01 May 2026
Five Things to See and Do in the Cotswolds This May
Tags: Cotswolds, Staycation, travel, food and drink
StayCotswold has put together five of the highlights worth planning a stay around this month.
• Live music in beautiful surroundings. Two outstanding music festivals take place in May. The Cheltenham Jazz Festival draws world-class performers to one of the region's most elegant Regency towns, while the Chipping Campden Music Festival offers an intimate programme of classical and chamber music in one of the most perfectly preserved market towns in England. Both are well worth planning a stay around.
• Eccentric traditions that cannot be found anywhere else. The Cotswolds has a gift for the gloriously unconventional. The Cooper's Hill Cheese Rolling is exactly what it sounds like and utterly compelling to watch, while the Tetbury Woolsack Races see competitors hauling heavy fleeces up one of the steepest streets in the country. Both are free to attend, both are unforgettable.
• World-class equestrian sport. Equestrian enthusiasts are particularly well served in May, with both the Badminton Horse Trials and the Cirencester Park Horse Trials drawing competitors and spectators from across the country. Whether you are a seasoned follower of the sport or simply after a spectacular day out in exceptional surroundings, both events deliver.
• Circus, cinema and a palace worth exploring. Gifford Circus pitches its big top at Blenheim Palace in May, combining extraordinary live performance with one of the most visited historic houses in Britain. The palace grounds are magnificent in their own right and have served as a backdrop for countless film and television productions. A visit makes for a genuinely special family day.
• Food, drink and walking in equal measure. The Stroud Food and Drink Festival celebrates the region's outstanding independent producers, while the Winchcombe Walking Festival opens up some of the finest waymarked routes in the Cotswolds with guided walks for all abilities. Between them, they offer two of the most enjoyable ways to spend a May afternoon in the area.
StayCotswold offers a hand-selected collection of holiday cottages and properties across the region, from characterful village retreats to contemporary rural escapes. For availability and bookings visit https://www.staycotswold.com
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