What to do in Windsor and Maidenhead in October 2026

A guide to events, concerts, and experiences in Windsor and Maidenhead during October 2026.

37 results

Local time in Windsor and Maidenhead (Europe/London), not your device time.Local time (Europe/London)

Mon, Oct 12 – Fri, Oct 16

Mon, Oct 12 · 10:00 AM GMT+1

Legoland Windsor - Daily Entry

Mon, Oct 12 · 10:00 AM GMT+1

Legoland Windsor · Windsor

Tue, Oct 13 · 10:00 AM GMT+1

Legoland Windsor - Daily Entry

Tue, Oct 13 · 10:00 AM GMT+1

Legoland Windsor · Windsor

Wed, Oct 14 · 10:00 AM GMT+1

Legoland Windsor - Daily Entry

Wed, Oct 14 · 10:00 AM GMT+1

Legoland Windsor · Windsor

Thu, Oct 15 · 10:00 AM GMT+1

Legoland Windsor - Daily Entry

Thu, Oct 15 · 10:00 AM GMT+1

Legoland Windsor · Windsor

Thu, Oct 15 · 12:00 PM GMT+1£32

Windsor Castle

Thu, Oct 15 · 12:00 PM GMT+1

Windsor Castle · London

£32

Fri, Oct 16 · 10:00 AM GMT+1

Legoland Windsor - Daily Entry

Fri, Oct 16 · 10:00 AM GMT+1

Legoland Windsor · Windsor

Fri, Oct 16 · 7:00 PM GMT+1£18.70

October's Comedy in Holyport

Fri, Oct 16 · 7:00 PM GMT+1

Holyport Memorial Hall · Maidenhead

£18.70

Saturday, October 17

10:00 AM GMT+1

Legoland Windsor - Daily Entry

10:00 AM GMT+1

Legoland Windsor · Windsor

10:30 AM GMT+1

Qatar Racing British Champions Day

10:30 AM GMT+1

Ascot Racecourse · Ascot

7:00 PM GMT+1Free

UZ MI LIVE / LABLE PARTY

7:00 PM GMT+1

Other Space Arts

Free

7:00 PM GMT+1£22

October's Comedy at Cordes Hall

7:00 PM GMT+1

Cordes Hall · Sunninghill

£22

Sun, Oct 18 – Fri, Oct 23

Sun, Oct 18 · 10:00 AM GMT+1

Legoland Windsor - Daily Entry

Sun, Oct 18 · 10:00 AM GMT+1

Legoland Windsor · Windsor

Mon, Oct 19 · 10:00 AM GMT+1

Legoland Windsor - Daily Entry

Mon, Oct 19 · 10:00 AM GMT+1

Legoland Windsor · Windsor

Tue, Oct 20 · 10:00 AM GMT+1

Legoland Windsor - Daily Entry

Tue, Oct 20 · 10:00 AM GMT+1

Legoland Windsor · Windsor

Wed, Oct 21 · 10:00 AM GMT+1

Legoland Windsor - Daily Entry

Wed, Oct 21 · 10:00 AM GMT+1

Legoland Windsor · Windsor

Thu, Oct 22 · 10:00 AM GMT+1

Legoland Windsor - Daily Entry

Thu, Oct 22 · 10:00 AM GMT+1

Legoland Windsor · Windsor

Thu, Oct 22 · 6:00 PM GMT+1£7

Plate up & perform

Thu, Oct 22 · 6:00 PM GMT+1

Lancaster

£7

Fri, Oct 23 · 10:00 AM GMT+1

Legoland Windsor - Daily Entry

Fri, Oct 23 · 10:00 AM GMT+1

Legoland Windsor · Windsor

Saturday, October 24

10:00 AM GMT+1

Legoland Windsor - Daily Entry

10:00 AM GMT+1

Legoland Windsor · Windsor

3:00 PM GMT+1£17.50

R&B Lovers - Saturday 24th October - Arch 2 [TICKETS ON SALE NOW!]

3:00 PM GMT+1

Arch 2 · Windsor

£17.50

4:00 PM GMT+1£15

80s & 90s Over 30s Daytime Clubbing - WINDSOR

4:00 PM GMT+1

Labyrinth Nightclub Windsor · Windsor

£15

Sun, Oct 25 – Mon, Oct 26

Sun, Oct 25 · 10:00 AM GMT

Legoland Windsor - Daily Entry

Sun, Oct 25 · 10:00 AM GMT

Legoland Windsor · Windsor

Sun, Oct 25 · 9:00 AM GMT£32

Maidenhead Half Marathon & 10k

Sun, Oct 25 · 9:00 AM GMT

Moorfield Terrace · Maidenhead

£32

Mon, Oct 26 · 10:00 AM GMT

Legoland Windsor - Daily Entry

Mon, Oct 26 · 10:00 AM GMT

Legoland Windsor · Windsor