Events in Gloucester From 25th May – 31st May 2026

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You can find events in Gloucester this week that cover the city’s history and live music. This week includes guided walks through Gloucester’s past, starting from its founding as Glevum in AD 48 and continuing through the medieval era. The city’s development around Gloucester Cathedral and its role during the First English Civil War in 1643 are part of the story. On the River Severn or in the Gloucester and Sharpness Canal, you can walk along routes that shaped the city’s growth. The Fosse Way, the railway, and the M5 motorway remain key to how people access the area. You’ll also find evening music sets and social events in the city centre. For the best experience, plan ahead, Southgate Street and the historic docks can be busy, and parking near the riverside is limited. Travel by bus or train to avoid congestion. Check the listings below for times and locations. If you’re visiting, note that some venues are outside the city centre, just outside the city or a short drive away.

Monday 25th May

City Guided Walk With Gloucester Civic Trust

· Gloucester BID · Culture & Arts

A 90-minute guided walk exploring Gloucester's history from Roman to Victorian times.

Tuesday 26th May

Walk Yourself Fit With Bev

· Deans Walk Inn · Fitness & Outdoors

A inclusive walking event led by Bev, welcoming participants of all abilities.

Thursday 28th May

Wychwood Festival

· Nightlife & Music

Wychwood Festival takes place at Cheltenham Racecourse featuring music and performances.

Saturday 30th May

Expanse - 30th May @ Cafe Rene - Ibiza Classics - Free Entry

· Nightlife & Music

DJ set at Cafe Rene featuring Ibiza Classics with free entry.

Sunday 31st May

Unified Dating - Meet Singles in Gloucester

· Nightlife & Music

A social event hosted by Unified Dating to help singles meet new people in Gloucester.