Are you wondering what to do in Windsor in May? Explore the latest events, family days out and the best places to enjoy spring in town.
I am incredible biased, but May is the best month of the year, isn’t it? It’s got not one, but two bank holidays, and the weather actually starts getting properly hot. It really feels like we’re stepping into summer. The days are longer, the parks are looking lush, and there’s that lovely sense that everyone wants to be outside making the most of it. May also marks the start of tourist season in Windsor – things really do start getting a lot busier in town.
When it comes to events and activities, there is plenty going on in May. With the early May bank holiday and half term at the end of the month, there’s loads happening across town. Windsor Racecourse has some brilliant family-friendly fixtures this month, including the Big Bank Holiday Family Fun Day on 4 May and Football Mania Family Fun Day on 25 May, which should be amazing with kids. Over at LEGOLAND, the LEGO Festival kicks off in May, making it such a fun time for families planning a big day out.
For things to do indoors, May still brings a great mix of live music, comedy and theatre, and it’s always worth checking what’s on at Theatre Royal Windsor for those rainy spring evenings. But honestly, this is the month where Windsor really shines outdoors – think boat trips on the Thames, al fresco lunches, castle walks and long golden evenings by the river.
I’d definitely recommend saving this page and checking back throughout the month too. I’ll keep it as up to date as possible, so whenever you’re looking for inspiration for what’s on in Windsor in May, you’ll have plenty of ideas right here.
May 2026
- 1 May – Bump to Tots Breakfast Club @ The Other Space (10:00-12:00) – relaxed meet‑up for parents
- 1 May – Royal Ascot Trials Day @ Ascot Racecourse. Tickets: from £19. Website: ascot.com
- 2 May – Symphonic Abba @ Windsor Parish Church. Tickets: from £25. Website: eventbrite.co.uk
- 3 May – Sunday Reset @ The Other Space (10:30-11:30)
- 4 May – May Day Family Fun Day @ Windsor Racecourse. Tickets: from £21 (children 17 and under go free). Website: windsor-racecourse.co.uk
- 4 May – Eton May Day Fete @ Eton Recreation Ground (12pm – 4pm) – this is set to be a fun afternoon for the whole family, and it’s free!
- 6–16 May – You Will Find Me @ Theatre Royal Windsor. Tickets: from £19.50. Website: theatreroyalwindsor.co.uk
- 8 May – Bump to Tots Breakfast Club @ The Other Space (10:00–12:00) – relaxed meet‑up for parents
- 8-9 May – Peroni Nastro Azzurro 0.0% May Friday Raceday @ Ascot Racecourse. Tickets: from £19. Website: ascot.com
- 9 May – UZ MI LIVE @ The Other Space (20:00-23:00)
- 10 May – Sunday Reset @ The Other Space (10:30-11:30)
- 11 May – Residents Racenight 2026 @ Windsor Racecourse. Tickets: from £24. Website: windsor-racecourse.co.uk
- 11 May – A Cumberland Conversation with Dr Rowan Williams @ Cumberland Lodge. Tickets: from £25. Website: cumberlandlodge.ac.uk
- 14–17 May – Royal Windsor Horse Show. Tickets: from £31. Website: rwhs.co.uk
- 15 May – Bump to Tots Breakfast Club @ The Other Space (10:00-12:00) – relaxed meet‑up for parents
- 16 May – Windsor Vegan Fiesta @ Peascod Street (10:30-17:00)
- 17 May – Sunday Reset @ The Other Space (10:30-11:30)
- 17 May – Ben Portsmouth – This Is Elvis @ Theatre Royal Windsor. Tickets: from £29.25. Website: theatreroyalwindsor.co.uk
- 17 May – Ascot Farmers Market – fresh produce & artisan goods. Free entry
- 17 May – Windsor Jazz Club: Michael Wilkins Quartet @ Alma Road. Tickets: from £10
- 18 May – Flavours of India – Monday Night Racing @ Windsor Racecourse. Tickets: from £24. Website: windsor-racecourse.co.uk
- 19–23 May – Frankie Goes to Bollywood @ Theatre Royal Windsor. Tickets: from £29.50. Website: theatreroyalwindsor.co.uk
- 21 May – Small99’s People, Planet, Pint: Sustainability Meetup @ The Other Space (19:00–22:00)
- 22 May – Bump to Tots Breakfast Club @ The Other Space (10:00–12:00) – relaxed meet‑up for parents
- 23 May – Summer Opening Party 2026 ft. Decade Explosion – Summer Saturday racing @ Windsor Racecourse. Tickets: from £24. Website: windsor-racecourse.co.uk
- 24 May – Sunday Reset @ The Other Space (10:30-11:30)
- 24 May – Open Deck (Bring Your Own Vinyl) @ The Other Space (13:00-18:00)
- 25 May – Spring Bank Holiday Family Fun Day @ Windsor Racecourse. Tickets: from £24. Website: windsor-racecourse.co.uk
- 27 May – 6 June – The Marquise @ Theatre Royal Windsor. Tickets: from £23.50. Website: theatreroyalwindsor.co.uk
- 29 May – Bump to Tots Breakfast Club @ The Other Space (10:00–12:00) – relaxed meet‑up for parents
- 29 May – The Butterfly House @ Victory Field Recreation Ground, Ascot (11:15–12:20, 12:30–13:30 and 13:45–14:45). This is a show inspired by nature and is aimed at 2-10 year olds
- 31 May – Sunday Reset @ The Other Space (10:30-11:30)
