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Exploring the Best Festivals in Cheltenham and the Cotswolds: Month by Month

Welcome to Pigeon House Cottage, your charming Bed & Breakfast nestled in the heart of Cheltenham. As the seasons change and the Cotswold countryside comes alive, there's no better time to indulge in the vibrant festival scene that graces our beautiful region. In this article, we'll take you on a delightful journey through some of the most captivating festivals in Cheltenham and the Cotswolds, ensuring that your stay with us is filled with unforgettable memories.




Cheltenham Races: New Year’s Day: A hugely popular event held every New Year’s Day; an excellent way to see in the New Year.


Cheltenham Races: Trials Day: An exciting day of horse racing as the anticipation builds for the renowned Cheltenham Races in March.





Snowdrops at Rococo Gardens: One of the best times of the year to visit the Rococo Garden is when the snowdrops are in full bloom usually in February each year. With one of the largest naturalistic plantings of snowdrops, it is a truly lovely sight.





Cheltenham Races: Gold Cup: A major highlight in the racing calendar, culminating in the world famous Gold Cup.




Cheltenham Races: The April Meeting: Immerse yourself in the thrill of horse racing at The April Meeting, a highlight on Cheltenham's social calendar.


Cheltenham Wine Festival: Explore and taste over 300 different wines and meet the people behind them.




Great Western Steam Railway: Cotswold Festival of Steam Offers steam train fans and families a full agenda of entertainment and train rides.


RHS Show: Explore the beauty of flora and horticulture at the RHS Show, a stunning display of nature's finest creations


Badminton Horse Trials: An annual International three day event, culminating in the cross-country day which attracts crowds of up to a quarter of a million people.


Cheltenham Jazz Festival: Boasting Jamie Cullum and Moira Stuart as some of their biggest fans, the Cheltenham Jazz Festival brings a mix of international jazz icons, up-and-coming news artists and unique festival exclusives.


Cooper’s Hill Cheese Rolling: A centuries old tradition with spectators coming from far and wide to see competitors race down a near vertical hill after a wheel of double Gloucester cheese.


Tetbury Wool Sack Races: 240 yards up a 1 in 4 hill, carrying a 60lb (35lb for women) sack on your back. Originally thought to have started in the 17th Century and officially Been going for more than 30 years.




Wychwood Festival, Cheltenham Racecourse: Dance to live music and celebrate the arts amidst the scenic backdrop of Cheltenham Racecourse.

Cheltenham Three Peak Challenge, Crickley Hill: Embark on an adventurous journey through Crickley Hill, conquering its three peaks and enjoying breathtaking views.


Malvern 3 Counties Show: Delight in the diverse showcase of rural life, crafts, and entertainment at the Malvern 3 Counties Show


Prescott Bike Festival Prescott Hill Climb: Experience the exhilaration of motorcycle displays and races at Prescott Hill Climb's vibrant Bike Festival


Cheltenham Science Festival: Attracting some of the world’s greatest scientists and comedians, Cheltenham Science Festival hosts some fascinating talks challenging and debating some of the great unknowns. A free interactive exhibition is held in the Town Hall for the duration of the event.


Cheltenham Food & Drink Festival: A three day event in the heart of Cheltenham, showcasing a vast range of food and drinks, as well as hosting events such as wine tastings, food talks and cookery demonstrations.





Cheltenham Paint Festival: Witness the transformation of Cheltenham's walls into colourful canvases during the dynamic Cheltenham Paint Festival.


The Game Fair: Immerse yourself in the world of outdoor pursuits and country living at The Game Fair, a celebration of rural heritage.


2000 Trees Festival, Upcote Farm: Indulge in live music from various genres in the serene setting of Upcote Farm during the 2000 Trees Festival.


Postlip Beer Festival: Savour a variety of artisanal beers while enjoying the picturesque surroundings of the Postlip Beer Festival.


Cotswold Lavendar Farm: Immerse yourself in the fragrant beauty of the Cotswold Lavender Farm, a sensory delight for nature enthusiasts.


Cheltenham Cricket Festival, Cheltenham College: Experience the grace and excitement of cricket matches at the historic Cheltenham College grounds.


Cheltenham 7’s Festival, Newlands Park: Join the exhilarating rugby festivities at Newlands Park during the Cheltenham 7’s Festival.


