As October settles over Dorset, the county shifts gear: summer crowds fade, misty mornings drift over heathland, and the landscapes glow with amber and gold. Whether you’re staying in one of our holiday cottages for October Half Term or just planning a day trip, here’s your go-to guide to what’s on in Dorset in October, half term fun, seasonal walks, spooky thrills — and cosy indoor escapes.
Autumn in Dorset is packed with family fun, spooky trails, music festivals, fireworks, and more! Whether you’re chasing Halloween thrills, enjoying local food and drink, or taking in the changing colours of the countryside, there’s plenty to see and do this October – and here our some of the things we are looking forward to the most.
Dates: 25th October – 2nd November 2025
Bring your teddy bear (or borrow one) and send them whizzing down the famous teddy zip wire this October Half Term. Families can also take part in a fun-filled quest to find the critters that call Corfe Castle home.
Find out more
Dates: 28th September – 4th October 2025
A week of fun culminating in the spectacular carnival procession on 4th October. Expect floats, music, and plenty of community spirit.
Find out more
Dates: 3rd – 5th October 2025
Enjoy a weekend of open mics, jam sessions and headline blues performances across multiple venues in Swanage.
Find out more
Dates: 3rd – 4th October 2025
Held in the Ocean Room at Weymouth Pavilion on 3rd to 4th October, this seaside beer festival features over sixty real ales and ciders from Dorset and beyond.
Find Out More
Dates: 3rd – 5th October 2025
Ahoy, matey! Dive into a weekend of pirate antics with live music, cannon fire, and re-enactments. Great family fun in Weymouth – especially if you’re stying in a Weymouth holiday cottage nearby.
Find Out more
Dates: 18th October – 2nd November 2025
Follow a spooky trail through the gardens, complete quizzes, and discover ghostly surprises along the way.
Find out more
Dates: 17th – 31st October 2025
Explore the Himalayan Garden filled with pumpkin creatures, spiders, and bats. Treats and home-grown pumpkins await at the end!
Find Out More
Dates: 25th October – 2nd November 2025
Hunt for pumpkins hidden around the castle grounds and solve clues for a prize. Fancy dress welcome!
Find Out More
Dates: 23rd October – 2nd November 2025
A dazzling illuminated Halloween trail with ghostly walks, scarecrows, and delicious food and drink. Perfect for families (and dogs!).
Find out more
Dates: 25th October – 2nd November 2025
Six spooky games designed for under-10s, including skeleton hunts, spider challenges, and gooey fun. Kids just £1 with a paying adult.
Dates: 25th – 31st October 2025
Enjoy spooky fun for little ones, with daily Halloween activities at this popular family farm park.
Find out more
Date: 31st October 2025
Children in full Halloween costume get free entry! Enjoy themed fun and spooky surprises at this famous rescue centre.
Find out more
Swanage 
4.9/5
Swanage
4.7/5
Nr Dorchester
5/5
Dorchester
0/5
Gaunts Common
4.8/5
Portesham, Nr Abbotsbury
4.8/5
Dorchester
5/5
Corfe Castle
4.9/5
Swanage
5/5
Swanage
4.7/5
Weymouth
4.8/5
Weymouth
5/5
Swanage
5/5
Sutton Poyntz, Nr Weymouth
5/5
Swanage
4.8/5
Langton Matravers
4.8/5
Dorchester
0/5
Swanage
4.6/5
Dorchester
5/5
Swanage
4.9/5
01929 481547