Events

Explore our town 
Make memories and discover our unique mix of adventures, experiences and days out.

Half term at Hardwick Hall
Half term has never been more ‘love’ly! Step into an Elizabethan world of love and play through outdoor play and crafts.

Puffin' Billy
Head to Queen’s Park this February half term, feel the wind in your hair and wave to friendly faces as you ride around the park. 

Valentine's Canal Cruise
Soak up the love aboard the John Varley II, spotting moorhens, kingfishers and deer as you go.   

Chesterfield Festival of Cricket
Watch sell-out County Championship cricket, as well as vibrant Vitality Blast action at the height of summer.   

Socialise with friends and family
We have a lineup of events perfect for sharing together. And if you're planning to make a night of it, we’ve got plenty of ideas to help you enjoy the best the town has to offer.
Valentine's experiences to share 
Discover 8 ideas to make the most out of your Valentine's weekend, including Live music you’ll love and creative activities to bond over. 

Bottomless Brunch at Casa Hotel
Celebrate Valentine’s Day with a charcuterie board, sticky belly pork, stuffed peppers or patatas bravas and bottomless drinks of your choice…

Chesterfield Pride 
Join in one of the biggest and best-attended Pride events in the region for a day all about bringing the community together and having fun.   

Redbrik 10k
Take part in this weekend festival of running! Centred in the heart of Chesterfield, the 10k route takes you around our lovely town.   

Rail Ale Festival
Four days of fantastic entertainment, endless beers and ciders, the renowned Rail Ale Gin Palace and, of course, the Rail Ale trains.   

Explore our heritage
Whether you're looking to be entertained by shows at the theatre, or educated at local lectures, Chesterfield has a wide range of heritage days out you to enjoy.
Chesterfield Artisan Market
Browse stalls, taste the culinary treats, talk to artists, vintage dealers and designer-makers, or sample the hot authentic street food. 
Chesterfield Record Fair
Step back in time to your favourite gig with the authentic sound of vinyl at the Chesterfield Record Fair. 
Chesterfield 1940s Market
Featuring 40s music, street entertainment, a classic car & military vehicle display, and more. Take an immersive glimpse into the culture and character of the past.    

Canal Cruises
Relax with a Canal Cruise along the beautiful Chesterfield Canal on one of two tripboats – the John Varley II or the Madeline.   

Chatsworth Country Fair
See one of England’s most spectacular annual outdoor events with a unique blend of family entertainment, culinary inspiration, country pursuits and rural crafts.   

Filter events
Event Venue Dates Times
Canal Cruises Chesterfield Canal Mon 24 Aug 2026 Various
Puffin’ Billy Queen's Park, Boythorpe Road Tue 25 Aug 2026 – Fri 28 Aug 2026 10.30am – 4.00pm
Canal Cruises Chesterfield Canal Wed 26 Aug 2026 Various
Chesterfield Flea Market Chesterfield Market Place Thu 27 Aug 2026 9:00am – 4:00pm
Train running days at Barrow Hill Roundhouse Barrow Hill Roundhouse, Campbell Drive, Barrow Hill, Chesterfield, S43 2PR Sat 29 Aug 2026 – Sun 30 Aug 2026 10:00am – 4:00pm
Chesterfield Artisan Market Chesterfield Market, Main Square, S40 1AH Sun 30 Aug 2026 10:00am – 3:30pm
The 2026 Peak District Highland Games Matlock Farm Park, Jaggers Lane, Matlock, DE4 5LH Sun 30 Aug 2026 11:00am – 5:30pm
Canal Cruises Chesterfield Canal Mon 31 Aug 2026 Various
Puffin’ Billy Queen's Park, Boythorpe Road Tue 1 Sep 2026 – Fri 4 Sep 2026 10.30am – 4.00pm
Chesterfield Flea Market Chesterfield Market Place Thu 3 Sep 2026 9:00am – 4:00pm
Chatsworth Country Fair Chatsworth House, Bakewell, DE45 1PP Fri 4 Sep 2026 – Sun 6 Sep 2026 Various
Canal Cruises Chesterfield Canal Wed 9 Sep 2026 2:00pm – 4:00pm
Derbyshire Business Events co-founders at an Executive Networking Lunch.

Chesterfield Business Expo

The Chesterfield Business Expo is an exciting event for local companies to promote their business, raise brand awareness, increase sales and network.

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Derbyshire Business Hub: networking

Join Derbyshire Business Hub, a breakfast networking session hosted by East Midlands Chamber and Chesterfield Rotary.

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Frankie Valli Tribute starring Peter Andre at Chesterfield’s Winding Wheel Theatre.

The Very Best of Frankie Valli starring Peter Andre

The Very Best of Frankie Valli! Join Peter Andre in Frankie Valli tribute show a sensational tribute show talent.

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