Summer Jam, Brewery Quarter: Indulge in live music, delicious food, and a lively atmosphere at the Brewery Quarter's Summer Jam event.


Cheltenham Music Festival: One of the most prestigious music festivals in the world, the Cheltenham Music festival offers a fantastic programme of concerts across several Cheltenham venues, including the Town Hall, the Pittville Pump Rooms. Over 60 events with 650 performers across the 12 day festival.


Royal International Air Tattoo: The World’s largest military air show full of dramatic displays and spectacles!


Stroud Country Show: Dating back to Victorian times, the Stroud Show has lots of crafts and produce from around the region, with music, beer tents and local food, making a great day out.


Cotswold Show: Based in Cirencester park, the two day Cotswold Show and Food Festival is a great day out, with everything from falconry displays to cookery demonstrations, dog agility courses and brass bands!


Air Balloon Festival, Cheltenham Racecourse: Watch the sky come alive with vibrant hot air balloons at the Air Balloon Festival, a mesmerizing sight to behold.


DubFest: Immerse yourself in the world of Volkswagen culture and music at the lively DubFest event.


Great Western Steam Railway Beer & Ale Festival: Delight in a wide selection of beers and ales while surrounded by the nostalgia of Winchcombe Station.





Festival of British Eventing: Set in Gatcombe park, the Festival of British Eventing encompasses the British Open, Intermediate and Novice Championships as well as the Amateur Championship, The Corinthian Cup.


Big Festival: Situated on Alex James’ farm in the North Cotswolds, this three day foodie extravaganza also features a cracking musical line up.


Stroud Fringe: A free music and arts festival in Stroud celebrating the towns musical and artistic talents, with live bands, street food and entertainment.


Frocester Beer Festival: Annual festival with over 100 different cask-conditioned real ales from breweries throughout the UK. Live-music, hot food and a large selection of wines are also included.




Moreton-in-Marsh Country Show: Experience the charm of the countryside at the Moreton-in-Marsh Country Show, featuring traditional activities and entertainment.


Heritage Open Days: Discover Cheltenham's rich history as local heritage sites open their doors to the public during the Heritage Open Days.


Three Counties Malvern Autumn Show: Celebrate the autumn season with a showcase of harvest produce, gardening, and artisanal goods.


RHS Autumn Show: Immerse yourself in the vibrant colours and textures of autumn at the RHS Autumn Show, a feast for the senses.


Five Valleys Walk: In aid of Meningitis Now, this sponsored walk covers the Five Valleys. Attracting thousands of visitors of all ages, and four-legged friends, the full walk is 21 miles. Participants can, however pick a shorter distance if they wish.


Blenheim Horse Trials: An annual three day event attracting some of the world’s best event horses and riders.




Cheltenham Races: The Showcase: Witness the excitement of The Showcase, a prestigious event that kicks off the jump racing season at Cheltenham Racecourse.


Autumn Colours at Westonbirt Arboretum: The best time of year to visit the arboretum; the autumn colouring of the leaves is quite spectacular.


Cheltenham Literature Festival: A literary lover’s dream, the Cheltenham Literature festival is packed full of writers, actors, politicians making up the 10 day programme with debates, interviews, talks and workshops for everyone.





Cheltenham Races: Paddy Power: Join the exhilaration of horse racing and entertainment at the Paddy Power event at Cheltenham Racecourse.




Cheltenham Races: International Meeting: Experience the thrill of international horse racing and the festive atmosphere at the Cheltenham Races' International Meeting.


Festival of Lights, Sudeley Castle: Be enchanted by the magical Festival of Lights at Sudeley Castle, a captivating display of illuminated wonder.

Bibury Duck Race: Every boxing day, hundreds of spectators gather for this annual charity duck race, with thousands of yellow ducks floating along the river Coln through the village.


We look forward to hosting you at Pigeon House Cottage and being part of your memorable experiences during these exciting events in Cheltenham!

At Pigeon House Cottage, we're not only dedicated to providing you with a haven during your stay but also to ensure you create cherished memories by exploring the vibrant festivals of Cheltenham and the Cotswolds. From the soulful tunes of jazz to the literacy wonders of Cheltenham Literature Festival and the delectable delights of the Cotswold Food and Drink Festival. Our region is a treasure trove of experiences waiting to be discovered. So, pack your bags, embrace the festive spirit, and make the most of your stay with us in this enchanting corner of the world.


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