Strada challenge September 2026

In September this year, I completed the Strada Challenge for the first time.

I’ve been struggling to produce much work in 2026 and so I wanted to do something to get me creating again. As the challenge involved painting or drawing from life every day throughout September I thought it would be ideal. Plus, at the end of the month there was a draw to win an easel (I didn’t win!)

Over the course of the month, I did 7 ink sketches, 17 Inktense pencil sketches and 7 acrylic paintings. Looking back over my efforts, it’s certainly true that some days were better than others but overall it was a really good experience. Here are some of the highlights for me:

Day 2 - Yaverland Beach

This is acrylic and half a ton of sand on A4 paper!

I drove to Yaverland beach with the intention of painting Culver Cliff but it was too windy to use my easel. I had to kneel down and balance my painting board on a bit of old brick and it felt like I spent more time battling the sand than painting! This is definitely one of those situations when the experience was more memorable than the end result and it’s also true that I would not have done this if I wasn’t taking part in the challenge.

Day 4 - Sculpture by the Lakes

This is the first painting I did on the day. It's acrylic on A4 paper

This is the second painting. It's A3 and was dashed off in less than an hour

This was a long day. I got up at 4:00am to travel from the Isle of Wight to Sculpture by the Lakes near Dorchester for a plein air painting day organised by Jackson's Art Supplies. I managed to get two paintings completed and it was a lot of fun. I think it’s the first time I’ve painted silver birch trees (though no sculptures or lakes!)

Day 9 - Seaview

I used fine liner pens for this sketch

I met a friend at Seaview and we sat on the beach drinking coffee and sketching the iconic Seaview tree. I plan to do a “proper” painting of this view in the future and so this was good practice and a great way of spending an afternoon.

Day 10 - Osborne House

This is acrylic on A4 paper. I wanted to let some of the orange underpainting show through

I painted on the beach at Osborne House. This involved lugging my equipment 1.2 kilometres down a hill to the beach but the experience made it worthwhile. (I really need to reduce the amount of stuff I take with me!)

On the way back I was stopped by someone who wanted to look at my painting and their verdict was “well at least you enjoyed yourself painting it”, which I found really amusing

Day 12 - Sandown Beach

I started by using the pencils to create a watercolour-style wash and then drew over the colours to create texture and (hopefully) a sense of energy.

It was another breezy day so I sat on the beach and used Inktense pencils to sketch the scene. I did a few Inktense sketches over the course of the month because they are really portable and versatile and I had a lot of fun experimenting with them.

Day 14 - On the cycle path towards Alverstone

I used fine liner pens in my sketchbook and it was only afterwards that I realised I'd missed out one of the trees

This sketch was done sat by the side of the cycle path between Sandown and Alverstone. It’s a path that I’ve walked down many times before. It was threatening rain most of the time and I was accompanied by some rather loud ducks!

Day 20 - Blackgang Viewpoint

Originally I had planned to go over this sketch with pencil lines, like I did before but I ran out of time

Another Inktense sketch; this time of the viewpoint at Blackgang. From there you can see across to the western tip of the island. It was a beautiful sunny day - one of those times when you can’t imagine there being any better way of spending the morning.

Day 26 - Cranborne Lodge workshop with Kim Day

Acrylic on A4 paper. I was definitely thinking of Kim's style!

My first award!

Another early start and trip to the mainland and this time it was for a workshop at Cranborne Lodge in Dorset with Kim Day – the winner of Landscape Artist of the Year 2026. 

It was great to meet Kim; she had loads of really good advice and was very generous with her time to everyone taking part in the day. Even better, I won a prize for my painting! So, I guess I’m award winning now?

Day 27 - Los Altos Park, Sandown

Intense pencils in my sketchbook. I was trying not to get them wet!

I was in the local park for this sketch and it rained, so it’s my first time sketching from under an umbrella!   

Day 30 - The Pepperpot

The "Pepperpot", which, needless to say, I didn't draw

The last day of the challenge! I felt I should go somewhere memorable so I climbed up to the Pepperpot, (which is one of the highest points on the island), for my final sketch of the month. There are wonderful views in all directions and it seemed like a suitable way of ending the challenge.

Inktense pencils in my sketchbook. Essentially I had my back to the Pepperpot when I did this sketch.

So would I do the challenge again?

I learnt quite a lot over the course of the month.

Before September I’d barely been out painting or sketching on my own. I’d expected to spend a lot of time inside sketching “interesting vegetables” but the weather was really quite good and so I went outside every day.

Who’d have thought that painting and sketching outside is fun!

Initially I wondered what other people might think about me working outside but I came to realise that actually most people don't care what you do - they're really not interested or perhaps they just don’t feel that they can approach you. Those people that did talk to me were very nice and didn't care whether my picture was good or bad, they were just fascinated at seeing someone having a go at making art in public and so that gave me quite a lot of confidence to do this again in the future

By the end of the month I was a lot less worried about grabbing my gear and just going outside. It’s really all about the experience rather than producing some kind of masterpiece.

I also got a lot less precious about posting to Instagram. I’ve been on a few courses this year about how best to use it and I’ve found that you can tie yourself up in knots about whether to do a reel or a post or a story. Posting every day meant I didn’t have time to worry and it just became part of my daily practice. Plus I picked up a few new followers

So, to answer my question: yes, I would so this sort of challenge again. It’s been a great way of getting past a creative block and trying a new medium and as a result I now have several ideas that I want to explore over the coming months