Dorchester Walking Festival 2026

Your Guide to a Week of Exploration

May is National Walking Month, and Dorchester is marking the occasion in style. The Dorchester Walking Festival is back for 2026, bringing together a fantastic programme of guided walks that celebrate the town’s rich history, stunning natural landscapes, and hidden corners that even many locals have yet to discover.

Running from Saturday 2nd May to Saturday 10th May, this is a brilliant opportunity to get active, connect with the community, and see Dorchester and the surrounding area through fresh eyes.

What is the Dorchester Walking Festival?

The Walking Festival is an annual community event that uses National Walking Month as a springboard to get people exploring on foot. Each walk is led by knowledgeable local guides, with routes ranging from scenic countryside trails to fascinating historical tours through the town centre itself.

It’s an event that genuinely has something for everyone. Families, history enthusiasts, nature lovers, and those simply looking to stretch their legs and enjoy the spring air will all find something to suit them across the week-long programme.

Importantly, the festival also gives back. Walk leaders choose local charities to receive proceeds from each event, and the results speak for themselves. In previous years, the Walking Festival has supported no fewer than 15 local charities.

What’s on at The Dorchester Walking Festival?

The programme this year is packed with variety. Here’s a flavour of what to expect across the week.

For those who love a scenic route, Walk by Train: Maiden Newton to Dorchester and Moreton to Maumbury Rings offer a wonderful way to arrive on foot and take in the Dorset countryside along the way. Walk on the Wildside and the Chesil and Portland Marine Walk are equally spectacular for those who enjoy the great outdoors.

History lovers are particularly well catered for. A Walk Through 17th Century Dorchester, In the Footsteps of Thomas Hardy’s Childhood, and The Hanging Judge: Baron Jeffreys each bring a different chapter of Dorchester’s past to life in an engaging and accessible way. Law and Literature in Dorchester and The Moule Family of Fordington are further highlights for those who enjoy learning as they walk.

For something a little more unexpected, A Folk Song Walk through Dorchester and Stories of Our Non-Native Trees in Borough Gardens offer a genuinely unique way to experience the town and its green spaces.

Here is the some of the other events taking place across the festival:

• The Hanging Judge – Baron Jeffreys, Sat, May 2 – 1:00pm
• Poundbury Walking Tour Sun, May 3 – 11:00am
• Walk on the Wildside Tue, May 5 – 9:30am
• Chesil and Portland Marine Walk Tue, May 5 – 10:00am
• Piddletrenthide/Lyscombe Nature Reserve Circular Tue, May 5 – 10:00am
• Walking in the paw prints of Wessex Tue, May 5 – 1:00pm
• A Folk Song Walk – Dorchester Tue, May 5 – 6:30pm
• In The Footsteps of Thomas Hardy’s Childhood Wed, May 6 – 10:30am
• Stories of our Non-Native Trees Wed, May 6 – 6:00pm
• Thomas Hardy’s Dorchester Thu, May 7 – 2:00pm
• Walk by Train – Moreton to Maumbury Rings Fri, May 8 – 9:30am
• Walk by train – Maiden Newton to Dorchester Fri, May 8 – 9:30am
• Swallet holes and Sand Lizards of Puddletown Forest Fri, May 8 – 10:00am
• Law and Literature in Dorchester Sat, May 9 – 11:00am
• The Big Brewery Square Dog Social Sat, May 9 – 11:00am
• A Farming Folk Song Walk – West Bexington Sat, May 9 – 2:00pm
• Sunday Morning circular from Sydling St Nicholas Sun, May 10 – 9:30am
• The Moule Family of Fordington Sun, May 10 – 11:00pm
• Dorchester Strollers Broadmayne Walk Sun, May 10 – 2:00pm
• Beating the Bounds Sun, May 10 – 3:00pm

Please note that some walks take place in the wider Dorset area surrounding Dorchester, so do check the individual listings for locations and meeting points. More guided walks are happening daily, so please check out the Walking Festival’s Eventbrite page for more information.

Make a Day of It in Dorchester

All those steps are bound to work up an appetite. Dorchester is home to a wonderful selection of independent cafés and restaurants, all of which make the perfect place to sit down, refuel and reflect on the walk you’ve just enjoyed. Take a look at our café and restaurant directory to plan your visit ahead of time.

Share Your Snaps

Taking part in the Walking Festival this year? We’d love to see your photos from across Dorchester and the surrounding countryside. Share your pictures with us by emailing info@dorchesterdorset.com and help us celebrate everything that makes this town and this festival so special.

FAQs – Dorchester Walking Festival 2026

What is the Dorchester Walking Festival?
The Dorchester Walking Festival 2026 is an annual community event celebrating walking, local history, and nature. It features a programme of guided walks led by knowledgeable local guides across Dorchester and the surrounding countryside.

When is the Dorchester Walking Festival 2026?
The festival runs from Saturday 2nd May to Sunday 10th May 2026, taking place during National Walking Month.

Where does the Dorchester Walking Festival take place?
Events are held across Dorchester and the wider Dorset area, including countryside locations, coastal routes, and historic town centre walks.

What types of walks are included in the festival?
The festival includes a wide range of guided walks such as:

• Scenic countryside and coastal walks
• Historical and heritage tours
• Nature and wildlife walks
• Themed experiences like music, literature, and local stories
• There is something suitable for all interests and fitness levels.

Are the walks suitable for beginners and families?
Yes, many walks are family-friendly and suitable for beginners, with a variety of distances and difficulty levels available throughout the programme.

Do I need to book the walks in advance?
Yes, most walks require advance booking, and spaces can be limited. Visitors are encouraged to check listings and book via the festival’s Eventbrite page.

Are the walks free to attend?
Some walks may be free, while others have a small fee or donation, often supporting local charities chosen by the walk leaders.

Does the festival support local charities?
Yes, the festival supports local causes, with proceeds from walks going to charities. In previous years, over 15 local charities have benefited.

What are some highlights of the 2026 Walking Festival?
Highlights include:

• “In the Footsteps of Thomas Hardy’s Childhood”
• “The Hanging Judge: Baron Jeffreys”
• Coastal routes like the Chesil and Portland Marine Walk
• Unique experiences such as Folk Song Walks and nature trails

Are there walks outside of Dorchester town centre?
Yes, many walks take place in the wider Dorset area, including countryside villages, coastal paths, and nature reserves. Always check meeting points when booking.

What should I bring to a walking festival event?
Participants should bring:

• Comfortable walking shoes
• Weather-appropriate clothing
• Water and snacks
• Any specific items recommended for individual walks

Is the Dorchester Walking Festival dog-friendly?
Many walks are dog-friendly, but this depends on the individual route and organiser. It’s best to check the specific event details before attending. There are also dog-focused events such as the “Big Brewery Square Dog Social” during the festival.

What else can I do in Dorchester during the festival?
Visitors can explore cafés, restaurants, and shops across Dorchester, making it easy to combine a walk with a full day out in the town.

Why should I visit the Dorchester Walking Festival?
The festival offers a unique way to explore Dorset on foot, discover hidden locations, learn local history, and connect with the community – all during the peak of spring.

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