If you’re thinking about a summer break in Sherborne or the wider Dorset countryside, you’ve picked a brilliant time to visit. The town really comes alive over the warmer months, with everything from music festivals and historic pageants to food events and local markets.

We’ve pulled together some of our favourite Sherborne summer events and Dorset festivals happening this year—perfect if you’re planning a stay at The Hillbrook or looking for an excuse to book one.

Sherborne Market

Various dates throughout the summer

If you want to get a feel for Sherborne, the market is a great place to start.

Held on various dates throughout the summer, it’s full of local produce, handmade goods, antiques and the kind of finds you didn’t know you needed.

It’s relaxed, friendly, and very easy to lose an hour or two just wandering.

Staying at The Hillbrook means you can dip into town for the market in the morning, then head back and take things slow for the rest of the day.

Sherborne Abbey Festival

30 April – 7 May 2026

There’s something pretty special about hearing live music inside Sherborne Abbey. The festival runs for a full week and brings a mix of classical, choral, jazz and more contemporary performances to the town.

You don’t have to be a music expert to enjoy it either—just being in that space, especially in the evening, is worth it.

It’s a lovely way to ease into the summer season, and if you’re staying at The Hillbrook, you’re only a short trip away from the abbey doors.

Sherborne Castle Country Fair

25 May 2026

This is one of those classic Dorset days out.

Set in the grounds of Sherborne Castle, the Country Fair is packed with things to see—falconry, vintage tractors, dog shows, local food, and plenty for families too.

It’s a really easygoing countryside day out—traditional, friendly and authentic.

You can easily spend the whole day there, then come back to The Hillbrook for a quieter evening and a bit of a reset after all the activity.

Sherborne Pride

28 June 2026

Sherborne Pride is one of the most upbeat days of the summer.

It starts with a parade through town and rolls straight into a Party in the Park with live music, performances, and a welcoming atmosphere.

Whether you’re going with friends, family, or just turning up to see what it’s all about, it’s easy to get caught up in the energy of it.

If you’re staying at The Hillbrook, you’re close enough to enjoy it all without worrying about getting home.

Sherborne Castle Classic & Supercars

26 July 2026

Set in the grounds of Sherborne Castle, this is a great summer event whether you’re into cars or just looking for a good day out.

The setting alone makes it worth the visit, but the mix of classic cars and modern supercars keeps things interesting.

This year, there’s even more reason to go, with TV presenter Richard Hammond confirmed to attend — always a crowd favourite and a great addition to the day. It’s relaxed, not too crowded, and easy to wander at your own pace. A good option for a laid-back summer day, especially if you’re staying nearby at The Hillbrook.

Great Dorset Chilli Festival

1 – 2 August 2026

This one’s a bit different — in a good way. The Great Dorset Chilli Festival is lively, slightly chaotic, and a lot of fun.

There’s loads of food to try (some of it seriously spicy), cooking demos, music, and a few quirky competitions thrown in.

You don’t need to love chilli to enjoy it, but it definitely helps.

After a day here, heading back to The Hillbrook for something a bit calmer feels like the perfect balance.

Make a Stay of It

With so many events in Sherborne this summer and across Dorset, it’s worth turning your visit into more than just a day trip.

At The Hillbrook, you’ve got a quiet, comfortable base just minutes from the town — close enough to dip into the events, but tucked away enough to properly switch off afterwards.

Whether you’re here for a festival weekend or a slower countryside break, it’s an easy place to settle into.