Entertainment in Winchester

The Theatre Royal Winchester is your number one option for seeing a show in Winchester. It’s been the entertainment venue of choice in this town for more than 100 years. With its plush 400-seat Edwardian-style auditorium and extravagant programme of drama, music, dance, comedy, and pantos, it attracts more than 70,000 visitors a year, with as many as 200 performances. The Theatre welcomes top-class touring productions from across the UK, including musicals from the West End, thanks to its surprisingly large stage. If you want a bite before your visit, some of our favourite places to eat in Winchester are right on the Theatre Royal’s doorstep.

We’d highly recommend checking what’s on at the Winchester Discovery Centre during your stay at our Winchester hotel. It’s the main local library on Jewry Street, but it also houses a great art gallery, exhibition space, studio theatre and performance hall. Every month, the Winchester Discovery Centre books as many as 150 events, gigs, concerts, talks, and shows. It means more than half a million visitors pass through its doors each year. Even if there are no events on, it’s worth exploring the gallery, which enjoys a good relationship with the Tate and regularly puts on some excellent exhibits.

It’s also worth mentioning the Chesil Theatre on Chesil Street. It’s home to the Winchester Dramatic Society, which takes to the stage of this 75-seat former church with six productions per year. It’s only small, but there’s some serious talent in this local Am Dram society.

Winchester City FC is the town’s one and only football club. They play at The City Ground, just a fifteen-minute walk from the town centre. The club dates back to 1884, but in its long history The Citizens have never played in the Football League. Home fixtures are on Saturdays at 3pm. Adult tickets are less than a tenner, and children under 12 go free, so it’s an inexpensive way to enjoy some sport on a Saturday.

Next door in North Walls Park is where you can also find Winchester Rugby Club. It’s one of Hampshire’s largest and most successful amateur rugby clubs with teams across all age groups, with first XV fixtures on Saturdays.

Before we get to Winchester’s live music venues, we need to tell you about Boomtown Fair, the annual four-day festival that takes over the Matterley Estate near Winchester every August. Every year marks the beginning of a new chapter for the festival, and with it an ever-evolving storyline that’s reflected in the design of the festival site’s several districts, streets, stages, and venues. Visually, Boomtown is completely unique, as far as UK festivals go. It takes the general good-natured vibe of Glastonbury, and presents it with all the showmanship of Belgium’s Tomorrowland. The artists booked for Boomtown gets better with every chapter, as shown by recent headliners Gorillaz putting on a show to remember.

In terms of local live music options, we’ve waxed lyrical about some of our favourite pubs for live music among our Winchester nightlife recommendations. A couple of other honourable mentions go to O’Neill’s, the popular chain of Irish pubs on the High Street where you can enjoy live music every Friday, Saturday and Sunday. There’s also The Railway. As the name suggests, you’ll find it next to Winchester Station. As a public house it dates back to the 1850s. It’s the longest-running live music venue in Winchester, with gigs on most days of the week.