Welcome back to Shecky's Jam Bands. I'm Shecky,
and today we're doing something a little different.
Every episode of this show we talk about bands
you may already know, legends with decades of
history, Hall of Fame moments, farewell tours,
reunion shows, the whole arc. But live music
doesn't just belong to the bands that have already
arrived. It also belongs to the bands that are
in the middle of the journey right now. The ones
who are still playing club shows, still building
their sound, still earning every room they walk
into. Today's band is one of those. Today we're
talking about Roundtrip. Four musicians out of
Boston, Massachusetts who set out on a mission
that is stated right on their website. Plain
as day. They are determined to take you there
and back. I love that. Determined. not hoping
to, not aiming to, determined. That's a band
that knows where they're going. Let's get on
board. Round trip is Jake Stevenson on guitar
and vocals, Chris Cooper on keyboards, Drake
Milhousen on bass, and Walker McMillan on drums.
Four people, four instruments, one city, Boston,
Massachusetts. Now, Boston has one of the richest
and most underappreciated jam and indie music
scenes in the country. It's a college town at
heart, more colleges and universities per square
mile than almost anywhere in the U .S. And that
means a constant influx of young musicians who
are serious about their craft, who have studied
theory, who have been sitting at clubs and open
mics since they were teenagers. The music that
comes out of Boston tends to be thoughtful. It
tends to have structure and freedom. It tends
to care about both the song and improvisation
within that song. That is exactly what Roundtrip
brings to the table. The band describes their
sound as blending diverse songwriting and powerful
riffs with experimental improvisation. They call
themselves versatile and exploratory. They describe
their mission as taking onlookers under their
sonic wing and inviting any and all to take the
journey with them. That is the language of a
band that genuinely believes in what music can
do for people in the room, not just for the band
themselves. They built their sound on the reputation
the way you're supposed to by playing Boston
clubs, college venues, regional shows, opening
slots for bands that were further along in their
journeys. They've shared stages with Dogs in
a Pile, High Fade, and Neighbor, three of the
most exciting acts in the modern jam scene. They
played the Northlands Music Festival in New Hampshire,
one of the best regional jam band festivals in
the Northeast. Every single one of those shows
was another deposit in the trust account they're
building with their audience. Round trip. Two
words contain entire philosophy about the music,
if you let them. A round trip, by definition,
takes you somewhere and brings you back. You
leave from one place, you travel somewhere new,
maybe somewhere surprising, maybe somewhere disorienting,
maybe somewhere transcendent, and then you return,
changed, expanded. You're back where you started,
but you're not the same person who left. That
is exactly what a great jam band show is supposed
to do. You walk into the venue, you know a few
of the songs, or none of them. The band starts
playing the music, moves through different terrain,
structured songs opening into improvised sections.
Those sections taking unexpected turns, landing
back on the melody, lifting off again. And when
you walk out, two hours later, you're back in
the parking lot, but something has shifted. You
went somewhere. You came back. Roundtrip. The
band puts it on their homepage in the most direct
possible terms. Roundtrip is a progressive jam
band determined to take you there and back. Not
just take you there, there and back. The full
journey. That commitment to returning the listener
to a place of resolution, giving the improvisation
a landing strip. is one of the things that separates
good jam bands from great ones. Roundtrip has
thought about this. The name is not accidental.
Roundtrip released their first EP titled Break
Failure before going bigger. Break Failure, as
a companion piece to the band name Roundtrip,
that title is doing a lot of work. You're on
a round trip, but what if the brakes fail? What
if the journey doesn't stop when you expect it
to? What if the music keeps on going, keeps pushing,
keeps building past the point where you thought
it would resolve? That's not an accident either.
This is a band that thinks about what their music
means and how to signal it to listeners before
the first note even plays. Their self -titled
debut album followed in December 2023 and it's
where I want to point new listeners. The debut
album is the fullest picture of what roundtrip
is capable of. Diverse songwriting that moves
between styles without ever losing that groove.
Powerful riffs that give the improvisational
sections something to push against and a keyboard
presence from Christopher Cooper that gives the
band a textural range you don't always find in
a four -piece jam configuration. Now, every band
has a show, a specific performance where all
of the work they put in The rehearsals, the small
club gigs, the nights of playing for 20 people
who weren't really paying attention suddenly
pays off in a single concentrated burst of music
that makes everyone in the room understand that
this band has arrived. For Roundtrip, the Northland
Music Festival represents exactly that kind of
milestone. The Northland's Music and Art Festival
in New Hampshire has quickly become one of the
most beloved regional jam festivals in the Northeast.
The kind of festival that books headliners like
The String Cheese Incident, Mike Gordon, and
Twiddle, while also carving out space for the
next generation artists who are still working
their way up. Getting a slot at Northlands is
not nothing. It means the festival is paying
attention. It means the regional booking community
is paying attention. When Roundtrip walked onto
the festival stage, They were playing for a crowd
that might not have known a single song they
played. Festival audiences are different from
club audiences. Club audiences, even small ones,
tend to be there specifically for you. Festival
audiences contain hundreds of people who are
just passing through, wandering between stages,
looking for something to stop them in their tracks.
What Roundtrip did at Northlands was stop them
in their tracks. They brought the energy, the
riffs, the improvisation, all of it. Songs opened
up in ways that casual listeners couldn't perfectly
predict, and that unpredictability is exactly
what festival crowds responded to. When a band
you've never heard of takes a musical left turn
that makes you grab the shoulder of the person
next to you and say, wait, what just happened?
That is the moment. That is how you earn a new
fan. in a festival setting, not by being safe,
by being willing. Roundtrip was willing and the
people who caught their Northlands set left with
a new name to remember and a reason to look forward
to the next show. That's the Roundtrip story
right now. Not a legend yet. In the middle of
becoming one, every night out there, there's
another chapter. Here's what I want to leave
you with about Roundtrip. The jam world right
now is one of the most exciting periods in decades.
There's a new generation of bands, Dogs in a
Pile, High Fade, Goose, Great Blue, and yes,
Round Trip that grew up listening to Fish and
String Cheese Incident and STS -9 and Railroad
Earth and all the bands we've been covering in
this podcast. And they are carrying the tradition
forward with their own voices. They are not imitating
what came before, they are adding to it. Roundtrip
is Boston's contribution to that conversation.
For musicians who believe deeply enough in the
Roundtrip, in taking you somewhere and bringing
you home, to put it right at the center of everything
they do, the name, the mission, and the music.
Find the Break Failure EP, find the debut album,
check their website out. roundtripband .com for
new show dates. And if they're playing anywhere
near you, in Boston, in the Northeast, at a festival
this summer, go. Pay the $12 at the door, stand
in the room, take the road trip. That's Road
Trip. That's Shecky's Jam Bands. Thank you for
listening, and I'll see you on in the next episode.