Wondering what’s on in Windsor in September? From food festivals to autumn races & other events, here’s everything happening this month!
September is such an underrated time to visit Windsor. The summer crowds start to fade, the pace slows down a little, and the weather is often still beautifully warm and sunny – perfect for exploring the town without the hustle and bustle. Whether you’re looking for culture, live music, foodie experiences or a new fitness challenge, September has it all.
One of the biggest highlights this month is the Windsor Festival, running from 13–30 September. With events across some of Windsor’s most iconic venues – including Windsor Castle – it’s a brilliant way to experience the town’s cultural side. History lovers will also enjoy the Royalists and Rebels weekend at the Castle, bringing the past vividly to life.
There’s plenty happening at Windsor Racecourse, too, including the Final Monday Night Racing on 1 September and the foodie-filled Big Ascot Food & Wine Weekend. If you’re more into running shoes than racecards, the Windsor Women’s 10k and Windsor Half Marathon are great ways to get involved locally.
Chloe and I love September in Windsor – it’s quieter, cooler and still packed with things to do. Keep scrolling to see what’s on and get planning your perfect early autumn day out!
2026 Update
September
- 3 September – Royal Free Singers (Open Evening). Website: royalfreesingers.org.uk
- 3–12 September – Chariots Of Fire @ Theatre Royal Windsor. Tickets: from £23.50. Website: theatreroyalwindsor.co.uk
- 4-5 September – The Big Ascot Food & Wine Race Weekend @ Ascot Racecourse. Tickets: from £19. Website: ascot.com
- 5 September – Windsor Morris Dancers Performance. Website: windsormorris.org.uk
- 6 September – Ascot Locomotive Society Miniature Railway 2-5pm. Website: ascotlocomotive.co.uk
- 7 September – Monday Afternoon Flat Racing @ Windsor Racecourse. Tickets: from £24. Website: windsor-racecourse.co.uk
- 12 September – 3 October – Windsor Festival. This is a big festival at event spaces all over Windsor. Tickets: some events are free, some are ticketed. Website: windsorfestival.com
- 13 September – Ascot Farmers Market – fresh produce & artisan goods. Free entry
- 14 September – Flat Season Finale @ Windsor Racecourse. Tickets: from £24. Website: windsor-racecourse.co.uk
- 19 September–11 October – The Windsor Fringe. This is the second oldest fringe festival in the UK. Tickets: some events free. Website: windsorfringe.co.uk
- 22 September – Jazz Sabbath Tour @ The Old Court, Windsor.
- 26 September – Windsor Womens 10km. A fun 10km race around Windsor specifically aimed at women. Tickets: from £30.50. Website: windsorwomens10k.com
- 27 September – Windsor Half Marathon. This is one of the best running events around Windsor. Tickets: from £42. Website: runwindsor.com
- 30 September – 3 October – The Anastasia File @ Theatre Royal Windsor. Tickets: from £23.50. Website: theatreroyalwindsor.co.uk
Don’t forget you can plan the rest of your year with our big events calendar! This should give you a really good overview to the year, so make sure you bookmark it and keep on coming back.
