Cheltenham’s not just about festivals and fine buildings—it’s a town made for exploring. Whether you’re here for the weekend or you’ve lived in Charlton Kings for a decade, there’s always something new to do. From green parks to adrenaline activities, culture spots to spontaneous nights out, there’s more variety than you might expect. Add in
Groupon vouchers, deals and limited-time offers, and it becomes even easier to make the most of your time in town.
Explore Cheltenham Through Experiences
Sightseeing doesn’t always mean standing still. Cheltenham’s walkability and compact layout mean you can cover a lot without ever needing to rush. For those who enjoy a deeper look into local history, quirky tours or mini-adventures, options are surprisingly varied.
- Discover stories behind Regency architecture with a self-guided heritage trail
- Take in the art and sculpture across Montpellier and The Promenade
- Browse experience vouchers that bundle walking tours or local food tastings
Local tip: The Suffolks has hidden gems for boutique shopping and cafes—perfect mid-walk stops.
Hands-On Fun and Rainy Day Wins
Let’s face it—Cotswolds weather isn’t always reliable. But Cheltenham comes prepared. Indoor options range from active fun to creative workshops, with many venues offering
discounted sessions midweek or during school holidays.
- Test your teamwork with escape room deals near The Brewery Quarter
- Try your hand at clay sculpting or painting at community studios in Pittville
- Enjoy classic ten-pin bowling or VR gaming near Swindon Road
Great for families, groups, or solo days when you just want to try something new.
Get Outdoors: Parks, Paddleboards and Scenic Routes
One of Cheltenham’s biggest strengths? The green space. Whether you’re walking through Pittville Park or venturing a little outside the town centre, there’s no shortage of fresh air and open paths.
- Join a paddleboarding session on the River Chelt or explore nearby trails toward Leckhampton Hill
- Stroll through Pittville’s lakes and gardens or cycle the Honeybourne Line path
- Find local activity deals for guided hikes or group outdoor fitness
And when it’s sunny, even a picnic on Montpellier Gardens’ lawns feels like an event.
Cultural Highlights and Off-the-Radar Gems
Cheltenham might be known for its literature and jazz festivals, but culture here goes well beyond the seasonal headline acts. Small galleries, local performances, and community events fill in the rest of the calendar.
- Catch intimate shows at Cheltenham Playhouse or Parabola Arts Centre
- Visit The Wilson for exhibitions that cover everything from local history to contemporary art
- Look for museum discounts and art workshops tied to current displays
Not everything here needs to be high-brow to be rewarding—and that’s part of the charm.
Weekend Events and Where to Find Them
Cheltenham shines at the weekend. Whether you're in Lansdown or near Bath Road, there’s usually something happening nearby—from pop-up food festivals to live music in tucked-away venues.
- Check event and festival offers for ticketed options
- Explore artisan markets near Montpellier Walk or street performances on High Street
- Visit local breweries or wine-tasting evenings happening in The Suffolks
Keep an eye on community boards and social feeds—you'll often find something you didn’t even know existed.
Leisure for All Ages (Yes, Even Teens)
Cheltenham does well at providing balanced options for families, especially when kids range in age. You’ll find experiences that work just as well for adults as they do for teens or younger children.
- Play mini golf or explore Pittville Pump Room’s historical displays
- Book family deals for cinema tickets at Cineworld or the Everyman Theatre
- Try local sports centres in Hatherley for badminton, indoor climbing or swimming
Many places offer
family bundles and 2-for-1 entry offers—especially during off-peak hours.
Unwind with Evening Entertainment
After a day of exploring, Cheltenham offers a surprisingly relaxed but vibrant evening scene. Whether you’re up for live performance or just a casual evening with friends, there are options that don’t require a reservation or a dress code.
- See a play, film or comedy act using theatre and show deals
- Find live jazz in pubs around Bath Road or acoustic sets in Montpellier wine bars
- Grab late-night eats and local cider at pop-up stalls in Brewery Quarter
Not everything needs to be planned—some of the best nights out in Cheltenham are the ones you stumble into.
