Win a £2,000 Times Holidays voucher with The Sunday Times Where Was I? competition

Imagine turning a travel clue into your next dream break. The Sunday Times invites readers to follow a playful clue about a historic town and answer two short questions for a chance to win.

The clue notes a town known for a river and a famous castle, and connects to a 15th century battle. You will be asked to name the former county town and the battle mentioned, and then complete an entry form before the closing date.

The prize is a £2,000 voucher to spend on your choice of trip with Times Holidays, giving you the freedom to book a winter sun escape, a luxury cruise, a city break or a walking adventure with a partner network that covers a wide range of destinations.

How to enter is straightforward: answer the two questions and fill out the entry form by the stated deadline, with one entry per person. The closing date for entries is Thursday 29 October 2026.

Times Holidays brings ideas and inspiration for travel to life, helping readers turn imagination into real getaways, with a variety of itineraries and experiences to choose from. The prize can be used for a single complete booking for you and your guests, or as part payment toward a higher-value break, depending on your plans.

Take a moment to imagine stepping into a new city, tasting new foods, and collecting memories on a dream break. If you love travel, puzzle solving and a touch of adventure, this competition could be your ticket to a memorable escape with the flexibility and variety of Times Holidays options.