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Dorset Holiday Cottages
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What's on in Dorset in October 2025

Which Trusted Trader
Your Guide to Autumn Magic, Half Term & Local Events

What’s On in Dorset in October

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.

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October Events & Activities

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.

Corfe Castle in October

Corfe Castle in October

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.

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Gillingham Carnival

Gillingham Carnival

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.

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Swanage Blues Festival

Swanage Blues Festival

Dates: 3rd – 5th October 2025

Enjoy a weekend of open mics, jam sessions and headline blues performances across multiple venues in Swanage.

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Weymouth Oktoberfestfest

Weymouth Oktoberfest

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.

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Pirate Festival

Weymouth Pirate Festival

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.

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Halloween

Halloween Trail at the Walled Garden in Moreton

Dates: 18th October – 2nd November 2025

Follow a spooky trail through the gardens, complete quizzes, and discover ghostly surprises along the way.

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Halloween Trails in October

Halloween Trails at Minterne Gardens

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!

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Sherborne Old Castle

Sherborne Castle & Gardens Children’s Pumpkin Trail

Dates: 25th October – 2nd November 2025

Hunt for pumpkins hidden around the castle grounds and solve clues for a prize. Fancy dress welcome!

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Halloween Trail

Halloween at Moors Valley

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!).

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Swannary

October Half Term at Abbotsbury Swannery

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.

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11

October Half Term at Farmer Palmers

Dates: 25th – 31st October 2025

Enjoy spooky fun for little ones, with daily Halloween activities at this popular family farm park.

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12

Halloween Fun at Monkey World

Date: 31st October 2025

Children in full Halloween costume get free entry! Enjoy themed fun and spooky surprises at this famous rescue centre.

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Find an October Half Term

Holiday Cottage in Dorset

1 Westport Cottage Ph3 Web
Westport Cottage
Wareham
4.9/5
5
3
2
0
23rd - 31st October  £995.40
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Malvern Apartment image
Malvern Apartment
Swanage
4.5/5
2
1
1
0
24th - 31st October  £501.50
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Sweet Pea Cottage
Dorchester
5/5
4
2
1
1
28th - 30th October  £620.00
27th - 30th October  £668.75
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Lilac Cottage image
Lilac Cottage
Dorchester
5/5
12
4
3
1
24th - 29th October  £3,319.25
28th - 31st October  £2,963.75
+8 more stays
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Beach Approach image
Beach Approach
Swanage
4.8/5
4
2
1
0
24th - 31st October  £743.05
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Bronte Cottage image
Bronte Cottage
Wareham
4.8/5
4
3
2
1
23rd - 31st October  £956.55
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Owl Cottage image
Owl Cottage
Wareham
5/5
4
2
1
1
23rd - 31st October  £1,205.50
23rd - 30th October  £1,115.50
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Thistledown image
Thistledown
Dorchester
5/5
2
1
1
1
26th - 30th October  £653.75
23rd - 27th October  £695.00
+25 more stays
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Olive Cottage image
Olive Cottage
Swanage
5/5
4
2
1
0
23rd - 24th October  £362.86
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Rose Cottage image
Rose Cottage
Dorchester
5/5
3
2
1
1
24th - 28th October  £783.00
24th - 26th October  £689.50
+25 more stays
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Jasmine Cottage image
Jasmine Cottage
Dorchester
5/5
4
2
1
0
24th - 27th October  £818.75
26th - 31st October  £888.25
+25 more stays
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Seashell View image
Seashell View
Swanage
4.9/5
6
3
1
0
23rd - 31st October  £1,142.40
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Bluebell Cottage image
Bluebell Cottage
Dorchester
5/5
3
2
1
1
25th - 29th October  £672.50
24th - 28th October  £715.00
+25 more stays
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Compass Cottage image
Compass Cottage
Swanage
4.8/5
4
2
1
1
24th - 31st October  £967.50
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Poppy Cottage image
Poppy Cottage
Dorchester
5/5
4
2
1
1
24th - 29th October  £1,122.00
24th - 31st October  £1,320.00
+12 more stays
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holiday cottage in studland
Heathlands
Studland
4.6/5
6
3
1
0
24th - 31st October  £1,111.60
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Capstone image
Capstone
Swanage
4.9/5
8
4
2
0
23rd - 30th October  £1,275.40
23rd - 31st October  £1,379.55
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27 West Street Ph1 Edit Web
The Old Butcher’s Cottage
Corfe Castle
4.8/5
6
3
2
2
24th - 31st October  £1,278.55
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3 Puddledock Cottage image
3 Puddledock Cottage
Sutton Poyntz, Nr Weymouth
5/5
6
3
1
0
23rd - 27th October  £564.80
23rd - 29th October  £676.90
+12 more stays
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2018 Front PHOTO
Newton Manor Grange
Swanage
4.6/5
6
3
2
0
24th - 31st October  £936.25
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