Events

Explore our town 
Make memories and discover our unique mix of adventures, experiences and days out.

Ashgate Hospice Superhero Night Walk
Grab your cape and mask. Chesterfield’s superheroes are marching through Queen’s Park in this brilliant fundraising opportunity for the whole family.   

Chesterfield Fireworks
Bonfire Night is on the way! Get together under the incredible bursts of colour for a family-oriented evening of sparkling entertainment.   

Sanctuary of Light
Be immersed in light and sound at the Sanctuary of Light show, which returns to Chesterfield's iconic Crooked Spire. 

Bolsover Lantern Parade
Join the Bolsover Lantern Parade, one of the UK's biggest and longest-running light processions. 

Bright Winter Nights
Experience an immersive feast for the senses at Bright Winter Nights, coming to Bolsover Castle. 

Festival of Christmas Trees
Chesterfield's iconic Crooked Spire church will be filled with uniquely decorated Christmas trees once again this festive season. 

Santa Special Cruises
Santa Claus will be jumping on board two of Chesterfield Canal's most legendary vessels this Christmas season. 

Train running days 
All aboard for a train ride along the Springwell branch line at one of Barrow Hill Roundhouse’s special train running days.
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.
Tipi Christmas
The magical Tipi Christmas returns to our town centre for 2026, offering a cosy retreat filled with rustic festive charm. 

Amuzin Stand-Up Comedy
Ready for a good laugh? See stand-up comedians from around the country as they come to our town centre for the night. 

Daniel O'Reilly - Let's Have It
After gaining millions of followers online, Daniel O’Reilly has taken his comedy on tour around the UK. Next up, he’s bringing his show, Let’s Have It, to Chesterfield. 

Brewery Tour
Discover the story behind Brampton Brewery, learn how its award-winning beers are crafted, and taste a selection of flavoursome ales during expert talks. 

Casa Bottomless Brunch 
Indulge together with a charcuterie board, sticky belly pork, stuffed peppers or patatas bravas and bottomless drinks of your choice…
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. 
Chesterfield Record Fair
Step back in time to your favourite gig with the authentic sound of vinyl at the Chesterfield Record Fair. 
Canal Cruises
Relax with a Canal Cruise along the beautiful Chesterfield Canal on one of two tripboats – the John Varley II or the Madeline.   

Filter events
Event Venue Dates Times
Canal Cruises Chesterfield Canal Sun 4 Oct 2026 – Sun 25 Oct 2026 Various
Bottomless Brunch at Casa Hotel Casa Hotel, Lockoford Lane, S41 7JB Sat 17 Oct 2026 Various
Paddlesports on Chesterfield Canal Hollingwood Hub, 22 Works Road, Hollingwood, S43 2PF Sat 17 Oct 2026 – Sun 18 Oct 2026 Various
Crooked Spire Tower Tours The Parish Church of St Mary and All Saints, Church Way, Chesterfield S40 1XJ Sat 17 Oct 2026 2.30pm – 3.30pm
Ashgate Hospice Superhero Night Walk Queen's Park, Boythorpe Rd, Chesterfield S40 2ND Sat 17 Oct 2026 Various
Chesterfield Business Awards – Autumn Networking Social Armisteads, 22-24 Corporation St, S41 7TP Thu 22 Oct 2026 5:30pm – 7.30pm
Chesterfield Flea Market Chesterfield Market Place Thu 22 Oct 2026 9:00am – 4:00pm
Derbyshire Manufacturing Network Penny Engineering Limited, Clowne, Chesterfield, S43 4AB Fri 23 Oct 2026 07:30am – 10:30am
Chesterfield Observatory Hastings Close, Chesterfield, Derbyshire S41 8RH Fri 23 Oct 2026 8:00pm – 10:00pm
Crooked Spire Tower Tours The Parish Church of St Mary and All Saints, Church Way, Chesterfield S40 1XJ Fri 23 Oct 2026 – Sat 24 Oct 2026 2.30pm – 3.30pm
Disco For Grown Ups Winding Wheel Theatre, 13 Holywell St, Chesterfield S41 7SA Fri 23 Oct 2026 7:30pm – 11:00pm
Paddlesports on Chesterfield Canal Hollingwood Hub, 22 Works Road, Hollingwood, S43 2PF Sat 24 Oct 2026 – Sun 25 Oct 2026 Various
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.

Read more >
Bottomless Brunch at Casa

Bottomless Brunch at Casa Hotel

Get together with friends and loved ones to enjoy a Bottomless Brunch at Casa Hotel. 

Read more >
Chesterfield Canal Paddlespots
–

Paddlesports on Chesterfield Canal

Try something different this summer and have a go at Paddlesports along the Chesterfield Canal. Paddlesports are available to hire from Hollingwood Hub.

Read more >