Illustrated Love Letter to Indianapolis

Sometimes a city finds its way into your sketchbook — not because of a client brief or a deadline, but because you can’t stop noticing its patterns.

This one began as a quiet study of home — the landmarks, textures, and stories that make Indianapolis, well, Indianapolis. The L.S. Ayres clock, forever marking time above Washington Street. The bold form of Lucas Oil Stadium. The Ruins at Holliday Park, that perfect mix of crumbling beauty and green quiet. And somewhere between a plate-sized tenderloin and a slice of sugar cream pie, a wink to Sammy Terry — because every city deserves a bit of local legend.

Each landmark is drawn with the same rhythm and care I bring to my other illustrated cities: linework that balances architectural precision with a bit of looseness, curiosity, and humor. It’s a way of honoring place without over-explaining it.

At the heart of it all sits that bold “Indianapolis” across the center — a nod to vintage racing pennants and hand-painted signage. It’s confident, a little nostalgic, and feels right at home surrounded by the city’s most iconic shapes.

Drawing Cities as Stories

Cities are layered personalities — part history, part folklore, part everyday detail you only notice when you pause. Illustrating them isn’t just about drawing buildings; it’s about capturing the feeling of belonging somewhere.

When I draw a city, I’m less interested in perfect accuracy and more in capturing tone — how memory clings to place. Each illustration turns into a story about place, told through rhythm, line, and color.

Why Indianapolis

Because it’s unpretentious. Because it’s a little weird and endlessly genuine. This illustration is my love letter to Indy — layered, imperfect, and full of affection for the place that built my sense of design, storytelling, and belonging.

So tell me — what’s your favorite Indy landmark? Reach out if your city, venue, or destination deserves its own moment in line art.


Got a custom map or venue project?

Vacation rental hosts, boutique hotels, and Airbnb dreamers — my sketchbook is open. Give me a shout!

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A Little Paper, A Lot of Hospitality