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 Tipi Christmas Chesterfield Market Place, Chesterfield, S40 1AR Fri 7 Nov 2025 – Wed 31 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
Canal Cruises Chesterfield Canal Thu 1 Jan 2026 Various
Chesterfield Artisan Market Chesterfield Market, Main Square, S40 1AH Sun 25 Jan 2026 10:00am – 3:30pm
Chesterfield Artisan Market Chesterfield Market, Main Square, S40 1AH Sun 22 Feb 2026 10:00am – 3:30pm
Chesterfield Artisan Market Chesterfield Market, Main Square, S40 1AH Sun 29 Mar 2026 10:00am – 3:30pm
Canal Cruises Chesterfield Canal Sat 4 Apr 2026 – Sat 20 Jun 2026 Various
Canal Cruises Chesterfield Canal Mon 6 Apr 2026 Various
Canal Cruises Chesterfield Canal Wed 8 Apr 2026 Various
Canal Cruises Chesterfield Canal Sun 12 Apr 2026 – Sun 24 May 2026 Various
Chesterfield Artisan Market Chesterfield Market, Main Square, S40 1AH Sun 26 Apr 2026 10:00am – 3:30pm
Chesterfield Tipi Christmas
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Chesterfield Tipi Christmas

Find the perfect escape during the festive season with seasonal food and drink inside Chesterfield Tipi Christmas.

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Puffin Billy at Queen's Park
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Puffin' Billy

Hop aboard Puffin' Billy. Feel the wind in your hair and wave to friendly faces as you ride around the park.

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Chesterfield Artisan Market

Chesterfield Artisan Market takes place on the last Sunday of the month and features over 80 of the very finest artisan traders.

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