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. 

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.
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. 

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

Brampton Brewery Tour
This tour brings to life the brewery’s history, explains the brewing process, and the chance to taste Brampton Brewery's award-winning beer. 
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.
Train running day at Barrow Hill Roundhouse
Discover one of the largest collections of diesel, electric, and steam locomotives in the country at the final train running day of 2025. 

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. 
Filter events
Event Venue Dates Times
Derbyshire Business Hub: networking East Midlands Chamber, Commerce House, Millennium Way, Dunston Road, Chesterfield, S41 8ND Thu 14 May 2026 8:30am – 10:30am
Canal Cruises Chesterfield Canal Fri 15 May 2026 2:00pm – 4:00pm
Redbrik Foundation Chesterfield 10K Chesterfield Town Centre Sun 17 May 2026 10.00am –
Canal Cruises Chesterfield Canal Wed 20 May 2026 2:00pm – 4:00pm
Chesterfield Flea Market Chesterfield Market Place Thu 21 May 2026 09:00am – 4:00pm
Canal Cruises Chesterfield Canal Fri 22 May 2026 1:00pm – 3:00pm
Canal Cruises Chesterfield Canal Mon 25 May 2026 Various
Canal Cruises Chesterfield Canal Wed 27 May 2026 Various
Chesterfield Flea Market Chesterfield Market Place Thu 28 May 2026 9:00am – 4:00pm
Chesterfield 1940s Market Town Centre, Chesterfield, Derbyshire, S40 1PB Thu 28 May 2026 10am – 4pm
Canal Cruises Chesterfield Canal Fri 29 May 2026 1:00pm – 3:00pm
Chesterfield Artisan Market Chesterfield Market, Main Square, S40 1AH Sun 31 May 2026 10:00am – 3:30pm

Christmas street entertainment

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

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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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Woman on blue trip boat on Chesterfield Canal with red trip boat ahead

Canal Cruises

Relax with a Canal Cruise along the beautiful Chesterfield Canal on the John Varley II or Madeline. These are the two trip boats that run in Chesterfield.

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