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
Christmas street entertainment Chesterfield Town Centre Sat 20 Dec 2025 12:00pm – 3.30pm
Santa Special Cruises Chesterfield Canal - Tapton Lock and Hollingwood Hub Sat 20 Dec 2025 – Sun 21 Dec 2025 Various
Santa Special Cruises Chesterfield Canal - Tapton Lock and Hollingwood Hub Sat 20 Dec 2025 – Tue 23 Dec 2025 Various
Puffin’ Billy Queen's Park, Boythorpe Road Sat 20 Dec 2025 – Sun 21 Dec 2025 10.30am – 4.00pm
Chesterfield Artisan Market Chesterfield Market, Main Square, S40 1AH Sun 21 Dec 2025 10:00am – 3:30pm
Santa’s story time Chesterfield Market Place, Chesterfield, S40 1AR Sun 21 Dec 2025 3:30pm – 4:00pm
Chesterfield Santa Fun Run & Walk Queen's Park, Chesterfield Sun 21 Dec 2025 Various
Christmas street entertainment Chesterfield Town Centre Mon 22 Dec 2025 12:00pm – 3.30pm
Christmas street entertainment Chesterfield Town Centre Tue 23 Dec 2025 12:00pm – 3.30pm
Chesterfield Pantomime – Jack and the Beanstalk Winding Wheel Theatre Fri 26 Dec 2025 – Wed 31 Dec 2025 –
Canal Cruises Chesterfield Canal Thu 1 Jan 2026 Various
Chesterfield Pantomime – Jack and the Beanstalk Winding Wheel Theatre Fri 2 Jan 2026 – Sun 4 Jan 2026 –
Image of a shop window decorated for the the Robin's Lost Letters Winter Trail
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Winter Window Trail

Following on from the success of last year, the Winter Window trail is back with to bring a touch of festive magic to Chesterfield!

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Christmas street entertainment

As part of Christmas in Chesterfield, Chesterfield Borough Council has arranged a variety of different entertainment for the town centre.

Read more >
Christmas at Hardwick
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Hardwick Wintertide

Come back and build memories at Hardwick once again as the season of Elizabethan magic will be here for Hardwick Wintertide!

Read more >