Things to do in Chesterfield & Derbyshire this October half-term 2026

Pumpkin carving, spooky trails, steam train rides & plenty of free family fun. Here's what's happening across Chesterfield, Derbyshire and the Peak District this Halloween half-term.

October half-term is almost here. And if you're wondering how to keep the kids entertained for a whole week, there's plenty happening right on our doorstep.

From free Halloween activities in Chesterfield town centre to spooky adventures at Bolsover Castle, pumpkin carving in Matlock and autumn days out in the Peak District, we've rounded up some of our favourite ways to spend the school holidays.

Whether you're planning a full family day out or just looking for something to fill an afternoon, here are six places worth adding to your half-term plans.

1. Free Halloween fun at Chesterfield Market

Saturday 31 October | 10.30am–2.30pm | Free

Halloween doesn't have to cost a fortune.

Chesterfield Market is hosting a free Halloween Spooktacular, bringing face painting, crafts, entertainment and a pumpkin trail to the heart of the town centre.

Children can create their own Halloween masks, make spooky mini animations using handmade skeletons and pumpkins, and meet witch and vampire stilt walkers.

There's also a pumpkin trail around the market stalls and Market Hall. Find the hidden letters, solve the Halloween word and claim a sweet treat.

A brilliant option for families looking for free things to do in Chesterfield this half-term. And while you're in town, why not make a day of it and explore some of Chesterfield's independent shops and cafés?

Find out more: Chesterfield Halloween events

2. The Great Pumpkin Party at Bolsover Castle

24 October–1 November | 10am–4pm | Standard admission applies

A historic castle. Halloween costumes. And plenty of spooky surprises.

Bolsover Castle is hosting its Great Pumpkin Party throughout October half-term, with interactive storytelling, Halloween games and a themed trail around the grounds.

Little ones can get involved in the daily fancy dress competition, while the seasonal selfie spot provides the perfect opportunity for a family photo.

It's a chance to explore one of North Derbyshire's most impressive landmarks with a Halloween twist.

The activities are included with standard admission, with advance booking discounts available. English Heritage members can visit for free.

Find out more: English Heritage – Bolsover Castle

3. Pumpkin picking & spooky trails at Matlock Farm Park

24 October–1 November | Admission applies

If you're looking for a full day out, Matlock Farm Park has plenty planned.

Its Fang-tastic Halloween Festival returns with a spooky trail through the Forbidden Forest, complete with themed scenes, games and riddles.

There's pumpkin picking and carving, daily craft workshops with Witch Wendolyn and appearances from Halloween characters. Keep an eye out for the Headless Horseman, too.

On 24 October, visitors can also enjoy a special appearance from Elphaba and Glinda, with sing-alongs, games and photo opportunities.

And when you've had your fill of Halloween activities, there's still the farm park itself to explore, with animal encounters, sheep races, meerkat talks and indoor play areas.

A pumpkin is included for each child with a full paid entry ticket, subject to availability.

Find out more: Matlock Farm Park

4. Halloween adventures at Chatsworth Farmyard

24 October–1 November | Chatsworth, near Bakewell | Admission applies

Few places do an autumn day out quite like Chatsworth.

This half-term, the Farmyard and Adventure Playground are adding a Halloween twist to their usual activities, with creepy crafts, face painting and themed tractor and trailer tours.

Children can also get creative at the pumpkin carving station, available from 24–31 October.

Between the seasonal activities, little ones can meet the farmyard animals, enjoy animal feeding sessions and explore the adventure playground.

It's a lovely way to spend a few hours outdoors, surrounded by some of Derbyshire's most beautiful countryside.

Face painting and crafts are included with admission, while pumpkin carving and tractor tours carry a small additional charge. Book online in advance to receive free parking.

Find out more: Chatsworth Halloween Half-Term Fun

5. A Halloween trail in Stoney Middleton

3–31 October | Stoney Middleton, Peak District

For something a little more relaxed, swap the busy attractions for a wander around Stoney Middleton.

The Cupola is hosting a self-guided Halloween trail throughout October, inviting families to pick up a map and explore the village in search of seasonal surprises.

It's an excuse to get outdoors, enjoy some fresh Peak District air and discover one of the area's characterful villages.

Once you've completed the trail, head back to The Cupola for a look at its autumn and Halloween specials.

A good choice if you're after a slower-paced afternoon rather than a full day of organised activities.

Find out more: Check The Cupola's latest event information before travelling.

6. Halloween steam trains at Peak Rail

Saturday 31 October | Rowsley South, Derbyshire | Under-16s travel free

All aboard for a Halloween adventure.

Peak Rail is giving its heritage steam trains a spooky makeover for Halloween, with decorated carriages, fancy dress and free sweets for children.

The journey takes passengers through the beautiful Derwent Valley, combining a traditional steam railway experience with a little Halloween magic.

And there's a bonus for families: children under 16 travel completely free, with adult return tickets priced at £15.

Steam trains depart Rowsley South at 11am, 1pm and 3pm, with journeys travelling through Darley Dale towards Matlock.

There's no need to book ahead. Simply turn up and purchase your tickets on the day.

Find out more: Peak Rail Halloween Trains

More free things to do in Chesterfield this half-term

Looking for a few extra activities that won't stretch the half-term budget?

Chesterfield Borough Council is hosting two free outdoor activity days, perfect for children who enjoy getting creative and exploring nature.

Bug hotel workshop at Eastwood Park

Wednesday 28 October | 11am–2pm | Free

Head to Eastwood Park for a hands-on workshop where children can build their own bug hotel to take home or contribute to a larger bug hotel being created in the park.

There'll also be a Halloween-themed orienteering challenge and craft activities.

Just bring along a cardboard box or plastic milk bottle. All other materials are provided.

Find out more about Eastwood Park's free workshop

Bug hotel workshop at Holmebrook Valley Country Park

Thursday 29 October | 11am–2pm | Free

Another chance for little nature lovers to get involved.

Holmebrook Valley Country Park is hosting its own free bug hotel workshop, alongside Halloween-themed orienteering and crafts.

Children can take their creations home or contribute to a larger bug hotel being built in the park.

Again, you'll just need to bring a cardboard box or plastic milk bottle.

Find out more about Holmebrook Valley's free workshop

Half-term adventures, right on your doorstep

One of the things we love about Chesterfield and Derbyshire is just how much there is to explore nearby.

From independent shops and community events in Chesterfield town centre to historic castles, family attractions and the wide-open spaces of the Peak District, there's no shortage of ways to spend a weekend or school holiday.

And while Halloween might provide the excuse to get out and explore, these are the places that make living here special all year round.

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