Events

Explore this Christmas 
Make memories and discover our unique mix of adventuresexperiences and days out.
Ride on our merry Puffin' Billy
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 10 Sep 2026 8:30am – 10:30am
Canal Cruises Chesterfield Canal Fri 11 Sep 2026 1:00pm – 3:00pm
Chesterfield Record Fair Chesterfield Market Place Sun 13 Sep 2026 9.00am – 2:00pm
Canal Cruises Chesterfield Canal Wed 16 Sep 2026 7:00pm – 9:00pm
Chesterfield Flea Market Chesterfield Market Place Thu 17 Sep 2026 9:00am – 4:00pm
Canal Cruises Chesterfield Canal Fri 18 Sep 2026 2:00pm – 4:00pm
Canal Cruises Chesterfield Canal Wed 23 Sep 2026 2:00pm – 4:00pm
Chesterfield Flea Market Chesterfield Market Place Thu 24 Sep 2026 9:00am – 4:00pm
Canal Cruises Chesterfield Canal Fri 25 Sep 2026 1:00pm – 3:00pm
Chesterfield Artisan Market Chesterfield Market, Main Square, S40 1AH Sun 27 Sep 2026 10:00am – 3:30pm
Canal Cruises Chesterfield Canal Sun 27 Sep 2026 10:00am – 4:00pm
Canal Cruises Chesterfield Canal Wed 30 Sep 2026 2:00pm – 4:00pm

Director Development Programme

The Director Development Programme is designed to support directors or senior managers within businesses to support and grow their business or the department they lead.

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Chesterfield Market

Chesterfield Flea Market

Rummage through an eclectic mix at the popular Chesterfield Flea Market.

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Chesterfield Record Fair

Are you a collector of records? If so, head to this monthly outdoor Record Fair on Chesterfield Market to browse a range of stalls. 

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