The Quirky Side of The Cotswolds Festivals with a Twist

Date:
April 24, 2025

The Cotswolds may be known for its postcard-perfect villages, golden stone cottages, and rolling hills, but scratch the surface and you’ll discover a wonderfully eccentric spirit that comes alive in its local English events. From flying cheese to fancy dress races, the Cotswolds knows how to celebrate in style — and sometimes, in the most delightfully bizarre ways.

1. Cheese Rolling at Cooper’s Hill (Brockworth, Gloucester)

Perhaps the most famous of all, this annual event is as mad as it is marvellous. Every spring, crowds gather at Cooper’s Hill to watch (and often wince) as daring competitors hurl themselves down a ridiculously steep slope chasing a round of Double Gloucester cheese.

It’s fast, it’s chaotic, and it’s pure Cotswold madness. Spectators love the carnival atmosphere, and even if you’re not brave enough to join the chase, it’s worth attending just to soak up the thrill.

2. The Cotswold Olimpicks (Dover’s Hill, Chipping Campden)

Dating back to the early 1600s, this eccentric event blends history, sport, and unfiltered fun. Expect events like shin-kicking, tug-of-war, and wheelbarrow races — all held with tongue firmly in cheek. The day ends with fireworks and a torch-lit procession through Chipping Campden, making it one of the most memorable nights on the local calendar.

3. Tetbury Woolsack Races

Ever wanted to race uphill carrying a sack of wool? In Tetbury, you can. Held on Spring Bank Holiday Monday, this event sees competitors — some in costume — hauling 60lb woolsacks up a steep street. It’s a nod to the town’s wool-trading past, and the crowds lining the route make it a fun, festive day out.

4. The Big Feastival (Kingham)

For something slightly less bruising, the Big Feastival, hosted on Alex James’s farm, blends music, food, and family-friendly fun. With top chefs, big-name bands, and activities for all ages, it’s a modern festival with a Cotswold twist — and yes, there’s plenty of cheese involved here too.

5. Giffords Circus (Various Cotswold Locations)

This whimsical travelling circus, beloved by locals, brings magic and mayhem wherever it sets up its big top. With live music, original theatre, acrobatics, and traditional circus arts, it’s a celebration of creativity — set against a charming rural backdrop. Don’t be surprised if you leave grinning from ear to ear.

Why We Love These Events

These quirky Cotswolds events aren’t just for laughs (though they certainly deliver those) — they’re a celebration of community, history, and the wonderfully eccentric character of the Cotswolds. For visitors, they offer a glimpse into the local spirit — one that doesn’t take itself too seriously and welcomes everyone with open arms (and maybe a flying cheese wheel).

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