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Will Dailey

@willdaileyofficial

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You found me. I don’t know how but you found me. On the road all fall. Boys Talking is out.

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#bostonmusicscene #denstock #localmusic #bostonmusic #wbznewsradio

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I’ll admit it: I miss the “good old days” when physical music packaging was part of the experience.

There was something special about opening an LP, 45s or CD for the first time. Studying the cover. Reading the liner notes and lyrics. Discovering who played what, where it was recorded, and who helped bring it to life. Finding a detail tucked inside that made you look again.
The packaging offered a glimpse into the people behind the music. The photography, typography, illustration, and overall art direction became another way to enter their world—not just a small thumbnail accompanying a play button. As a songwriter, musician, designer, and art director, I’ve always valued that connection between what we hear and what we see. Thoughtful music packaging can extend the mood, reveal another layer of the story, or create an unexpected contrast that makes the listening experience richer.
I’ve always felt that my job was to create the visual complement to a record. Not to explain every song or compete with the music, but to give it a physical presence—something you could hold, explore, revisit, and make your own.
I’m grateful for the convenience of streaming. But I still love the ritual of putting on a record, opening the sleeve, and giving both the music and the artwork my full attention.

Here are a few of my favorite releases I’ve designed or art directed over the years. Big props to @ryanfreasecreative, @irafcummings, and @mhkaiser for their creative contributions with these releases.

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Two nights at 118 this weekend!

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Love me some Will Dailey (@willdaileyofficial)! 🥰🎸🎶✨

“My Old Ride” off of his latest album, BOYS TALKING

Saturday, 10/17/2026 at @thewonderbarofficial

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@willdaileyofficial with an always impressive set. He opened for Paula Cole last month at @the_wilbur 9.18.2026 #WillDailey #Singersongwriter #BostonMusic

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A little look into Will Dailey's (@willdaileyofficial) 909 Session 👀🎸

The Boston-based singer-songwriter brought his thoughtful lyrics, soulful vocals and unmistakable indie-rock spirit to The Living Room to chat with Jon Hart where they talked humble beginnings, chance encounters and the realities of working in music among the digital age.

👉 Listen to the live session now online and be sure to subscribe on YouTube to be the first to see his full performances when they drop! Link in bio.

📸 John McGrath - @johng.mcgrath

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@willdaileyofficial performing live in Boston • June 3, 2026

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thank you @matthewreid for the absoluteee plug on Mix 104.1 Acoustic Sunrise + for spinning Wired 🥹♡

the plot has been moving fast lately 🤘🏻
singing with O.A.R., KT Tunstall + Gavin DeGraw’s band → releasing my FIRST EVER music video for Wired → and now being nominated for 4 New England Music Awards 🫠

ANDDD the band + I are performing at the award show 👀

girl what is going ON ✿ 😂 you can vote once every day in all 4 categories ♡

And once again, and if you’re not already listening to Mix 104, this is your sign to tune in + support the station that’s been showing so much love to local artists ♡✿

#Boston #mix104 @mix1041 @theacousticsunrise

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Big month in Philly for the John Pronto Band! We’ll be at 118 North with Will Dailey on October 18th
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#phillymusic #118 pronto

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Will Dailey #folk

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Tomorrow!! Performing with @willdaileyofficial at @northside_social

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Life on the road 🚙 😍🎵

For the past 2 weeks I’ve been on the road with the magical Paula Cole, having the time of my life 💗🎵 I am beyond grateful to be travelling with such talented, kind, and wonderful humans….so far we’ve played New York, Boston MA, Kent OH, Chicago IL, Bourbon & Beyond Fest, Fairfield CT and Woodstock NY 🎵

Tonight: Denver! 🏔️ 💫

Hope we will see YOU somewhere soon!! ✈️

#paulacole #touring #livemusic #femaledrummer

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