Painting San Francisco Streets

Well I never thought I’d want to paint a city street but San Francisco changed my mind. The subject of the painting is really the light and atmosphere and the interesting shapes found in a street scene.

This workshop also explores how you can free up your colours by working from a black and white photograph, and how we can use images from the internet to paint from. Enjoy!

"San Francisco" 14x14" Oil on Canvas by Richard Robinson

Welcome to our "Streets" painting workshop, where we’ll explore the dynamic beauty of San Francisco’s iconic cityscapes. I’ll admit, I never thought I would be drawn to painting urban streets, but there’s something magical about the glow of light streaming down a busy avenue, the interplay of shadows cast by tall buildings, and the charm of a cable car rumbling along its tracks.

In this workshop, we’ll focus on capturing the atmosphere, light, and unique shapes that make a street scene come alive, while also learning how to free up our colour choices by starting with a black-and-white reference image.

Whether you follow along with me step-by-step or take inspiration to create your own unique composition, this lesson is all about experimenting, learning, and having fun.

We start by cropping the scene to include only those elements neccesary to spell out the scene. The cable car is brought in from another photo and the light reimagined upon it. Then, by working from a black-and-white photograph, we’ll concentrate on establishing the values first — the lightest lights, darkest darks, and all the mid-tones in between.

This approach helps simplify the scene and ensures that our painting has a solid foundation. Remember, values are the backbone of any successful painting, and getting them right early on will make the rest of the process much easier. 

Once the values are in place, we’ll start building colour, and here’s where the real fun begins. Without being tied to the colours in the original reference, we’ll have the freedom to invent and exagerate hues, playing with colour temperature to create mood and interest. 

By exagerating the atmospheric perspective in the background we can create more drama and interest, creating a soft backdrop that enhances the centre of interest rather than competing with it.

The key to that is first choosing the colour of the light, in this case a warm yellow, and mixing all the colours in the background closer to the colour of the light.

As we move towards the finishing touches, we’ll refine the details, adding texture and small highlights to bring the scene to life. Whether it’s the gleam of sunlight on a cable car or the subtle texture of the road, these final touches can make all the difference.

This is an exercise in taking inspiration from a photo while transforming it into something uniquely your own.

Painting city streets might feel ILIKE a challenge at first, but it’s also an incredibly rewarding subject to explore. You’ll develop your skills in creating atmosphere, managing values, and playing with colour in ways that can open up new possibilities in your art.

So grab your brushes, pick your favourite medium, and let’s bring the streets of San Francisco to life on your canvas. Remember, the most important part of this process is to enjoy yourself and embrace the journey. Happy painting!

Student Critiques

Here are some of the student paintings from this workshop, along with my critiques.

12" x 12" oil on canvas by Jeff Danzik

Strong work, Jeff. Good drawing and an eye for keeping the large value masses clear and not over complicated - putting the detail where it counts. If you layered over the light shapes in the road again and sharpened up the cast shadow edges you'd get a better sense of strong sunlight there. Intensifying the light and colour on the right side of the cable car would help with that too - accentuating the centre of interest. The greens leading up the street should grey down as they recede. Overall, great job!

"STREETS OF SAN FRANCISCO" watercolour & gouache by Eric Hillmer, Toronto, ON, Canada.

Very vibrant and energetic, Eric - it draws my attention. You’ve captured the bustling atmosphere beautifully with the bold use of color and strong shapes—particularly the lively greens of the tree constrasting the punchy red of the streetcar. Your composition draws the viewer right into the scene, leading them up the hill and into the distance.

If you'd gone a little lighter in value in the buildings in the top right of the street that would have created even more depth. When painting trees, try to avoid patterns of same sized splotches. A stronger design is achieved by building a tree with larger organic light and dark shapes, then adding some variety of smaller details in and around those base shapes. You're nearly there with this one. Great work overall, and I can see so much personality in this piece—keep it up!

Street Scape by Paul Seymour

This is a lovely depiction of a quaint street scene. The warm tones and direct light on the building facades create a welcoming atmosphere, and the sky is beautifully rendered with its dynamic cloud shapes and subtle colors contrasting the angular structures below. You've captured an inviting sense of place, which is so important in street scenes, although this could be aided by including more life on the street - vehicles and people.

Another element you could add to release the boxed-in feeling of the street is to create a haze of light spilling over the furthest buildings, coming from the right, pushing them further back in space and inviting the view to walk around that corner into the light. At present, all the dark values back there are the same as the dark values in the foreground, which flattens the image. Adding atmospheric perspective could be the next step up the ladder for you. This could be achieved in this painting with light glazes, but the effect is generally more effective and colourful when planned and executed in the first layers. You're doing great—keep pushing forward, Paul! I’m excited to see your next painting.

If you're going to San Francisco, don't forget to wear some flowers in your hair.

Artist: Anne-Dore Leisering

This is a beautifully atmospheric piece! I love how the soft haze envelops the city, creating a sense of distance and mood. To have that cablecar really pop you could lighten the street around it and sharpen up the edges, and it also needs that strip of light on the road to its right to make more sense of the light there - indicating a gap between the buildings letting in a shaft of light - that perfect moment where the cable car emerges from the shadows into the light.

Your powerpoles are making a 1,2,3,4 pattern, which for the sake of variety is to be avoided generally, which you can do by removing the second or third pole. They also need to get much thinner as they recede. I hope that helps. You’re doing some lovely work here. Keep it up!

Streets 9 1/2" x 10 1/2"Acrylic on canvas by Karen Woodhouse

Hi Karen, you've done a great job of the soft atmospheric perspective in the background, being careful to avoid and dark values that would have spoiled the illusion of depth. You're drawing is solid too, with the perspective of the street well handled, though the cars could do with a little tweaking, namely making them bigger, and the cablecar as well. Wonderful work overall—this is a tricky subject, and you've done a great job capturing its charm! Keep it up!

Congratulations and thanks to everyone who entered a painting into the workshop. Great work!

Get the full lesson here: https://mypaintingclub.com/lessons/8-Streets

- Richard.