Trips & Adventurous Activities in Cheltenham

Check out happening trips & adventurous activities events all around Cheltenham, EN

2000trees Music Festival 2026 - Thursday Tickets

 Thu, 09 Jul at 08:00 am Upcote Farm EUR 330

2000trees Music Festival 2026 - Friday Tickets

 Fri, 10 Jul at 08:00 am Upcote Farm EUR 328

The film Orchestra at Fantasy Forest Festival Sudeley 2026

 Sun, 19 Jul at 03:00 pm Sudeley Castle

The Princess Proms comes to Cheltenham 👸 TICKETS NOW ON SALE

 Sat, 04 Jul at 01:30 pm Everyman Theatre - Cheltenham

Alan Davies at Cheltenham Town Hall

 Mon, 28 Sep at 07:30 pm Cheltenham Town Hall

Steeleford Hill Climb 2026

 Sat, 08 Aug at 10:00 am Prescott Speed Hill Climb

Maisie Adam at Cheltenham Town Hall

 Tue, 20 Oct at 07:30 pm Cheltenham Town Hall

COTSWOLDS 100 SPORTIVE 2026

 Sat, 23 May at 07:30 am Cheltenham Racecourse

2026 Gentleman's Ride - Cheltenham, U.K.

 Sun, 17 May at 08:00 am Cheltenham Gloucestershire

Marchants Coach Trip - Three Counties Show, Malvern Showground

 Sat, 13 Jun at 08:15 am Marchant's

🎭✨ Illyria Theatre Night: The Three Musketeers

 Tue, 30 Jun at 07:45 pm Cheltenham Lido, Keynsham Road, GL537PU Cheltenham, United Kingdom

Peugeot Festival 2026

 Sun, 12 Jul at 08:00 am Prescott Speed Hill Climb

FREE group-led cycle rides

 Sat, 09 May at 02:00 pm Gloucestershire & Free

The Big Chill 25

 Sat, 24 Oct at 12:00 pm Cheltenham Lido, Keynsham Road, GL537PU Cheltenham, United Kingdom

Ride for Ryder 2026

 Sun, 12 Jul at 07:00 am Dean Close School

Matt Parker at Cheltenham Town Hall

 Sun, 04 Oct at 06:30 pm Cheltenham Town Hall

Adriana Brownlee - Death Zone

 Sat, 27 Jun at 07:30 pm Cheltenham Town Hall

Wellesbourne Market &/Or Stratford Upon Avon

 Sat, 23 May at 08:15 am Marchant's

Winchcombe Way Weekender - Day 1 -Western Loop - 21 miles

 Sat, 23 May at 08:00 am Winchcombe Long Stay car park, Back Ln, Winchcombe, Cheltenham, GL54 5PZ

Torquay or Paignton

 Thu, 07 May at 07:45 am Marchant's

Cheltenham Three Peaks Challenge 2026 for Aim Up

 Sat, 13 Jun at 06:30 am Cheltenham GBP 10 to 20

Cleeve Hill, Cheltenham Circular - Free Group Walk

Sun, 10 May at 11:00 am Cleeve Common

Brecon Beacons - Rail & Boat Trip

 Sun, 17 May at 07:50 am 61 Clarence Street, GL50 3LB Cheltenham, United Kingdom

Wellesbourne Market &/Or Stratford Upon Avon

 Sat, 27 Jun at 08:15 am Marchant's

Beyond Relaxation: A Yoga Nidra Immersion for teachers and therapists with Dina Cohen

 Sat, 06 Jun at 10:00 am Orangeyoga Studio

Winchcombe Way Weekender - Day 2- Eastern Loop - 21 miles

 Sun, 24 May at 08:00 am Winchcombe Long Stay car park, Back Ln, Winchcombe, Cheltenham, GL54 5PZ

Belmont Saturday stay and play for families with children with send needs

 Sat, 09 May at 12:00 pm Belmont School Free

Brecon Beacons - Rail & Boat Trip

 Sun, 23 Aug at 07:50 am 61 Clarence Street, GL50 3LB Cheltenham, United Kingdom

The Fab Libs: Any Scene Will Do

 Wed, 27 May at 07:30 pm Cheltenham Playhouse, 47-53 Bath Road, GL53 7HG Cheltenham, United Kingdom

Introduction to Trail Running - week 5

 Wed, 10 Jun at 06:30 pm Cheltenham Racecourse

Seas The Day: Jessica Rowe & Miriam Payne

 Thu, 18 Jun at 07:00 pm 47-53 Bath Road, GL53 7HG Cheltenham, United Kingdom

Royal Air Force Museum Hendon, London

 Thu, 28 May at 07:15 am 61 Clarence Street, GL50 3LB Cheltenham, United Kingdom

Muscles in Focus with Ian Davis

 Sat, 11 Jul at 09:00 am Orangeyoga Studio

Riders and Striders - A Cleeve Hill Circuit

 Thu, 27 Aug at 10:00 am Cleeve Hill Golf Club Free

Yoga in Tuscany - a 2-PART adventure! EARLY BIRD BOOKING DISCOUNT!

 Sat, 29 Aug at 12:00 pm Living Yoga Holidays

Off-Road Training Session

 Tue, 14 Apr at 06:00 pm Pittviell Park cx course, Tommy Taylors Lane GBP 7