Top 10 festive activities to explore in Chesterfield this Christmas

Unwrap Christmas in Chesterfield this festive season and experience a host of exciting new events and attractions in the revitalised town centre. Discover unique gifts, experience playful events, savour festive flavours and enjoy Christmas fun, whilst creating memories together along the way.

Highlights this year include Santa’s brand-new cosy cabin Grotto in New Square, the Christmas pantomime at the newly refurbished 1435 theatre and museum and Chesterfield Christmas Market. Returning favourites include the Christmas Lights Switch On, Festival of Christmas Trees at the Church of St Mary and All Saints (the Crooked Spire), Tipi Christmas, Christmas-themed Puffin’ Billy rides at Queen’s Park, Steam Train Running Days at Barrow Hill Roundhouse and Santa Special Cruises on Chesterfield Canal to provide a festive adventure for all the family.

1. Christmas Lights Switch On – and a chance to meet The Grinch

See Chesterfield sparkle at the annual Christmas Lights Switch On, on Sunday 22nd November 2026. Enjoy festive fun in the town centre, from walkabout entertainment, fairground rides, performances from a brass band and you can even meet The Grinch at intervals throughout the afternoon, from 1pm! The main stage show will be hosted outside the Town Hall from 4.30pm – Becky Measures will host the stage show entertainment before the lights are switched on at 5.30pm. You will find live entertainment throughout the day in our town centre, featuring local musicians, choirs, dance groups, community performers and seasonal entertainers.

The Christmas Lights Switch on will be delivered by Chesterfield Borough Council thanks to support from by the Chesterfield Town Board Pride in Place programme, which is funded by the UK Government.

2. Chesterfield Christmas Market

Find Christmas shopping, food and entertainment all in one place at the Chesterfield Christmas Market from Friday 20th to Sunday 22nd November 2026. The Chesterfield Christmas Market will take place in our revitalised Market Place and New Square to get you into the Christmas spirit. Discover artisan gifts, handmade crafts, festive treats, seasonal food and drink, family-friendly attractions and live entertainment.

3. Santa’s Cabin in New Square

Visit Santa in his brand-new cosy cabin Grotto in New Square from Friday 27th November 2026 until Christmas Eve, where families can enjoy a magical Christmas experience. Santa’s new grotto is also dog friendly, meaning four-legged family members can join in the festive fun too. Well-behaved dogs are welcome to meet Santa and pose for photos alongside their owners. Quiet sessions suitable for those with special educational needs (SEN)will also take place on Sunday 29^th November 2026, Sunday 6^th and Sunday 13^th December 2026 between 10.00am and 10.30am. These sessions are highlighted in gold on the booking website. Bookings are now open and can be made by visiting: https://www.bookfatherchristmas.co.uk/ChesterfieldMarket

4. Christmas Pantomime

Make special memories this festive season at the Christmas pantomime in Chesterfield’s landmark theatre and museum, 1435.. Featuring the classic love story, Beauty and the Beast, this enchanting Christmas pantomime starts on Friday 4th December 2026 and runs until Sunday 3rd January 2027. Expect a magical journey packed with laughter, larger-than-life characters and plenty of panto mischief as Beauty and the Beast comes to life on stage. Television actor Jake Canuso from the hit series Benidorm takes the stage as Gaston, along with Award-nominated Dame Matthew Siveter, who leads the cast as the fabulously flamboyant Betty Bon Bon. With a brilliant cast, spectacular staging and just the right amount of silliness, this year’s show delivers festive fun for the whole family. Expect cheeky jokes, sing-along songs, and plenty of audience participation – oh yes there is!

5. Festival of Christmas Trees

Visit the Festival of Christmas Trees that is taking place at the Church of St Mary and All Saints (the Crooked Spire) from Saturday 14^th to Sunday 29^th November 2026. Admire a wonderful display of 120 Christmas trees at the iconic Crooked Spire Church that have been beautifully decorated by local charities, organisations and businesses. Now in its 13^th year, the festival continues to grow in popularity and has become a much-loved local tradition, bringing the community together to celebrate the festive season.

