Discover what’s on in Windsor in October – from Halloween fun at Legoland to live music, food festivals & autumn events you won’t want to miss!
October in Windsor is all about crisp autumn days, golden leaves, and Halloween fun – and we absolutely love it. The summer heat has mellowed, but the weather is still pleasant enough to enjoy a walk through Windsor Great Park or a cosy riverside lunch in town. And if you’re visiting this month, you’ll find there’s a packed calendar of events to enjoy.
For family fun, Brick or Treat at Legoland is running across weekends throughout October and right up to 1 November. It’s full of spooky (but not scary!) Halloween-themed activities – perfect for kids. For the grown-ups, Oktoberfest at Windsor Racecourse is a brilliant night out, with steins of beer, bratwurst, and live music bringing the Bavarian vibes.
There’s also plenty of live entertainment to catch, from the Bollywood panto Surinderella at the Theatre Royal Windsor to the spellbinding Tenebrae Choir performing at the iconic St George’s Chapel. And if you’re a music fan, don’t miss My Girl the River & Serious Child at The Other Space.
October really is a great time to visit Windsor – the town feels festive, there’s loads going on, and the autumn atmosphere is just magic. Scroll down to see what’s happening this month!
2026 Update
October
- 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
- 2-3 October – BetMGM Autumn Friday Raceday @ Ascot Racecourse@ Ascot Racecourse. Tickets: from £19. Website: ascot.com
- 3-30 October – Brick or Treat @ Legoland. Lots of Halloween fun at Legoland. This one is definitely not a frightnight! Website: legoland.co.uk
- 4 October – Ascot Locomotive Society Miniature Railway 2-5pm. Website: ascotlocomotive.co.uk
- 11 October – Susan Calman: Tall Tales @ Theatre Royal Windsor. Tickets: from £32.25. Website: theatreroyalwindsor.co.uk
- 12–17 October – The Mousetrap @ Theatre Royal Windsor. Tickets: from £23.50. Website: theatreroyalwindsor.co.uk
- 17 October – QIPCO British Champions Day @ Ascot Racecourse. Tickets: from £32. Website: ascot.com
- 31 October – Windsor Royal Pumpkin Party. This is a pumpkin carving session and fancy dress party that the kids will absolutely love. Tickets: this is a free event! Website: wrsevents.co.uk
- 31 October – Fireworks Spectacular Family Raceday. @ Ascot Racecourse Tickets: from £29. Website: ascot.com
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.
