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
Bottomless Brunch at Casa Hotel Casa Hotel, Lockoford Lane, S41 7JB Sat 18 Apr 2026 12:00PM – 6:00PM
Chesterfield Flea Market Chesterfield Market Place Thu 23 Apr 2026 09:00am – 4:00pm
Chesterfield Artisan Market Chesterfield Market, Main Square, S40 1AH Sun 26 Apr 2026 10:00am – 3:30pm
Chesterfield Flea Market Chesterfield Market Place Thu 30 Apr 2026 09:00am – 4:00pm
Canal Cruises Chesterfield Canal Fri 1 May 2026 1:00pm – 3:00pm
Bottomless Brunch at Casa Hotel Casa Hotel, Lockoford Lane, S41 7JB Sat 2 May 2026 12:00PM – 6:00PM
Canal Cruises Chesterfield Canal Mon 4 May 2026 Various
Chesterfield Flea Market Chesterfield Market Place Thu 7 May 2026 09:00am – 4:00pm
Chesterfield Record Fair Chesterfield Market Place Sun 10 May 2026 9.00am – 2:00pm
Canal Cruises Chesterfield Canal Wed 13 May 2026 7:00pm – 9:00pm
Chesterfield Flea Market Chesterfield Market Place Thu 14 May 2026 09:00am – 4:00pm
Rail Ale Festival Barrow Hill Roundhouse Railway Centre, Campbell Drive, Barrow Hill Chesterfield, S43 2PR Thu 14 May 2026 – Sun 17 May 2026 Various
Santa waving from balcony

Santa’s story time

Bring the little ones along to meet Santa in the cosy Tipi this festive season! Every Sunday afternoon, Santa will be sharing a story!

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Santa run in Queens Park Chesterfield

Chesterfield Santa Fun Run & Walk

Get into the festive spirit, dress up in a Santa suit and run around Queens Park at the Chesterfield Santa Fun Run!

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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.

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