It's time to shake off those winter blues and start looking after our mental and physical wellbeing. We've rounded up organised runs, treks, bike rides and wellbeing events taking place in and around Cheltenham in 2026 that are guaranteed to help you feel your best!
Best organised runs taking place in Cheltenham
Cheltenham Parkrun & Junior Parkrun
Not only is running great for cardiovascular health, but it can have an incredible impact on your mental wellbeing, lowering cortisol levels while promoting clarity and a peaceful mind.
Parkrun Cheltenham is a free, fun and friendly weekly event, providing a positive and inclusive atmosphere where there's no time limit and no one finishes last. You can walk, jog, run, volunteer, spectate or just join in for the post-run coffee.
Adults run a 5km course around Pittville Park, and junior runners (aged 4–14 years) also have the opportunity to get outdoors and run a free 2km race at the Park Campus.
When: 9am Saturdays (adults) / 9am Sundays (juniors)
Where: Pittville Park, Cheltenham GL50 4SH / The Park, Cheltenham GL50 2RH
More details: Cheltenham Parkrun / Cheltenham Junior Parkrun
Run Cheltenham
Looking to step up your weekly Parkrun to something a bit more demanding? Run Cheltenham is the sporting challenge for you. This annual event offers a series of closed-road races that are fun and engaging experiences for people of all ages and abilities.
There are three races to choose from on the same day, all starting and finishing at Cheltenham Racecourse. The 13.1-mile Cheltenham Half Marathon takes you past Cheltenham sights like the Pittville Pump Room, Town Hall and Montpellier Gardens.
The Cheltenham 10k is for runners who want to experience the best of the Regency town in a shorter distance. Or the Move More Mile is the perfect introductory distance of one mile for first-time runners and families.
When: Sunday 20 September 2026
Where: Cheltenham Racecourse
More details: Run Cheltenham
Cheltenham Running Festival
This event offers the opportunity to run a chip-timed 5k, 10k or Half Marathon around the famous Cheltenham Racecourse in support of The RunThrough Foundation. This year there's also a kids' race, making this a fun day out for the whole family!
Unlike the Run Cheltenham event, the route purely follows the Cheltenham Racecourse track. Each mile is accurately marked, with plenty of helpers to keep you (quite literally) on track and encourage you to the finish line.
When: Sunday 14 June 2026
Where: Cheltenham Racecourse
More details: Cheltenham Running Festival
Race for Life Cheltenham
There's another chance to take on the iconic Cheltenham Racecourse circuit this summer while raising money for Cancer Research UK's life-saving battle against cancer at the Race for Life Cheltenham.
The event has a choice of different events over the same weekend so everyone can take part. Go for a new PB in the 5km or 10km races. Or climb, crawl and slide your way around the Pretty Muddy obstacle course at your own pace – with versions for both adults and kids aged 6–12 years.
When: Saturday 27 and Sunday 28 June 2026
Where: Cheltenham Racecourse
More details: Race For Life Cheltenham
Recommended bike rides in Cheltenham and the Cotswolds
Cotswolds 100 Sportive
Prefer the feel of cycling shoes to running trainers? The Cotswolds 100 Sportive has got you covered. There are two ride lengths to choose from – 166 km (101 miles) and 104 km (64 miles).
The route starts at Cheltenham Racecourse and heads out into the stunning Cotswolds Area of Outstanding Natural Beauty. It's designed as a relaxed, enjoyable day in the saddle rather than a punishing challenge. Whether you’re riding solo or with friends, it’s a great chance to soak up the scenery and simply enjoy being on your bike.
When: Saturday 23 May 2026
Where: Cheltenham Racecourse
More details: Cotswolds 100 Sportive
Ride For Ryder – The Sportive 2026
Our local charity, Sue Ryder Care at Leckhampton Court Hospice, invites cyclists to get on their bikes for Ride for Ryder – The Sportive 2026. One of the longest-running and best-loved charity cycling events in the Cotswolds, there are five beautiful routes to choose from, ranging from 40km to 160km, offering options for all abilities.
Enjoy some of the most stunning routes the countryside has to offer while raising vital funds for local families needing expert and compassionate care.
When: Sunday 12 July 2026
Where: Dean Close School, Cheltenham GL51 6HE
More details: Ride For Ryder
Cheltenham Tri Festival 2026
There's another chance to raise much-needed funds for charity as you swim, run and cycle your way around the Cheltenham Tri Festival, run jointly by Sue Ryder and Cheltenham Lido.
With a choice of distances, the event is suitable all abilities and fitness levels, from complete novices to pro triathletes. After a swim in the lido's outdoor pool, competitors tackle running and cycling routes around Sandford Park and across Cheltenham for an all-round challenge.
When: Sunday 13 September 2026
Where: Cheltenham Lido, Cheltenham GL53 7PU
More details: Cheltenham Tri Festival
Charity treks around Cheltenham
Cheltenham's Three Peaks Challenge
Prefer a slower pace to soak in the beauty around you? We have just the event! The annual Cheltenham's Three Peaks Challenge is a one-day 30km trek across Cleeve Hill, Leckhampton Hill and Crickley Hill, organised by and in aid of Aim Up.
It's a fabulous way to raise money for a worthwhile local charity whilst experiencing the glorious countryside on our doorstep. You can enjoy this adventure safe in the knowledge you are on a fully recced 22-mile route with markers to guide you, and volunteers to point you in the right direction.
When: Saturday 13 June 2026
Where: Well Close House, Lansdown Parade, Cheltenham GL50 2LH
More details: Cheltenham's Three Peaks Challenge
Trek26 Cotswolds
Another opportunity to experience an adventure in the Cotswolds whilst raising money for charity and boosting your fitness is Trek26 Cotswolds. Join the Alzheimer's Society for an epic 13- or 26-mile trek through ancient woodlands, wildflower meadows and historic Cotswold stone villages.
Both routes start and finish at Postlip Farm just outside Cheltenham. After passing under the bridges of the Gloucestershire–Warwickshire Steam Railway and through picturesque Gotherington, your climb up to Cleeve Hill – with the longer route continuing along stretches of the Winchcombe Way and Cotswold Way.
When: Saturday 11 July 2026
Where: Postlip Farm, Cheltenham GL54 5AQ
More details: Trek26 Cotswolds
Yoga and wellbeing events in and around Cheltenham
Cotswold wellbeing retreats
The Cotswold Wellbeing Retreats at Notgrove Holidays are designed to nourish, awaken, heal and renew. The idyllic 1,500-acre private Notgrove Estate in the beautiful Cotswold countryside is the perfect place to reflect and unwind from the stresses and strains of everyday life.
Their two-night/three-day retreats take place several times a year and include seasonal yoga, guided meditation, forest bathing, nourishing local food and accommodation in Notgrove's cosy glamping pods.
When: Spring weekend retreat: 10 – 12 April 2026. Autumn weekend retreat: 11 – 13 September 2026
Where: Notgrove Estate, Gloucestershire GL54 3BT
More details: Cotswold Yoga Retreat and Wellbeing Holiday
Discover more ways to make the most of 2026 with our New Year, New Adventures.
