Cheltenham Festivals & Major Events Guide 2025
Are you a lover of cultural festivals and major sports events? If yes, Cheltenham 2025 promises to give something unique and faithful to the regency and spa heritage. The festival is perfect for refreshing your mind, body, and soul on a year-round packed calendar. The Cheltenham Festival at Cheltenham Racecourse offers something amazing all through the year. The unique Gold Cup in March to music and jazz festivals, the world’s oldest literature festival to world-class science, it has everything for us and gives 12 months of great experiences. The festival is also known as The Festival Town. Cheltenham is all about the 30+ annual festivals or significant events, which give the perfect opportunity for shared experiences and life-affirming moments with friends and family.
Once the spring season ended, Cheltenham became a melting pot of culture and imagination, commencing with the Cheltenham Jazz Festival. The festival has been hosted by the world’s renowned musicians Jamie Cullum, Van Morrison, Hugh Laurie, Imelda May, Stephane Grappelli, and Ornette Coleman. Cheltenham Festival of Performing Arts happens in May and was first established in 1926. There is a new addition to the festival known as the “Cheltenham International Film Festival”.
Summer in Cheltenham assures feel-good experiences. It lets you experience Cheltenham Balloon Fiesta, Cheltenham Food and Drink Festival, Wychwood Festival, Cheltenham Music Festival, and the esteemed 2000 Trees Festival. Suppose you wish to become a part of the popular events happening all around the year. In that case, booking your accommodation and festival tickets in advance is advised to avoid disappointment. The package and Cheltenham accommodation guide include hotels and self-catering options to match all budgets, from luxury hotels to country spa retreats, cozy guest houses, open self-catering apartments, and even local camps.
How to get to Cheltenham festival by Taxi
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Cheltenham Festival Dates And Address
1- The Cheltenham Festival -Horse Racing –
Location -Cheltenham
Date – 11 Mar 2025to14 Mar 2025 Open 10:30 –
Cheltenham Racecourse presents the pinnacle event on the jump racing calendar – The Cheltenham Festival 11 – 14 March 2025.
2- The Cheltenham Gold Cup – Horse Racing
Location -Cheltenham
Date – 14 Mar 2025Open 10:30 –
Be part of sporting history in 2025. Join us at Cheltenham Racecourse to celebrate 100-years of the Gold Cup. The pinnacle event of the jump-racing calendar.
3- Craft Festival Cheltenham -Crafts
Address-Imperial Square, Cheltenham
Date – 21 Mar 2025to23 Mar 2025
Meet the makers at Craft Festival Cheltenham, where 100 of the UK’s finest professional makers will exhibit, craft workshops for adults, craft demonstrations, and a host of free activities for children.
4- Fresh: Art Fair – Art-
Location – Cheltenham
Date : 3 Apr 2025 Open 17:30 – 21:00
4 Apr 2025 to 6 Apr 2025 Various Opening Times
Art Fair shows a broader range of art than any art fair outside London. From exciting new talent to famous names like Picasso, Banksy, Matisse and Miro this event brings you art from as little as £50 to £20,000 or more.
5- Cheltenham Wine Festival- Type -Festival
Address– Cheltenham
Date – 5 Apr 2025 -Various Opening Times
Join the Cheltenham Ladies College wine lovers to explore and taste many exciting wines at the Cheltenham Wine Festival. Enjoy your favorites and have fun discovering new ones from countries such as England, France, Italy,…
6- Cheltenham Observation Wheel- Type -Family
Address– Cheltenham
Date – 12 Apr 2025 to 5 May 2025 Open 12:00 – 21:00
Soar above Cheltenham on a spectacular observation wheel this Easter, offering breathtaking panoramic views from 12th April to 5th May.
7- The April Meeting- Type -Horse Racing
Address-Prestbury Park, Cheltenham
Date-16 Apr 2025to17 Apr 2025
It’s no easy task following the Cheltenham Festival; however, April’s two-day meeting is the perfect time to reflect on achievements and remember that racing, no matter the event, is competitive and above all else, a joyous occasion.
8- Cheltenham Jazz Festival- Type -Festival
Address– Cheltenham
Date – 30 Apr 2025 to 5 May 2025 Various Opening Times
Cheltenham, The Festival Town, is home to one of the country’s best-loved jazz festivals, attracting over 20,000 music fans annually. The popular annual event will take place 30 April – 5 May 2025.
