Are you wondering what’s on in Dorset in May? Aside from all the May half term activities happening across the county, there’s also plenty of other things to do. Dorset is home to some great theatres, family friendly attractions and festivals.
All of these happen throughout the year, so check out things to do in Dorset in May.
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Sherborne Abbey Festival
Dates: 30th April – 7th May 2026
Sherborne Abbey Festival is an annual, week-long celebration of music, with events held in a variety of locations in and around the beautiful town of Sherborne, Dorset.
Each year the Festival welcomes people from all over the UK to experience a wide range of performances and genres; from opera, choral and classical music to jazz, swing and more!
Teddy Rocks Festival
Dates: 1st – 3rd May 2026
Location: Charisworth Farm, Blandford, Dorset
One of the family friendly Dorset music festivals in Blandford. This is a three day festival raising money for the Teddy20 charity.
There’s plenty of activities and music through the weekend. Camping options are also available if you wish to stay on site for the weekend.
Shaftesbury Feastival
Dates: 2026 TBC
Enjoy the Bank Holiday weekend in Dorset at Shaftesbury Feastival. Stalls will be lined up along the length of town with lots of local food and drink.
There’s also be live cooking demonstrations outside Shaftesbury Town Hall. Don’t forget about the Cheese Races up Gold Hill!
West Bay Pirates Weekend
Date: 23rd -24th May 2026
There will be live music on the mound at West Bay from 3pm and an outside bar and BBQ. Enjoy the crafts stalls and games on the greens and finish off the Sunday with a firework display at 10pm.
Dorset Blind Association’s Motor Show At Lulworth Castle
Dates: 17th May 2026
Dorset Blind Association’s prestigious Motor Show returns to Lulworth Castle for its 10th year on the 17th May.
The show ground will offer a variety of artisan stalls selling local produce and handmade goods, food and drinks. There will also be live entertainment and a kids area with activities.
Swanage Railway Diesel Gala
Dates: 8th – 10th May 2026
The much loved long weekend of heritage diesel action returns to Swanage Railway. Services will service will operate on all three days over the full 10-mile line between Swanage and Wareham.
This and the beer festival at Corfe Castle station makes it a weekend not to be missed.
Discover more festivals in Dorset
North Dorset Cycle Ride
Date: 10th May 2026
Choose from the family fun ride to the 50 mile bike ride. The event is in aid of Prostate Cancer UK finishing on Gold Hill in Shaftesbury.
Hardy Half
Date: 10th May 2026
The Dorchester half marathon takes place across farmland and the iconic Hardy monument. The race will start and finish at Dorchester Rugby Club, and there will also be plenty of family friendly activities taking place.
Christchurch Cheese & Chilli Festival
Dates: 16th – 17th May 2026
Location: Parley Lane, Christchurch, BH23 6AD
The award winning Cheese and Chilli Festival is the only show in the UK which celebrates both Cheese and Chilli within a festival setting.
Expect a chilli eating competition, food challenges, cooking demonstrations, family friendly entertainment and plenty more.
Magic Of Thailand Festival
Date: 16th – 17th May 2026
Location: Baiter Park, Poole
You can expect to see live cooking demonstrations, authentic Thai cuisine food stalls, Thai boxing demonstrations, kids rides and plenty more. There’s also the I’m British Get Me Out of Here! eating competition.
Dorset Mud Run
Date: 16th – 17th May 2025
Dorset’s newest running challenge is 6km in distance and packed with mud, scenery and the best slide at the end.
After your run, there’s a bar and refreshments on offer to continue your day.
Cursus Cider & Music Festival
Dates: 22nd – 24th May 2026
This is a popular grassroots festival at Myncen Farm in Dorset. The 2026 lineup includes Peat & Diesel
There will also be a DJ tent, camp fire, kids DIY Den area, sports day and lots more.
Christchurch Food Festival
Dates: 23rd – 25th May 2026
Location: Christchurch Quay
Lots of different food and drink to tempt you. With pop up restaurants on the quay in the days leading up to the festival weekend. Why not enjoy one of the May Bank holiday festivals in Dorset with a visit to Christchurch.
Fayre In The Square
Dates: 23rd – 24th May 2026
Location: Hope Square, Weymouth
A weekend of live music and great food around Hope Square in Weymouth, working with Weymouth Rotary to raise money for local charities
Bournemouth 7’s Festival
Dates: 22nd – 25th May 2026
Location: Chapel Gate, East Parley, Christchurch, BH23 6BL
This is a popular festival in Dorset. It’s the World’s largest sport & music festival which attracts over 30,000 people to the coast every year.
Swanage Pirate Festival
Dates: 23rd – 24th May 2026
A full two days of piracy, living history, skirmishes and stalls.
Abbotsbury Swannery Food & Craft Fair
Dates: 23rd – 24th May 2026
Enjoy a weekend of fun at Abbotsbury Swannery this Summer. There will be plenty of food, drink and artisan craft stalls provided by Dorset Food & Drink. You can also enjoy the swan maze, pedal go karts, and arts and crafts.
Corfe Castle May Fair
Date: 25th May 2026
The Corfe Castle May Fair takes place on May Bank Holiday Monday in the castle grounds from 10:00 – 16:00. There will be plenty to enjoy including a fun dog show, raffle, refreshments, traditional fair games, plant stalls, book stalls, bric a brac and lots more.
Sherborne Castle Country Fair
Date: 25th May 2026
The Sherborne Castle Country Fair offer a wide programme of events, country activities, stands and entertainment. There’s also one of the largest Rare Breed Shows in the country.
For one day each year Sherborne Castle is transformed into a fun-packed Country Fair with attractions, entertainment and activities for all the family.
Wessex Folk Festival
Dates: 30th – 31st May 2026
Location: Weymouth Harbourside
The Wessex Folk festival, or otherwise known as the Weymouth Folk festival kicks off with a pre festival warm up night on the Friday
It’s one of the biggest, free festivals in England, drawing lots of crowds each year. You can expect to see around 30 live stage performances over the weekend, and plenty of stalls and entertainment.
Family Fest 2026
Dates: 29th – 31st May 2026
Location: The Meadows (Julians Field), Julians Road, Wimborne, Dorset, BH21 1EF
Set within the stunning Wimborne countryside across 12 acres of working farmland.
There will be live music across the two days, food and drink stalls, kids valley, funfair, amusements and a charity dog show. Weekend camping is also available.
Lulworth Castle May Half Term
Dates: 24th – 28th May 2026
Visit Lulworth Castle during May Half Term and enjoy animal and critter themed hunts and activities. The team from Mad 4 Animals will also be in attendance.
Race For Life Poole
Date: 30th May 2026
Choose from a 5k or a 10k distance raising money for Cancer Research. Your journey takes you through the stunning Poole Park and Baiter.
Pretty Muddy Poole
Date: 30th May 2026
If you fancy something different and don’t mind getting a bit muddy, then the Pretty Muddy in Poole is a great way to raise some money for charity.
You can scramble over the A-frame and crawl through the mud pit. The 5k distance disappears in a flash with all the fun obstacles you encounter on your route.
check out what’s happening in Dorset in June