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!

Commission a Piece

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For Sale

Pittsburgh

plein air

still life

Toronto

5x7 in Prints (various options)

Ink, Acrylic, Alcohol Marker

Prints from $10

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

Popular

Tazza D'oro - Pittsburgh, PA Illustration

2025

Ink, Alcohol Marker

Prints 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

2025

Ink, Alcohol Marker

Prints from $10

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

Brillobox (Bloomfield / Lower Lawrenceville)

2026

watercolor

Original $125

Buy

Thunderbird Café & Music Hall

2026

ink

Original $250

Prints from $10

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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

2026

ink and alcohol marker on cold pressed paper

Original $200 · Sold

Prints from $35

Buy

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

Titty Sphinx (Allegheny Cemetery)

2026

ink on tan toned paper

Prints from $10

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Sold

PNC Park — Watercolor

Watercolor

Original $200 · Sold

Sold out

Sold

PNC Park — Ballpoint Mini

Ballpoint pen

Original $100 · Sold

Sold out

Highland Park Fountain, Pittsburgh, PA

2026

ink and alcohol marker on cold pressed paper

Original $150 · Sold

Prints from $10

Buy

Rialto Street, Troy Hill, Pittsburgh

2026

Ink

Original $150 · Sold

Prints from $40

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sketch of pittsburgh skyline and bridge from north shore

Pittsburgh Skyline from North Shore

2026

Ink

Original $200

Prints from $10

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Mr. Blue - Harley Davidson Motorcycle

2026

Ink, Alcohol Marker

Iron City Clock - Southside, Pittsburgh, PA

2026

Ink & Marker

Original $150 · Sold

Prints from $40

Buy

Sold

Kaibur 2 - Polish Hill, Pittsburgh, PA

2026

Ink Pen

Original $150 · Sold

Sold out

Sold

Three Phase Pole

2026

Ink, Acrylic, Alcohol Marker

Original $100 · Sold

Sold out

West Penn Rec Center - Polish Hill, Pittsburgh, PA

2026

Watercolor on Cold Pressed Paper

Original $250

Buy

Rock Room - Polish Hill, Pittsburgh, PA

2026

Ink, Alcohol Marker

Original $150 · Sold

Prints from $40

Buy

Framed original ink drawing of the Pittsburgh skyline from Fineview

Fine View of PGH

2026

Ink

Original $125

Buy

Framed original ink drawing of St. Stanislaus Kostka Catholic Church

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

2026

Ink

Original $125

Buy

Jean-Marc Chatellier - Millvale, Pittsburgh, PA

2026

Ink, Acrylic, Alcohol Marker

Original $200 · Sold

Prints from $35

Buy

Sold

The Tunnel at Highland Park, Pittsburgh, PA

2026

Ink on cold pressed paper

Original $100 · Sold

Sold out

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

2026

Ink

Original $150 · Sold

Prints from $10

Buy

Apple

2026

Ink, Acrylic, Alcohol Marker

16th St Bridge, Pittsburgh, PA

2026

Ink & Marker

Original $100

Prints from $10

Buy

sketch of beer and hotdog on tan toned paper

Kennywood Dog and OG Beer

2026

Ink, Acrylic, Alcohol Marker

Original $100 · Sold

Prints from $10

Buy

Popular

Heinz Ketchup Bottle

2026

Ink & Marker

Original $100 · Sold

Prints from $40

Buy

Quarter Orange

2026

Acrylic Marker

Bananas

2026

Ink, Acrylic, Alcohol Marker

Original $100 · Sold

Prints from $10

Buy

Tea Getting Cold

2026

Ink, Acrylic, Alcohol

Toast with Peanut Butter and Blueberries

2026

Ink, Acrylic, Alcohol

Highland Park Houses, Pittsburgh, PA

2026

Ink, Alcohol Marker

Original $200 · Sold

Prints from $10

Buy

Kaibur Coffee - Polish Hill, Pittsburgh, PA

2026

Ink, Alcohol Marker

Original $200 · Sold

Prints from $30

Buy

Row House Cinema - Lawrenceville, Pittsburgh, PA

2025

Ink, Alcohol Marker

Prints from $30

Buy

Mr. Smalls Theater - Millvale, Pittsburgh, PA

2025

Ink, Alcohol Marker

Prints from $30

Buy

Biddles Escape - Pittsburgh, PA

2025

Ink, Alcohol Marker

Prints from $30

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Coffee Tree - Dormont, Pittsburgh, PA

2025

Ink, Alcohol Marker

Prints from $30

Buy

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

Bryant Street Market - Pittsburgh, PA

2025

Ink, Alcohol Marker

Prints from $30

Buy

Bryant Street House, Pittsburgh, PA

2025

Ink, Alcohol Marker

Christi Pitts Park 1 - Toronto, Ontario, CA

2025

Ink, Alcohol Marker

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

2025

Ink, Alcohol Marker

Original $100

Buy

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

Trinity Bellwoods Park - Toronto, ON, CA

2025

Ink, Alcohol Marker

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

2025

Ink, Alcohol Marker

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.