Rhett Miller with Will Dailey

City Winery Boston presents Rhett Miller with Will Dailey live on October 27th at 7:30pm.

Rhett Miller has spent three decades sharpening hooks that feel effortless and hitting hardest live, and a solo set strips that songcraft down to its rawest form. Best known for fronting Old 97's, recently honored with a Lifetime Achievement Award at the Americana Awards, Miller brings the same restless wit and melodic instinct to his own catalog, most recently 2025's A Lifetime of Riding by Night. Expect a night of sharp, story-driven songwriting from a genuine road veteran, delivered with the kind of warmth and humor that comes from decades of knowing exactly how to hold a room. In a seated house this close, every lyric and aside lands the way it's meant to. Settle in with a glass of something good, let the night unfold at its own pace, and watch a masterful songwriter work a room built for exactly this.

When not on tour, Rhett Miller resides in New Paltz, New York with his wife Erica and their two children. He can be followed on Instagram, Facebook and X (@rhettmiller). Information about his solo music projects can be found at www.rhettmiller.com, while information about Old 97’s can be found at www.old97s.com.

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Will Dailey makes emotionally honest American indie rock for people who value connection over noise. Rooted in American songwriting tradition but accountable to the present, his work explores how we talk, how we don’t, and what it costs either way. These are not songs chasing relevance or speed, they’re built for resonance, designed to age with the listener rather than spike in the moment.

Across seven albums, Dailey has built a career defined less by scale than by trust. His music treats listening as an act of care and the audience as partners in a long conversation. Albums functioning as chapters rather than content drops. Vulnerability here isn’t exposure; it’s craft.

The songs don’t offer easy answers, but they stay with the questions long enough for something honest to surface. Dailey’s approach to innovation mirrors his songwriting: deliberate, restrained, and human. Projects like The $10 Song —a one-time listening experience shared through a traveling Discman and handwritten journal—use limitation not as a stunt, but as a boundary. Scarcity becomes a way to restore value, ritual replaces noise, and technology is used intentionally rather than obediently.

Independence for Dailey is not isolation, but alignment. After stepping away from the major-label system, he reframed artist sovereignty as responsibility: protecting the work, the listener, and the relationship between them. Trust replaces scale as the core currency. These ethical practices have brought him on stage and studio with Eddie Vedder, Bruce Springsteen, Willie Nelson, Roger McGuinn, Steve Earle, Brandi Carlile, and T Bone Burnett; appearances on more than 50 television shows and films; performances at Farm Aid four times.

Often described as a Venn diagram of multiple genres with a rich vintage feel, Dailey’s music resists nostalgia as comfort. Instead, it interrogates the past, asking what made listening sacred and how to protect that now. His songs frequently act as proxies for conversations men weren’t taught to have, making room for tenderness without apology and honoring communication as an act of courage.

This is music that stays—long after the moment passes, long after the platforms change.

Dine At Your Show（新しいタブで開きます）

🍽️ We provide food and beverage service directly to your table in the venue. Or, for an expanded menu and more relaxed experience, arrive early and enjoy a meal in our restaurant before the show. When dining in the restaurant, reservations are encouraged and can be made via Resy starting one month before the show. View Our Concert Dining Menu.（新しいタブで開きます）

Wine At Your Table（新しいタブで開きます）

Reserve your preferred wine by filling out this form（新しいタブで開きます） and have a bottle waiting at your table when you arrive at your show. No more waiting for your first drink! We will save your wine preference and have a bottle at your table for all future shows. When you want to change your wine, come back to this form and update your preference.

2 Item Per Person Encouraged

🎶 While we do not require a two-item food or beverage minimum, we strongly encourage it. Most ticket revenue goes directly to the artist and production costs, so food and drink purchases help support the staff, service, and atmosphere that make these intimate shows possible.

The good news: we think you’ll love the food and wine just as much as the show.

Become a Vinofile Member（新しいタブで開きます）

🍷 Members get 48 hour early access to new shows, pay no ticket fees, and earn points to exchange for complimentary tickets. Vinofile VIP+ members also receive many wine benefits. Add a membership to your cart during checkout to start saving now. Already a member? Make sure you are signed in to access your benefits. Become a Vinofile Member and enjoy the benefits today.（新しいタブで開きます）