9- Race Night ft. Hunter Chase Racing Type -Horse Racing
Address– Prestbury, Cheltenham
Date– 2 May 2025
The curtain comes down on the racing season with Cheltenham’s only evening fixture. The evening hosts a fun vibe from start to finish. You can feel the party atmosphere as soon as you walk through those gates onto the sacred grounds of Cheltenham…
10- Cheltenham Poetry Festival- Type -Festival
Address– Cheltenham
Date– 7 May 2025 to 17 May 2025 Various Opening Times
Cheltenham Poetry Festival offers an annual 10-day program of exciting live literature events each spring and a year-round online program of workshops and poetry lounges. The 2025 Cheltenham Poetry Festival will take place 7 – 17 May at venues…
11- Cheltenham Festival of Performing Arts- Type -Festival
Address– Cheltenham
Date-9 May 2025 to 17 May 2025
Cheltenham’s oldest festival was set up in 1926! The annual Cheltenham Festival of Performing Arts is packed with music, dance, and drama performances by children from local schools, theatre groups, dance schools, and music clubs.
12- Cotswold Festival of Steam- Type -Festival
Address– Cheltenham
Date-24 May 2025 to 26 May 2025 Open 09:00 – 17:00
Get ready to embark on a journey through time, where the past comes alive, and the heritage of steam locomotives is celebrated in all its glory. Join for a long bank holiday weekend filled with the magic of steam, picturesque landscapes, and the rich…
13- Cheltenham Fringe Festival- Type -Festival
Address– Cheltenham
Date-26 May 2025 to 1 June 2025
It is a festival celebrating various art, including music, theatre, film, drag, poetry, comedy, and more.
14- Gloucestershire Cheese Rolling on Coopers Hill- Type -Competition/Game
Address-Gloucester
Date– 26 May 2025O pen 12:00
The world-famous Gloucestershire Cheese Rolling returns on Monday, 26 May 2025, bringing thrilling action and quirky tradition back to Cooper’s Hill near Gloucester. Every year, thousands of spectators and daring competitors flock to this iconic…
15- Wychwood Festival- Type -Festival
Address– Cheltenham
Date– 30 May 2025 to 1 June 2025 Various Opening Times
Wychwood is an annual summer family festival that takes place at Cheltenham Racecourse. Nominated Best Family Festival at the UK Festival Awards, there is so much for all ages to enjoy and participate in. Wychwood Festival 2025 will take place 30 May…
14- Cheltenham Science Festival- Type -Festival
Address– Cheltenham
Date– 3 June 2025 to 8 June 2025
This popular annual festival brings together the UK’s most respected scientists, favorite science communicators, writers, and artists to discuss today’s hottest topics.
15- Cheltenham Running Festival Type -Running
Address– Evesham Road, Cheltenham
Date– 8 June 2025
This event offers you the unique opportunity to run a 5k, 10k or Half Marathon around the famous Cheltenham Racecourse!
16- Gloucestershire Warwickshire Railway Real Ale Festival Type- Railway / Train Events
Address– Cheltenham
Date-13 June 2025 to 15 June 2025 Open 09:00 – 17:00
Get ready for a journey back in time, where vintage locomotives and the finest brews come together in perfect harmony.
17- Cheltenham’s Three Peaks Challenge -Type- Event
Address– Cheltenham
Date– 14 June 2025 Open 06:30 – 18:30
The 22-mile walk, starting at their Charity ‘HQ’ in Lansdown Parade, allows you to take an exhausting but exhilarating adventure through Gloucestershire’s most picturesque landscapes.
18- Cheltenham Food & Drink Festival Type-Food and Drink
Address– Cheltenham
Date– 20 June 2025 to 22 June 2025
Pamper your palate and join family and friends over one great three-day weekend to celebrate the Cheltenham Food & Drink Festival. Enjoy live music, free wine-tasting talks, cheese tasting, artisan food producers, and many demonstrations…
19- Prescott Bike Fest Type- Motorsports
Address– Cheltenham
Date– 22 June 2025 Open 08:30 – 17:00
Prescott Bike Fest is THE one-stop-shop for bike lovers everywhere. Run the Hill entries, Paddock Specials, and the organisers’ Featured Club take to the world-famous Prescott Hill.
