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October 2026 Events & Days Out in Dorset and Hampshire

Discover what’s happening across Dorset and Hampshire this October, from live music and Oktoberfest celebrations to Halloween fun, pumpkin picking, autumn walks and family activities. We’ve rounded up some of the best events and seasonal days out for Shorefield Holidays ambassadors.

Shorefield Holidays

Dear Shorefield Holidays Ambassadors, here is your comprehensive guide to what’s happening around all of our Holiday Parks in October. 

Dorset & Hampshire October Highlights 2026 

As autumn arrives, October brings festivals, live music, beer events, Halloween fun, family activities and stunning seasonal days out across Dorset and Hampshire. 

Week 1: 1 to 4 October 

Swanage Blues Festival 
One of Dorset's most popular music weekends, featuring live blues performances across numerous pubs, clubs and venues throughout Swanage. [exploringd...rset.co.uk] 

Weymouth Pirate Fest 
Pirates take over Weymouth with live music, historical re-enactments, cannon fire, street entertainment and family-friendly activities. [exploringd...rset.co.uk] 

Shaftesbury Carnival (3 October) 
A traditional Dorset carnival with illuminated floats, entertainment and community celebrations. [exploringd...rset.co.uk] 

Week 2: 5 to 11 October 

Run Bournemouth (10 to 11 October) 
Choose from the Half Marathon, 10K, 5K or junior races while enjoying spectacular coastal views and a fantastic atmosphere. [dorsetlife...tyle.co.uk] 

Shaftesbury Oktoberfest (9 to 10 October) 
A Bavarian-inspired weekend featuring beer tents, live music, food stalls and traditional Oktoberfest fun. [exploringd...rset.co.uk] 

Bournemouth International Film Festival (9 to 10 October) 
Independent films, documentaries, workshops and industry networking events for film enthusiasts. [dorsetlife...tyle.co.uk] 

Week 3: 12 to 18 October 

Weymouth Oktoberfest (16 to 17 October) 
Enjoy more than 60 real ales and ciders, food vendors and live entertainment overlooking Weymouth Bay. [exploringd...rset.co.uk] 

Purbeck Film Festival Begins (16 October) 
Independent and international films shown at venues across Purbeck and Dorset. [dorsetlife...tyle.co.uk] 

Michael Spicer: Hope All's Well (17 October) 
The comedian and creator of "The Room Next Door" performs in Hampshire. [allevents.in] 

Week 4: 19 to 31 October 

Corfe Castle Half-Term Activities (24 October to 1 November) 
Family trails, castle activities and the popular teddy-bear zip wire return for October half-term. [exploringd...rset.co.uk] 

👻 Halloween Events Across Dorset 
Halloween trails, pumpkin-themed activities and spooky experiences take place throughout the county, including attractions such as Moreton Walled Garden. [exploringd...rset.co.uk], [dorsetlife...tyle.co.uk] 

 Pumpkin Picking in Hampshire Popular venues include: 

  • Sunnyfields Farm (Totton) 

  • Pickwell Farm (Southampton) 

  • Westlands Farm (Romsey) 

  • Finkley Down Farm (Andover) 
    Many offer pumpkin patches, maize mazes and Halloween activities. [familiesonline.co.uk] 

 Autumn Walks October is one of the best months to visit: 

  • New Forest National Park 

  • Mottisfont 

  • Hinton Ampner 

Top Picks Near Christchurch 

✅ Run Bournemouth (10 to 11 October) 
✅ Swanage Blues Festival (1 to 4 October) 
✅ Weymouth Pirate Fest (2 to 4 October) 
✅ Weymouth Oktoberfest (16 to 17 October) 
✅ New Forest Pumpkin & Halloween Events (throughout half-term) 
✅ Purbeck Film Festival (16 October onwards)

Useful Event Websites 

Please remember to check individual event websites before travelling, as dates, times and activities can sometimes change. 

October is a wonderful time to get out and about, enjoy the changing seasons and discover everything Dorset and Hampshire have to offer before winter arrives. 

We hope this guide gives you plenty of inspiration for your next day out! 

From your Shorefield Holidays Reception Teams 

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