Art That Celebrates Main Street Pittsburgh

Cassandra Wilcox · Pittsburgh-based Sketch Artist

Hand-drawn originals and prints of the landmarks and main-street spots that make Pittsburgh feel like home. Featuring neighborhoods from Highland Park and Millvale, to Lawrenceville and Polish Hill, South Side, and North Side among others!

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Cicero

Pittsburgh

plein air

still life

Toronto

Sketch of Tazza D'oro Coffee Shop in the Highland Park neighborhood of Pittsburgh, PA

Popular

Tazza D'oro - Pittsburgh, PA Illustration

Ink, Alcohol Marker · 2025

From $10

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Ink and Alcohol Marker Sketch of Park Place Pub in the Highland Park neighborhood of Pittsburgh, PA

Park Place Pub - Pittsburgh, PA Illustration

Ink, Alcohol Marker · 2025

From $8

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Framed original watercolor of Alexander's Ice Cream, a small ice cream shop in Cicero, Indiana, hanging on a wall

Alexander's Ice Cream (Cicero, IN)

watercolor · 2026

Original $75

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William Penn Tavern

ballpoint pen in various colors, with acrylic marker

From $10

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Cathedral of Learning

watercolor · 2026

Original $125

From $35

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Framed original watercolor of Brillobox, a music venue in Bloomfield, Pittsburgh

Brillobox (Bloomfield / Lower Lawrenceville)

watercolor · 2026

Original $125

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Thunderbird Café & Music Hall

ink · 2026

Original $250

From $8

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Framed original ink drawing of Max's Allegheny Tavern, the German tavern in Pittsburgh's Deutschtown / North Side

Max's Allegheny Tavern - North Side

ink and alcohol marker on cold pressed paper · 2026

Original $200 · Sold

From $8

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5×7 art print of the Allegheny Cemetery sphinx statue, Pittsburgh

Titty Sphinx (Allegheny Cemetery)

ink on tan toned paper · 2026

From $8

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PNC Park (Watercolor)

Watercolor

Original $200 · Sold

From $40

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PNC Park (Ballpoint Mini)

Ballpoint pen

Original $100 · Sold

From $8

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Highland Park Fountain, Pittsburgh, PA

ink and alcohol marker on cold pressed paper · 2026

Original $150 · Sold

From $10

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Rialto Street, Troy Hill, Pittsburgh

Ink · 2026

Original $150 · Sold

From $8

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sketch of pittsburgh skyline and bridge from north shore

Pittsburgh Skyline from North Shore

Ink · 2026

Original $200

From $8

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Mr. Blue - Harley Davidson Motorcycle

Ink, Alcohol Marker · 2026

Iron City Clock - Southside, Pittsburgh, PA

Ink & Marker · 2026

Original $150 · Sold

From $8

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Sold

Kaibur 2 - Polish Hill, Pittsburgh, PA

Ink Pen · 2026

Original $150 · Sold

Sold out

Sold

Three Phase Pole

Ink, Acrylic, Alcohol Marker · 2026

Original $100 · Sold

Sold out

West Penn Rec Center - Polish Hill, Pittsburgh, PA

Watercolor on Cold Pressed Paper · 2026

Original $250

Buy

Rock Room - Polish Hill, Pittsburgh, PA

Ink, Alcohol Marker · 2026

Original $150 · Sold

From $8

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Framed original ink drawing of the Pittsburgh skyline from Fineview

Fine View of PGH

Ink · 2026

Original $125

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Framed original ink drawing of St. Stanislaus Kostka Catholic Church

St. Stanislaus Kostka Catholic Church - Strip District, Pittsburgh, PA

Ink · 2026

Original $125

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Jean-Marc Chatellier - Millvale, Pittsburgh, PA

Ink, Acrylic, Alcohol Marker · 2026

Original $200 · Sold

From $35

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Sold

The Tunnel at Highland Park, Pittsburgh, PA

Ink on cold pressed paper · 2026

Original $100 · Sold

Sold out

“Dippy” the Dino - Carnegie Museum, Pittsburgh, PA,

Ink · 2026

Original $150 · Sold

From $8

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Apple

Ink, Acrylic, Alcohol Marker · 2026

16th St Bridge, Pittsburgh, PA

Ink & Marker · 2026

Original $100

From $8

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sketch of beer and hotdog on tan toned paper

Kennywood Dog and OG Beer

Ink, Acrylic, Alcohol Marker · 2026

Original $100 · Sold

From $8

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Popular

Heinz Ketchup Bottle

Ink & Marker · 2026

Original $100 · Sold

From $8

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Quarter Orange

Acrylic Marker · 2026

Bananas

Ink, Acrylic, Alcohol Marker · 2026

Original $100 · Sold

From $10

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Tea Getting Cold

Ink, Acrylic, Alcohol · 2026

Toast with Peanut Butter and Blueberries

Ink, Acrylic, Alcohol · 2026

Highland Park Houses, Pittsburgh, PA

Ink, Alcohol Marker · 2026

Original $200 · Sold

From $10

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Kaibur Coffee - Polish Hill, Pittsburgh, PA

Ink, Alcohol Marker · 2026

Original $200 · Sold

From $10

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Row House Cinema - Lawrenceville, Pittsburgh, PA

Ink, Alcohol Marker · 2025

From $30

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Mr. Smalls Theater - Millvale, Pittsburgh, PA

Ink, Alcohol Marker · 2025

From $8

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Biddles Escape - Pittsburgh, PA

Ink, Alcohol Marker · 2025

From $10

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Coffee Tree - Dormont, Pittsburgh, PA

Ink, Alcohol Marker · 2025

From $30

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Ink and alochol marker drawing of Bryant Street Market in the Highland Park neighborhood of Pittsburgh, PA

Bryant Street Market - Pittsburgh, PA

Ink, Alcohol Marker · 2025

From $10

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Bryant Street House, Pittsburgh, PA

Ink, Alcohol Marker · 2025

Christi Pitts Park 1 - Toronto, Ontario, CA

Ink, Alcohol Marker · 2025

Original $100

Buy

pink, purple-blue, and warm grey sketch of tree next to bench at Christi Pitts Park in Toronto, Ontario, Canada

Christi Pitts Park 2 - Toronto, ON, CA

Ink, Alcohol Marker · 2025

Original $100

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Ink sketch of bare trees along a warm grey path with pink grass on both sides.

Trinity Bellwoods Park - Toronto, ON, CA

Ink, Alcohol Marker · 2025

Original $100

Buy

some guy on a laptop at wanda's pie in the sky

Wanda's Pie in the Sky - Kensington Market, Toronto, ON, CA

Ink, Alcohol Marker · 2025

About Cassandra

Cassandra Wilcox is a Pittsburgh artist drawn to the things that make this city itself: the corner storefronts, the neon signs, the row houses climbing the hillsides of Polish Hill and the South Side Slopes. Neighborhood by neighborhood, she draws the landmarks and everyday details locals recognize in their bones. She sells original artwork and prints here, takes custom commissions, and shows her work at markets around Pittsburgh. Follow along on Instagram at @casswilcoxart.