As October rolls in, the Chiltern Hills come alive with crisp autumn air, golden woodlands, and a calendar full of family-friendly fun. This region, stretching across Buckinghamshire, Hertfordshire, and Oxfordshire, is perfect for parents seeking a relaxed countryside break mixed with exciting activities for kids. Whether you’re picking pumpkins in the fields, wandering through enchanted woodlands, or joining a heritage railway adventure, the Chilterns offer a magical balance of rural beauty and creative family entertainment.

For October half term, the Chilterns transform into a playground of discovery — from spooky trails and wildlife encounters to creative workshops and cozy village events. Here’s your guide to the top October half-term and Halloween activities for kids in the Chilterns in 2025.

1. Pumpkin Patch at Peterley Manor Farm, Great Missenden

When: 19 – 31 October 2025
Where: Peterley Manor Farm, Prestwood, Great Missenden

Kickstart half term with a visit to Peterley Manor Farm’s Pumpkin Patch, one of the most picturesque in the Chilterns. Families can wander the fields in search of the perfect pumpkin, explore the maize maze, and visit the on-site Little Orchard nursery for children’s crafts and face painting.

Why families will love it:

• A true countryside experience with hay bales, tractors, and farm-fresh produce.
• Instagram-worthy photo spots and wholesome outdoor fun.
• The café serves delicious seasonal treats like pumpkin soup and hot chocolate.

2. Bekonscot Model Village Spooky Trail

When: 25 October – 2 November 2025
Where: Warwick Road, Beaconsfield

The world’s oldest model village gets a seasonal twist during half term. Bekonscot Model Village invites children to join a spooky scavenger hunt, spotting hidden ghosts and ghouls among its miniature towns and railways.

Why families will love it:

• A gentle introduction to Halloween — fun, not frightening.
• The miniature details keep both kids and parents fascinated for hours.
• Free activity sheets and prizes for trail finishers.

3. Odds Farm Park Halloween Festival

When: 18 October – 2 November 2025
Where: Wooburn Common, near High Wycombe

Odds Farm is a staple for family days out, and their Halloween Festival is full of interactive fun. Kids can carve pumpkins, meet costumed characters, and enjoy animal encounters in the barns. There’s also a special “Pumpkin Magic Show” running twice daily.

Why families will love it:

• Combines animal fun, indoor play, and Halloween excitement.
• Great for younger children with themed crafts and mild scares.
• Cafés and picnic spaces make it ideal for a relaxed day out.

4. Chiltern Open Air Museum – Enchanted Museum Nights

When: 25 – 26 October 2025
Where: Chalfont St Giles

Step back in time for a twilight adventure at the Chiltern Open Air Museum. Families can explore candlelit cottages, meet historical storytellers, and enjoy spooky folklore tales under the autumn stars.

Why families will love it:

• A unique after-dark experience that blends history and fun.
• The storytelling is captivating but family-friendly — no nightmares here!
• Perfect for older kids and curious minds.

5. Roald Dahl Museum & Story Centre – Half-Term Story Workshops

When: 26 October – 2 November 2025
Where: Great Missenden

Celebrate one of the UK’s most beloved authors in his home village. During half term, the Roald Dahl Museum hosts themed storytelling sessions, creative writing workshops, and costume days where kids can dress as their favourite Dahl characters.

Why families will love it:

• Inspires reading and creativity through hands-on fun.
• Small-scale, welcoming venue perfect for families with younger children.
• Great cafés and bookshops nearby for a relaxed family day out.

6. Chinnor & Princes Risborough Railway – Wizard Express

When: 26 – 31 October 2025
Where: Chinnor Station, Oxfordshire

All aboard the Wizard Express! Families can climb aboard this historic steam train for a magical ride through the Chiltern countryside. Children receive wizard hats and activity packs, while onboard entertainers perform tricks and stories.

Why families will love it:

• Combines railway nostalgia with Halloween whimsy.
• Perfect for train-loving kids aged 4–10.
• Comfortable indoor setting with countryside views.

7. Wendover Woods – Forest Halloween Trail

When: 25 October – 3 November 2025
Where: Aston Clinton, Buckinghamshire

This Forestry England site offers a beautiful self-guided Halloween trail through the woods. Follow the map, complete nature-themed clues, and collect a spooky sticker at the finish.

Why families will love it:

• Outdoor adventure surrounded by stunning autumn foliage.
• Suitable for all ages — pram-friendly paths and easy navigation.
• Dogs welcome, making it a great option for pet-owning families.

8. Wycombe Swan Theatre – “Room on the Broom” Stage Show

When: 29 October – 2 November 2025
Where: Wycombe Swan Theatre, High Wycombe

Based on Julia Donaldson’s much-loved story, this musical adaptation of “Room on the Broom” brings magic, laughter, and song to the stage. With catchy tunes and colourful costumes, it’s a perfect treat for little theatre-goers.

Why families will love it:

• Short running time and engaging visuals ideal for kids aged 3+.
• Indoor entertainment for chilly autumn days.
• Nearby restaurants make it easy to turn into a family evening out.

9. The Hellfire Caves – Family-Friendly Halloween Experience

When: 25 October – 2 November 2025
Where: West Wycombe

A toned-down version of the famous spooky tours, the Hellfire Caves’ family-friendly Halloween experience introduces children to myths and legends in a safe, guided format. Costumes encouraged, and there’s a mini treasure hunt at the end.

Why families will love it:

• Exciting yet manageable level of spookiness.
• A chance to explore a real cave network steeped in local history.
• Guides are fantastic with kids, keeping the atmosphere fun and light.

10. Tring Natural History Museum – Creepy Creatures Week

When: 26 October – 2 November 2025
Where: Tring, Hertfordshire

Home to one of the UK’s best animal specimen collections, Tring Museum hosts “Creepy Creatures Week” — a mix of themed trails, quizzes, and real specimen encounters (think bats, spiders, and snakes).

Why families will love it:

• Educational and exciting — a great mix of nature and mystery.
• Free entry and family-friendly facilities.
• Staffed by knowledgeable volunteers who make learning fun.

Stay with Pass the Keys – Adam

For families exploring the Chilterns this October, Pass the Keys – Adam offers the perfect home base. His selection of fully managed holiday lets combines comfort and convenience with the charm of local living.

Stay in a cosy countryside cottage or a modern town apartment, all equipped with family-friendly amenities such as full kitchens, WiFi, and flexible check-in. Whether you’re out picking pumpkins or riding the Wizard Express, Pass the Keys ensures you return to a clean, welcoming space — the ideal ending to your family adventure in the Chilterns.