Things to do in Cheltenham

Things To Do in Cheltenham, Gloucestershire

Green Spaces & Local Walks

Cheltenham is often referred to as the Gateway to the Cotswolds and has plenty of open space to enjoy - Pittville Park is a local favourite with lakes, boat hire, and a well-kept playground. Sandford Park is great for a quiet stroll, and Cleeve Hill, just outside town, offers far-reaching views and good walking routes across the Cotswolds.

Food, Drink & Cafés

From local brunch spots to evening meals out, Cheltenham has a solid mix of independent places and well-known names. Head to the Montpellier area or The Suffolks for coffee shops, wine bars, and laid-back restaurants - or visit the Dunkertons Cider site nearby, which now has a great mix of food traders and a shop selling local produce.

Festivals & Culture

Cheltenham’s calendar is packed, but not overwhelming. It’s best known for the Literature, Science, and Jazz Festivals, plus the Cheltenham Races if that’s your thing. There’s also live music at the Town Hall, film and theatre at the Everyman, and a good choice of local galleries and smaller venues too.

Shopping & Everyday Essentials

Cheltenham has all the main high street shops, supermarkets, and retail parks you’d expect. John Lewis, M&S, and Whole Foods (at Gallagher Retail Park) are all nearby, along with essentials like GP surgeries, pharmacies, and dentists. The town centre is walkable, well connected by bus, and easy to get around.

Schools & Education

There’s a strong choice of both state and independent schools in Cheltenham. Local standouts include Pate’s Grammar, Balcarras School, and Cheltenham College - all regularly ranked among the top in the region. There’s also a large campus for Gloucestershire College, and the University of Gloucestershire has multiple buildings across town.

Connections & Travel

Cheltenham is well linked by road and rail. Direct trains to London Paddington take around 2 hours, and there are regular connections to Bristol, Birmingham, and Swindon. The M5 and A40 are easily accessed, and Gloucestershire Airport is just outside town for private or short-haul flights.

More Things to Do Near Cheltenham

• Broadway Tower – One of the Cotswolds’ most iconic viewpoints, with walking trails, a café, and panoramic views stretching to Wales on clear days.
• The Cotswold Way – A long-distance walking route running through nearby hills, ideal for weekend walks or shorter scenic sections around Cleeve Hill.
• Tewkesbury Abbey – A stunning medieval church and riverside town packed with heritage, independent shops, and riverside pubs - just 25 minutes away.
• Cotswold Farm Park – A great option for families, offering seasonal activities, rare breed animals, and farm-to-fork food options.
• Cirencester – Known as the ‘Capital of the Cotswolds’, with its Roman museum, busy market square, and growing food scene.

If you're thinking about life at Willowside Grange, Cheltenham puts a wide mix of things within easy reach - from green space and historic landmarks to everyday shops, schools, and events. Whether it's a Sunday walk, a night at the theatre, or simply a good coffee on your day off, living here gives you plenty of ways to make the most of the area.