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Top Things to Do in Chester for Fun and Relaxation

Chester is one of those cities that rewards slowing down and looking closer. From the Roman walls to the riverside paths and timbered high streets, it blends history with a modern spirit of adventure. Whether you’re walking the Rows, punting down the Dee, or exploring a tucked-away café in Hoole, there’s always something to do—and plenty of ways to enjoy it without spending a fortune. With regular Groupon deals, discounts, and activity vouchers around the city, trying something new in Chester is both easy and affordable.

Active Days in and Around the City

Chester’s compact size makes it a perfect place for active exploration. You can start your day with a peaceful run along the River Dee, pass beneath the Old Dee Bridge, and end up at Grosvenor Park for a coffee under the trees. Kayaking and paddleboarding are increasingly popular along the riverbanks, with instructors offering small-group sessions or one-to-one coaching for beginners. If you prefer solid ground, consider heading to the Meadows for open space and informal games, or venture just a bit further to Delamere Forest for hiking and trail cycling. You’ll also find activity vouchers in Chester for:
  • Paddleboarding and kayaking on the Dee
  • Outdoor fitness classes near Handbridge and Grosvenor Park
  • Climbing and indoor sports just outside the city centre

Local Culture You Can Really Engage With

Chester’s history is its backbone, but there’s much more happening beneath the surface. Beyond the cathedral and amphitheatre, the city hosts fringe theatre, art exhibitions, and spoken-word nights that bring fresh energy to old streets. Alexander’s Live is a local favourite for intimate gigs, while Storyhouse combines a theatre, cinema, and cultural hub all under one roof. Check their schedule regularly—there are often theatre and live performance deals to take advantage of. For something quieter, the Grosvenor Museum or the Watergate Street Gallery offer exhibitions that surprise and educate without demanding hours of your time. Many events are walk-in or donation-based, especially during off-peak seasons.

Where to Go on the Weekend

Weekends in Chester are made for wandering. The Rows are always buzzing, especially with weekend markets and pop-up food stalls. Live music filters out from cafés and pubs in Boughton, while community events are often tucked into Grosvenor Precinct or the Garden Quarter. Keep an eye out for seasonal happenings in Town Hall Square, from local makers' markets to city-wide food festivals. Check out festival and event vouchers for:
  • Street food weekends and artisan pop-ups
  • Music and storytelling festivals across the city centre
  • Workshops in Hoole and independent market stalls along Watergate Street
The best experiences here tend to feel local, laid-back and surprisingly affordable.

Family-Friendly Without the Fuss

Chester is a brilliant family city. Compact and walkable, it’s full of low-stress activities that work for a wide range of ages. Start with a river cruise or hop on the miniature railway at Grosvenor Park. On a rainy day, Storyhouse offers children’s cinema screenings and relaxed library corners, while the city’s Roman Tours provide fun, costumed history walks that get kids involved. You’ll find soft play, wildlife experiences, and even alpaca walks in the nearby countryside. Plan smart with cinema deals in Chester or use family passes for museums and activity centres.

Rethink How You See Chester

Even locals admit there are sides of Chester they haven’t explored. A guided walking tour will show you what’s hiding in plain sight—from hidden courtyards to old trade routes and haunted basements. Or, if you’re more of an independent explorer, book a themed trail or rent a rowing boat and make your way through Chester from the water. You can also browse sightseeing vouchers for:
  • History walks and ghost tours through the Rows
  • Boat cruises and wildlife spotting along the Dee
  • Food tours through Chester Market and the independent café scene
It’s a city that reveals itself layer by layer—the more you explore, the more rewarding it becomes.