6. Tipi Christmas

Experience Tipi Christmas in the heart of town centre from Thursday 12^th to Thursday 31^st December 2026. The cosy Tipi will be located in New Square, and is the perfect place to meet friends and family and enjoy a delicious hot chocolate, mulled wine, or a seasonal treat. Open throughout the day and into the evening, Tipi Christmas is the ideal setting to relax and enjoy some festive cheer. With twinkling fairy lights and a roaring open fire, it’s a magical destination to get into the Christmas spirit.

7. Christmas-themed Puffin’ Billy rides

Enjoy a Christmas-themed Puffin’ Billy miniature train ride with all the family at Queen’s Park. Puffin’ Billy will be open for rides in Queen’s Park on 12^th, 13^th, 20^th and 21^st December 2026 from 10.30am to 4pm.

8. Santa Special Cruises organised by Chesterfield Canal Trust

Join Santa on Chesterfield Canal at Tapton Lock and Hollingwood Hub and have a special festive adventure on the Santa Special Cruises organised by Chesterfield Canal Trust. Enjoy a 30-minute short cruise and meet Santa on board, John Varley. Adults receive a mince pie and a festive drink, and children receive sweets and a gift from Santa. Cruises run Saturdays and Sundays from 28^th November through to 21^st December 2026, plus Tuesday 22^nd and Wednesday 23rd December 2026.

9. Steam Train Running Day at Barrow Hill Roundhouse

Visit the iconic Barrow Hill Roundhouse for one of their extra special Steam Train Running Days this festive season. Jump aboard the train hauled by a steam locomotive, take a trip up the Springwell branch line and see the Roundhouse site and the ever-changing line up in the yard from a different perspective. Explore the Roundhouse Museum and watch turntable and signal box demonstrations. Steam Training Running days are on 28^th and 29^th November 2026, and 5^th, 6^th, 12^th and 13^th December 2026.

10. Festive dining and drinks

Chesterfield is packed with ways to celebrate with the people who matter most this Christmas, from cosy pubs, welcoming cafés to delicious festive dining. Discover festive menus, Christmas favourites and seasonal drinks across our incredible range of independent restaurants, pubs and cafés. Fuel your shopping trip with a visit to Soresby Street Café for a festive cake or indulgent milkshake. Enjoy a Festive Bottomless Brunch at Barca Bar, Casa Hotel and tuck into a delicious selection of festive treats, from warm brie wedges with cranberry jam to fully loaded festive roasties. Treat yourself to fine dining at The Tickled Trout or the Red Lion Restaurant at Peak Edge Hotel.  Discover more food and drink experiences to try in Chesterfield at: https://www.chesterfield.co.uk/2026/05/50-food-and-drink-businesses-to-try-in-chesterfield/

The Christmas in Chesterfield website features a guide to all the events happening across the town, activities to take part in together, gift guides with unique offerings from local businesses, the ultimate list of food and drink venues to socialise at and a competition featuring a bundle of local experiences to win this Christmas.

Councillor Kate Sarvent, Chesterfield Borough Council’s cabinet member for town centres and visitor economy, said: “Christmas is such a special time for people to get together, and Chesterfield is certainly the place to get into the festive spirit. With a fantastic programme of events, entertainment and activities planned, there’s something for everyone to enjoy and we’re looking forward to seeing residents and visitors soaking up the magic of Christmas. The works we’ve been doing across the town centre have helped to create the perfect spaces to host a fantastic Christmas celebration for everyone to enjoy, with more space for entertainment and experiences for visitors.” 

Ann Fomukong-Boden, Destination Chesterfield Board Member, added: “Christmas is a wonderful opportunity to celebrate everything that makes Chesterfield special. From our independent businesses and creative communities to the fantastic range of events taking place, there’s so much happening across the town. What I particularly love is how these activities bring people together, creating opportunities to connect, support local businesses and make memories. It’s great to see Chesterfield continuing to develop as a vibrant, welcoming place for residents and visitors alike.”

The Christmas in Chesterfield campaign is delivered by Destination Chesterfield in partnership with Chesterfield Borough Council. To make the most of your Christmas in Chesterfield, visit: https://www.chesterfield.co.uk/christmas/