or so.

Um, just so it's not like, here's my every move. Um, and I think that we'll see. I get excited

though, and then tend to over post, but, um, and then really just being aware, I think just as

women in general, we have to do that all the time. But it's like if you, you know, maybe stop

after the second drink or read the room, sit next to someone that looks friendly at the bar and

just really not putting yourself in in vulnerable situations. But, you know, like we have to do that

every day. Really. That's true. I don't know, what have you have you found any big wins when

thinking through like how to do things safely? Maybe I could use some advice from you.

Theresa Stephens If I ever find myself in an area that I'm unfamiliar with, I always just stop.

And I've tried to tell my son this too. When he travels, just stop. Take a second, take a breath,

Orient yourself, and thank goodness we've got the technology on our phones now to kind of

figure out where we should go next or what we're doing. But don't just keep wandering. Don't

just don't look lost. Fake it till you make it is another I think big one for me is even if you're

feeling scared or unsure, it can be read and it can make you vulnerable to situations. And so

faking it. Stopping what you're doing. You know, gather yourself. Look at your phone like you

know what you're doing. Fake it until you are back in a situation that you're comfortable with.

Molly Conner Yeah, I remember being younger, back before we all had these computers in

our pockets. And this seeing this lady on the New York subway holding open a map, and I

thought, oh, you're just begging for something bad to happen to you. So I think faking it till you

make it's important. I do operate definitely in no one. No one has ever accused me of being a

type A personality. But I do feel like when I'm traveling, I take a lot of screenshots. If I find

something on the map, I, you know, just take a screenshot of it. The train route. Fortunately,

we're just in a time where we're able to kind of pregame. I really, though, have never felt

unsafe. I mean, certainly like in life I felt unsafe. But I think when you're traveling alone, it's

really empowering and it does sort of activate something in your brain that like, you're in

charge? Yes.

Theresa Stephens Absolutely.

Molly Conner Yeah. So I think just using your resources and, you know, my my dad used to

say to me when I was young, if you're going to be dumb, be smart about it.

Theresa Stephens And I like that.

Molly Conner So he may still say that now, but setting yourself up to just have a plan

generally is kind of the best thing. And you're right. Stop. If you feel you know, if your gut's

telling you something, it's very easy to change directions, especially when you're by yourself.

Theresa Stephens Exactly. And one thing I have done is that when I am in a hotel and I'm

going either to, like you were saying, going to the underground in, in London or taking a

subway somewhere or to a train station or even to a restaurant is to look at the map before Iever leave the hotel room and just getting a general idea of the direction so that I'm not

constantly looking at my phone, you know, for the next direction if I've got GPS telling me

where to go just so I can orient myself before I ever step out of the hotel. It helps. Yeah.

Molly Conner Yeah. Just planning. And then I'll do a lot of. I just keep one headphone in so

that I can have the GPS talking to me instead of having to consistently look at my phone. I

mean, sometimes it gets it wrong, but I'm not convinced that thing knows what five hundred

feet is. But it's like, oh, now turn now. But that also takes you out of that being dependent and

looking down at your phone, and lets you just be a little bit more aware of your surroundings.

Theresa Stephens Absolutely. So with all this travel that you've done to concerts or to sports

events or just going to New York, how has all these solo travel adventures affected you in your

real life? Like when you get back home and you're living your normal life, going to work, your

friendships, your relationships? How has that affected who you are?

Molly Conner That's such a great question because I think it happens. It's one of those things

that's happening where you don't know what's happening. But I do feel more confident. I really

love saying yes to things, and I have now the data to back up that it goes. Well, I also seem to

have, uh, there's a guy I work with who thinks that he always says, you're so cool. I'm like, I'm

not that cool. I just do cool things. Um, he's like, yeah, but that makes you cool. I think that just

having that confidence to do things, and whether that's taking myself out to dinner on a

Wednesday night after a bad day of work or, you know, just trying to find things that bring me

joy, I find that I know that we know that there's some chemical things that go on, those

dopamine hits that we're getting when we're doing the kind of adventures we do. Yeah. And

those just feel really nice. And so seeking those out, um, in the day to day stuff, you know, like

a pedicure would make me feel good today or let me go for a walk and get some change my

energy up. So it's just having that data that doing these things that are good for your soul really

does work.

Theresa Stephens Deciding to do it when you want to do it on your own timetable, in your real

life, day to day making those decisions to just do whatever you want to do to make yourself

happy.

Molly Conner Exactly. And it sounds so simple, but with so much negative stuff going on in the

world right now, I mean, there's a lot of joy, but there's a lot of chaos. And I think removing

yourself from that and going to seek out things that make you happy is just something that I

wish more people, and not everybody is able to do it at the scale that I'm doing it right now in

this era. But it's simple things like if you're feeling down, go get a dopamine hit, go for a walk,

go get outside, call a friend. And so it's just really sort of reprioritized the way I think about

those things and just being open to adventure, whether that's going for a drive or hopping on

an airplane.

Theresa Stephens I love that. That's absolutely right. Thank you so much for coming on

today. I really appreciate it. So great to talk to you again. We have got to plan a concert this

year at some point in time.Molly Conner And I have to tell you one of my favorite solo trips last year I, on a very wild

whim, drove down to Louisville to see Marc Maron do stand up downtown. And I just love

Louisville, so we'll have to keep an eye there, because I think it's just such a cool town. We've

got Indy, we've got Lexington, we've got Cincinnati. Um, so I think that like, there are no

accidents. So the fact that we were sitting next together at a total love fest of music and joy,

um, I mean, that guy's an alien. Absolutely. But I'm very grateful to have met you, and this has

just been such a blast. And I'm so excited about your podcast.

Theresa Stephens Thank you so much. I really appreciate that. And I feel the same about

you. It was meant to be.

Molly Conner Yes, yes indeed.

Theresa Stephens I'm Theresa Stephens and you've been listening to Roam Alone. Solo travel

shared stories.