
May is a wonderful time to enjoy Dorset, with longer days, blooming countryside and the coast looking its best. Spring is well and truly underway, bringing a relaxed atmosphere, outdoor events, local festivals and plenty of opportunities to explore the county’s towns, gardens and walking routes. With bank holidays and popular events throughout the month, booking ahead is recommended if you’re planning a spring break in Dorset.

Dates: 9th – 10th May
Dorset Spring Show is a lively May countryside event celebrating spring with farm animals, pony racing, craft demonstrations, food, flowers and family fun.
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Dates: 23rd & 24th May
Swanage Pirate Festival is a free, family-friendly weekend of pirate parades, cannon and sword displays, living history, sea shanties and beach battles.
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Date: 2nd – 10th May
Dorchester Walking Festival offers a week of guided and self-guided walks exploring Dorchester’s landscapes, history and countryside for all ages and abilities.
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Dates: 11th & 18th May
Weymouth’s Sunset Fish and Chips Cruise is a relaxing 3-hour golden-hour sail with Bennett’s fish and chips and scenic Jurassic Coast views.
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Dates: 22nd – 24th May
Bournemouth 7s Festival is a huge three-day sport and music event with competitions, live DJs, entertainment arenas and festival fun over the May Bank Holiday.
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Dates: 23rd – 31st May
Corfe Castle’s May Half Term – Stories and Seedlings offers family planting fun and interactive medieval storytelling tours bringing castle life to life.
Find out moreDo you want to keep up-to-date with what’s on in May in Dorset this year and the next? Our email newsletter will keep you up-to-date with the ins and outs of our lovely coastal county, including upcoming events, our favourite attractions and landmarks, and our latest accommodation offers. Sign up today and be the first to hear about what’s happening in 2026/27!