Shoppers and locals are turning out for Chepstow Pride from Friday 26 to Sunday 28 June, with town-centre parades, theatre, cabaret and a riverside picnic , supported by Chepstow Town Council and Monmouthshire Building Society , and plenty of ways to join the fun whether you’re coming for the parade or a night of queer performance.

Essential Takeaways

  • When and where: Pride runs across Chepstow from Friday 26 to Sunday 28 June, finishing with an 11am parade down High Street on Sunday.
  • Headliners: Tom Marshman’s play Billy Twirling Through Time opens Friday night at the Drill Hall, introduced by Tony Award-winning designer Ian MacNeil.
  • Saturday nightlife: Pride Party Cabaret at the Drill Hall features Bristol duo DTYM and international queer performers , lively DJs and theatrical acts.
  • Community art: A labour movement-style banner, made by local LGBTQIA+ young people, will be displayed in Monmouthshire Building Society ahead of the parade.
  • Family-friendly finish: The festival closes with a community picnic and bandstand performances by the riverside after the parade.

What to expect on parade day , high street, river and picnic vibes

Sunday’s 11am parade down Chepstow High Street is the centrepiece, with a relaxed, community feel and colourful floats, banners and local groups joining in. There’s a real sense of place when you reach the riverside , the bandstand performances and picnic spot make for a good chill-down after the march. If you want a good viewing spot, arrive early and take a blanket; the riverbank fills up quickly.

Theatre night: why Billy Twirling Through Time is a neat opener

The Drill Hall hosts Tom Marshman’s Billy Twirling Through Time on Friday at 9pm, and it’s been given a boost by an introduction from Ian MacNeil, whose design credits include Billy Elliot. That mix of local talent and stagecraft pedigree gives the production extra sparkle , expect a compact, witty evening that’s more theatrical treat than blockbuster. Buy tickets in advance if you’re planning to combine theatre with Saturday’s late-night cabaret.

Saturday cabaret: where to go for queer performance and DJs

Saturday’s Pride Party Cabaret promises “seriously good queer performers and DJs”, with Bristol pair DTYM and international names on the bill. It’s the slot for those who want costume, glitter and a proper night out without leaving town. If you’re sensitive to loud music, check performance times and consider ear protection; otherwise, bring friends and a curious spirit.

The community banner , young people making their mark

A highlight to watch for is the labour-style banner designed and made by young LGBTQIA+ people from Chepstow during workshops at Wyedean School. It’s being publicly displayed at Monmouthshire Building Society during the week beforehand, so pop in and see the artwork up close. The banner feels like more than décor , it’s a visible sign this Pride is rooted in local voices and learning programmes.

Practical tips: planning, parking and accessible options

Chepstow Town Council has the event details and schedules online, and venues like the Drill Hall post tickets and times on their sites. With road closures likely around the High Street on Sunday, plan travel in advance and use public transport where possible. If you need accessible viewing areas or quiet spaces, contact event organisers ahead of time; many community events now offer quieter zones and accessible facilities.

It's a small change that can make every Pride moment feel part celebration, part neighbourly welcome.

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