With the return of Gloucestershire's famous Cheese Rolling and shin-kicking at the Cotswold Olimpick Games, May is the month to see some of the county's wackiest traditions in action!
Plus, with pride events, secret foodie openings and big-name musicians performing at this year's Cheltenham Jazz Festival, don't miss SoGlos's pick of 10 best things to do this month.
Catch a gig under the Big Top at Cheltenham Jazz Festival
Kicking off Cheltenham Festivals' 80th anniversary year with six days of electrifying live music, Cheltenham Jazz Festival brings the world's finest jazz musicians, pop icons and big bands to Gloucestershire from Wednesday 30 April to Monday 5 May 2025.
With over 60 artists on the lineup, from soul legend Beverley Knight to The Who frontman Roger Daltrey, jazz fans can also see up-and-coming local musicians perform at pop-up shows in Cheltenham's pubs, bars and entertainment venues as part of the free '... around town' programme.
See Here's who's coming to Cheltenham Jazz Festival in 2025 for SoGlos's handpicked highlights.
Chase the cheese at Gloucestershire Cheese Rolling
One of Gloucestershire’s craziest traditions, the annual Cheese Rolling competition is returning to Cooper’s Hill on Monday 26 May 2025, giving daring competitors the chance to peg it downhill after that coveted wheel of Double Gloucester.
Attracting hundreds of spectators and brave participants, who rarely manage to stay on their feet in pursuit of the cheese, this world-famous event is not to be missed.
Go bluebell spotting in Gloucestershire
With seas of blue flowers transforming Gloucestershire’s landscape, May is the best time to see bluebells in the county, with remarkable displays at popular attractions like Westonbirt Arboretum, as well Cam Peak and other local beauty spots.
Providing some picture-perfect inspiration for floral fans, check out SoGlos’s 11 favourite places to see bluebells in Gloucestershire to soak up the spectacle this month.
Explore Slimbridge's new Estuary Shoreline landscape
There's a brand new area for visitors to explore at Slimbridge Wetland Centre's sprawling nature reserve, with Estuary Shoreline opening on Friday 9 May 2025.
Offering a place to relax, play or tuck into an alfresco lunch, Estuary Shoreline is an immersive and accessible outdoor area with playful features like giant lily pad stepping stones, a shoreline beach to unwind by the water and new opportunities to connect with wetland wildlife.
Chow down on dirty burgers at The Woozy Pig's new restaurant
Cult burger, banger and barbecue brand, The Woozy Pig, is opening its first standalone restaurant in Cheltenham this month, with the launch date set for Friday 9 May 2025.
Located between Baker & Graze and Bhoomi Kitchen in The Suffolks, the finer details about the new space have been kept under wraps so far, but diners can expect all the Woozy classics, with a menu spanning brunch, lunch, dinner, cocktails and beer.
Cheer on the shin-kickers at the Cotswold Olimpick Games
Witness one of the UK's most fascinatingly weird sporting trials up on Dover's Hill, when the Cotswold Olimpick Games returns on Friday 30 May 2025.
Promising plenty of hammer throwing, shot putting and shin-kicking action, watch all the wacky contests unfold before the sky is illuminated with fireworks and the torch-lit procession leads the way back to Chipping Campden for the after party!
March in Cheltenham's pride parade
Show your pride for Cheltenham's LGBTQIA+ community in this year's pride parade, meeting outside John Lewis and travelling through town in a powerful statement of visibility on Saturday 17 May 2025.
The parade finishes at Imperial Gardens, just in time for Pride in Cheltenham to kick off — with headline performances from RuPaul's Drag Race UK star Kitty Scott-Claus and twin duo Billy & Louie, who you might recognise from The Voice. Don't miss the ever-paw-pular dog show and the after party at Popworld, too.
Watch the dragon boats race at Gloucester Docks
Bringing with it a boat load of entertainment, Gloucester’s annual Dragon Boat Festival is racing back into town on Sunday 18 May 2025.
See dozens of colourful dragon boats go head-to-head, with around 30 teams vying for victory — and the prized Gloucester Dragon Boat Shield! — at this vibrant annual event down at Gloucester Docks. And there's funfair entertainment for children, too.
Uncover the secret location of Cheltenham's newest fine dining experience
Restaurant Journey is returning to Cheltenham with a new, immersive dining exeperience in a secret location, which diners can only find by following a series of hints and clues...
Set in a 16-cover 'secret space', the 10-course dining concept combines bold flavours, creative cooking techniques and theatrical storytelling to create a foodie experience that's 'unlike anything Cheltenham has seen before' — running just three evenings a week from Friday 2 May until Thursday 31 July 2025.
Wander around Barnsley's beautiful gardens at the famous village festival
Turning 35 this year, Barnsley Village Festival brings classic cars, Morris dancing, live music and more to the Cotswolds on Saturday 17 May 2025.
Founded by late British gardening icon, Rosemary Verey, the ever-popular annual festival presents the chance to tour around some of Gloucestershire's most gorgeous gardens — including the grounds of THE PIG Hotel, which are usually open to hotel guests only.
