Find the places to enjoy live music and comedy shows across Winchester district
Looking to be entertained? Enjoy belly-laughs and foot-tapping rhythms with our round-up of music and comedy – from regular Jazz nights, to touring comedy shows and annual festivals, there are options to suite any taste.
Curated by the Visit Winchester team.
Created: 17 August 2026.
Theatre Royal Winchester
From tours, to panto, to work in progress, to regular Winchester Comedy Festival Galas, Theatre Royal Winchester regularly hosts a huge selection of comedy shows and performances. They also host a variety of music nights from tribute acts to themed shows and musical theatre performances. Head to their website and ‘filter’ through What’s On to discover something new.
📍Winchester city centre
The Railway Inn
The Railway Inn is Winchester’s dedicated music venue, hosting music almost every night of the week spanning genres and generations. They support open mic nights, poetry jams and comedy nights too!
📍Winchester city centre
The Northbrook Arms
Hosted by local comedian Paul McCaffrey (of Impractical Jokers fame) the Northbrook Arms put on an evening of stand up comedy most months.
📍East Stratton
St James Tavern
Get your dancing shoes on or just sit back and relax and enjoy monthly contemporary jazz evenings with Cinnamon Jazz, or acoustic blues with Jon Walsh.
📍Winchester city centre
The Nutshell
The Nutshell host monthly comedy club and jazz club nights. They also offer scratch nights for emerging performers to test new work; and Jazzbops – a lunchtime jazz concert made especially for grown-ups and their little ones aged 0-4. Check out the rest of their programming too, there is loads of comedy and music in the mix!
📍Winchester city centre
Bishops Waltham Festival
Alongside the main festival each June, the Bishops Waltham Festival committee organise a series of events across the year, this usually includes at least one comedy night and one concert.
📍Bishop’s Waltham
The Arc
The Arc offer monthly ‘acoustic café’ sessions, bringing amazing artists to the café bar in a relaxed evening of music. In the main performance space The Arc programme a variety of music and comedy acts from across the UK and beyond.
📍Winchester city centre
Winchester Royal Hotel
Winchester Royal Hotel offer a selection of themed music evenings making use of their beautiful walled garden in the summer and their spacious lounge in the winter months.
📍Winchester city centre
The Crown Inn
Most weekend The Crown Inn present live music with regular performers and guests alongside themed evenings and party nights.
📍Bishop’s Waltham
The Square Cow
This traditional village pub has regular music performances spanning all genres with a variety of afternoon and evening sessions to enjoy with a cold drink.
📍Wickham
The Hospital of St Cross
The Brothers of St Cross curate a series of Thursday Lunchtime Concerts, providing local music students the opportunity to perform in the beautiful surroundings of Chapel of St Cross. There is also regular touring concerts hosted throughout the year.
📍Winchester city
Stitches Comedy Club
Fantastic professional comedians perform at these regular comedy nights, and even some faces you'll recognise off the telly! This touring event often visits Alresford Recreation Centre and Wickham Community Centre which both offer an intimate setting and fully stocked bar.
📍Wickham 📍Alresford
Winchester Cathedral
Alongside regular evensong and traditional bell ringing, Winchester Cathedral also host lunchtime concerts with students from around the country most Tuesdays. They also offer Jazz Lates in the Café Garden and bespoke and themed shows and performances in the main cathedral space throughout the year.
📍Winchester city centre
The King’s Head
Wickham's much-loved village pub host monthly comedy nights and regular music. Pop, Country, Opera, Rock and even Eurovision!
📍Wickham
Worthies Sports and Social Club
The Worthies music offering includes regular themed nights in Rock, Soul and Motown. They also host a monthly Jazz Jam, welcoming local musicians for a free jam session.
📍Kingsworthy
Helch Market
Helch Market plays host to a variety of regular entertainment. Jazz Club welcomes live Jazz artists, ‘Genres’ sees a DJ spin a selection of classic floor fillers, Super Break sessions celebrate all things Soul, Funk, Hip Hop and Funky Fridays are guaranteed to keep you on the dance floor. Alongside this there is Helch Comedy Club - a different line up of top of the class comedians every Sunday evening!
📍Winchester city centre
The March Hare
The March Hare regularly host music nights have a large garden perfect for summer evenings. In 2026 they are hosting their own music festival!
📍Harestock
Winchester Guildhall
One of Winchester’s largest venues, the Guildhall hosts regular concerts and is your opportunity to take in shows celebrating movie and musical greats with orchestras and bands taking centre stage.
📍Winchester city centre
Don’t forget to check out our Festivals in Winchester page to check out the latest music and comedy offerings from our festivals. From Jazz and Comedy to Drum and Bass and Folk music – there’s something for everyone.
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