Events

Explore this Christmas 
Make memories and discover our unique mix of adventures, experiences and days out.
Ride on our merry Puffin' Billy
Santa’s hopping on the much-loved miniature train at Queen’s Park. 

Festive street entertainment  
Keep an eye out for juggling elves, mischievous penguins, singing crackers AND a life-sized polar bear. What's on this week?
Chesterfield Pantomime - Jack and the Beanstalk
The magical pantomime is coming to the Winding Wheel Theatre this December, and it’s a towering tale your whole family will love. 

Winter Window Trails
How many baubles can you spot in our shop windows across town? A fun activity to enjoy together. 

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

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.
Santa Fun Run 
Participate in our annual Santa Fun Run and Walk by dressing up as Santa and raising funds for Ashgate Hospice. 

Festive Bottomless Brunch at Casa
Delicious sharing platters of charcuterie and tapas with 90 mins of bottomless drinks. Perfect recipe for a great time together with friends or loved ones.
Visit Tipi Christmas 
Meet friends and family in our cosy tipi for hot chocolate, mulled wine, and seasonal treats by the fire. 

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. 
Hardwick Wintertide
Experience the festive spirit at Hardwick Hall, where twinkling lights illuminate the historic mansion. 

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.    

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
Chesterfield Flea Market Chesterfield Market Place Thu 8 Jan 2026 09:00am – 4:00pm
Derbyshire Business Hub: networking East Midlands Chamber, Commerce House, Millennium Way, Dunston Road, Chesterfield, S41 8ND Thu 8 Jan 2026 8:30am – 10:30am
Chesterfield Record Fair Chesterfield Market Place Sun 11 Jan 2026 9:00am – 2:00pm
Chesterfield Flea Market Chesterfield Market Place Thu 15 Jan 2026 09:00am – 4:00pm
Champions Round Table: Skills, apprenticeships and careers Chesterfield College Thu 15 Jan 2026 2:00pm – 4:00pm
Smartphone Success on Social Media – The Video Formula Dunston Innovation Centre, Dunston Road, Chesterfield, S41 8NG Wed 21 Jan 2026 10:00am – 12:30pm
Chesterfield Champion event: Annual Consultation Ringwood Hall Hotel & Spa Wed 21 Jan 2026 8:00am – 10:00am
Chesterfield Flea Market Chesterfield Market Place Thu 22 Jan 2026 09:00am – 4:00pm
Bottomless Brunch at Casa Hotel Casa Hotel, Lockoford Lane, S41 7JB Sat 24 Jan 2026 12:00PM – 6:00PM
Chesterfield Artisan Market Chesterfield Market, Main Square, S40 1AH Sun 25 Jan 2026 10:00am – 3:30pm
Personal effectiveness using the power of insights discovery East Midlands Chamber, Chesterfield, S41 8ND Wed 28 Jan 2026 9:30am – 4:30pm
Chesterfield Flea Market Chesterfield Market Place Thu 29 Jan 2026 09:00am – 4:00pm
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Chesterfield Pantomime - Jack and the Beanstalk

Climb into a world of festive fun with this year’s Chesterfield Pantomime: Jack and the Beanstalk! A mighty beanstalk launches Jack into an epic adventure, and you’re invited to join the magic. Featuring a star-studded cast, including Jamie Christian, aka the duelling Giant from Gladiators.

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Children holding present with man dressed as an elf at Matlock Farm Park
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Christmas fun at Matlock Farm Park

Join in with a variety of Christmas fun at Matlock Farm Park, featuring a Santa's Grotto, Breakfast with Santa and more!

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Children holding present with man dressed as an elf at Matlock Farm Park
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Christmas fun at Matlock Farm Park

Join in with a variety of Christmas fun at Matlock Farm Park, featuring a Santa's Grotto, Breakfast with Santa and more!

Read more >