20- Cheltenham Music Festival Type- Festival
Address– Cheltenham
Date– 4 July 2025 to 12 July 2025
Cheltenham Music Festival brings eight performances and events by leading international artists, new talent and innovators.
21- 2000trees Festival Type- Festival
Address– Cheltenham
Date– 9 July 2025 to 12 July 2025
The multi-award-winning 2000trees festival is a three-day extravaganza set in the stunning Cotswold Hills. You’ll get three nights camping, a friendly, intimate atmosphere, amazing food, locally produced ciders, ales & lagers.
22- Cheltenham Cricket Festival Type- Sports
Address– Thirlestaine Road, Cheltenham
Date– 17 July 2025 to 5 Aug 2025
The Cheltenham Cricket Festival is one of the most loved events in the social and sporting calendar. The idyllic setting of Cheltenham College provides the perfect backdrop for cricket at the height of summer.
23- Cheltenham 7s Festival Type- Festival
Address– Cheltenham
Date-18 July 2025 to 19 July 2025
This is a festival for all sports lovers and festival-goers featuring a range of competitions for Rugby, Netball, Dodgeball, Fitness, and Juniors Rugb,y plus a huge line up of talented artists, bands, and DJs. The combination of sport and music is a
24- Fantasy Forest Festival at Sudeley Castle Type- Major Event
Address– Winchcombe
Date-18 July 2025to20 July 2025
Set within the stunning grounds of Sudeley Castle, Fantasy Forest Festival offers a unique, inclusive experience against the backdrop of one of the Cotswolds most magnificent family-friendly attractions.
25- Summer Jam: The Lakefest Warmup Type- Major Event
Address– Cheltenham
Date-25 July 2025to27 July 2025
The popular free music festival at The Brewery Quarter returns to kick start the summer holidays.
26- Cheltenham Heritage Open Days Type- Festival
Address– Cheltenham
Date– 12 Sept 2025 to 21 Sept 2025
10 days of Cheltenham heritage are free to explore! Discover Cheltenham and its heritage as buildings open their doors to the public with a complete program of exciting walks and fascinating talks.
27- Cheltenham International Film Festival Type- Festival
Address– Regent St, Cheltenham
Date– 19 Sept 2025 to 28 Sept 2025
Cheltenham International Film Festival has brought together filmmakers, guest celebrities, emerging talent, and audiences to celebrate the best in world cinema.
28- Run Cheltenham Type- Running
Address– Evesham Road, Cheltenham
Date– 21 Sept 2025
Run Cheltenham offers three incredible and unique racing experiences for all ages and abilities. All starting and finishing at Cheltenham Racecourse. From those wanting to experience running for the first time to the competitive athletes wanting to…
29- Cheltenham Literature Festival Type- Festival
Address-Cheltenham
Date– 10 Oct 2025to19 Oct 2025
Cheltenham Literature Festival, 10-19 October, promises a feast for the mind. As the world’s longest-running literature festival, the annual event leads the way in celebrating the written and spoken word, presenting the best new voices in fiction…
30- Cheltenham Literature Festival Free Events Type- Literature
Address-Cheltenham
Date– 10 Oct 2025 to 19 Oct 2025
More than one hundred free talks, performances, and workshops occur across the Festival’s ten days.
31- The Showcase Type- Horse Racing
Address-Cheltenham
Date– 24 Oct 2025 to 25 Oct 2025
The Showcase raises the curtain to the 2025/26 Cheltenham season. Once again, the thundering hooves, eager participants, and excited fans will return to the Home of Jump Racing on Friday, 24, and Saturday, 25 October 2025.
32- The November Meeting Type- Horse Racing
Address-Cheltenham
Date– 14 Nov 2025 to 16 Nov 2025
The November Meeting is an unmissable three-day Home of Jump Racing meeting. All roads lead to the Cheltenham Festival, but the magic starts at The November Meeting.
33- The Christmas Meeting Type- Horse Racing
Address-Cheltenham
Date– 12 Dec 2025 to 13 Dec 2025
Commence your Christmas celebrations at Cheltenham Racecourse over a weekend of top-quality racing on Friday, 12, and Saturday, 13 December. With the festive season about to enter the home straight, The Christmas Meeting brings joy and excitement for…
