The best family-friendly hikes and walks around Dewlish
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2,243
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Family friendly hiking trails around Dewlish are set within the picturesque chalk hills of the Dorset Downs, offering a diverse landscape for outdoor exploration. The region is characterized by rolling countryside, a mix of open fields, varied woodlands, and gentle streams like the Devil's Brook. This topography features plentiful, yet not overly steep, hills, providing an engaging environment for hikers of all ages.
Best family friendly hiking trails around Dewlish
- The most popular family friendly hiking route is The Oak…
Last updated: May 4, 2026
5
hikers
2.62km
00:43
50m
50m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
5.0
(1)
2
hikers
12.0km
03:16
180m
180m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
5.0
(1)
2
hikers
14.6km
03:57
210m
210m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
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Tips from the Community
"Little England" in Milborne St Andrew refers to a specific historic, detached cottage that is officially designated as a Grade II Listed Building by Historic England. It is a picturesque structure believed to date back to the early 17th century, featuring traditional plastered cob walls, a half-hipped roof, and an attic with four half-dormers. Its historical importance is highlighted by remaining architectural details like a 17th-century oak mullioned window and an original roof structure. Today, the name "Little England" is also used to refer to both the historic house and the surrounding area, which contains other properties, including a holiday rental known as Little England Cottage and a bed and breakfast, making it a distinctive and tranquil residential location within the village.
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St Andrew's Church in Milborne St Andrew, Dorset, is a historic Anglican parish church with roots tracing back to the 12th century. It has 12th-century origins, featuring a tower and porch that date back to the 15th century. The church underwent extensive restoration and enlargement around 1876, overseen by the famous Victorian architect George Edmund Street. It is a Grade II* listed building, designated for its special architectural and historic interest. The structure is built of flint with stone dressings and tiled roofs. Notable internal features include a 12th-century tub-shaped font with cable moulding, a 15th-century waggon roof in the nave, and a re-set 12th-century chancel arch with chevron ornament now located at the vestry entrance. It also contains an early 16th-century monument to John Morton, a former Cardinal and Chancellor to Henry VII.
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In 1940 Dewlish was bombed by squadrons of German bombers and fighters. Just before D Day in 1944, the main American assault force onto Omaha Beach, trained and camped at Dewlish. They went straight from Dewlish to the ships at Weymouth.
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Good stop for refreshments. We were made very welcome and served good coffees. Web link for the Martyrs: https://martyrsinn.com/ Good info on the Tolpuddle Martyrs on the website. Free house and,I think, it is community owned.
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Take tour and taste 3 different types of wine for £15. You can also have lunch here or some cake
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The Martyrs is a Freehouse and has been saved from closure by the community. I was made welcome and enjoyed a homemade soup. The menu was not wide and not Gastro but in our experience rather good. Info on pub and the martyrs: http://martyrsinn.com/
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In 1940 Dewlish was bombed by squadrons of German bombers and fighters. Just before D Day in 1944, the main American assault force onto Omaha Beach, trained and camped at Dewlish. They went straight from Dewlish to the ships at Weymouth.
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Frequently Asked Questions
How many family-friendly hiking trails are available around Dewlish?
Dewlish and its surrounding area offer a wide variety of hiking opportunities. You'll find nearly 180 routes, with 86 classified as easy and 85 as moderate, making it simple to choose a path that suits your family's abilities.
What kind of landscape can we expect on family hikes near Dewlish?
The landscape around Dewlish is characterized by picturesque chalk downland, rolling countryside, and gentle valleys. You'll often walk through a mix of open fields, varied woodlands, and along gentle streams like the Devil's Brook, providing a serene and diverse backdrop for your family adventure.
Are there any easy, shorter loop walks suitable for families with young children?
Yes, there are several easy options. For a pleasant, shorter loop, consider The Oak at Dewlish – Dewlish War Memorial loop from Dewlish. This route is just over 2.6 km and offers a gentle introduction to the local scenery.
What are some interesting historical or natural landmarks we can see on family hikes?
Many trails pass by significant points of interest. You could explore the area around the historic Tolpuddle Martyrs' Tree, a site rich in local history. Other notable attractions in the wider region include the impressive Cerne Abbas Giant and the ancient Maumbury Rings.
Are the family-friendly trails around Dewlish suitable for dogs?
Many trails in the Dewlish area are dog-friendly, offering open fields and woodland paths for your canine companions to enjoy. However, always keep dogs under control, especially when passing through livestock fields, and check local signage for any specific restrictions.
What is the average duration for a family-friendly hike in this area?
The duration varies depending on the route's length and your family's pace. Easy trails, like the 2.6 km Dewlish War Memorial loop, can take around 45 minutes to an hour. Longer moderate routes, such as the 12 km Tolpuddle Martyrs' Tree – St Andrew's Church loop, might take 3-4 hours, perfect for a half-day adventure.
Where can we find parking for family walks near Dewlish?
Parking is generally available in or near Dewlish village, often close to trailheads or local amenities. Specific parking details can usually be found on individual route descriptions on komoot, helping you plan your starting point.
What do other hikers say about the family-friendly trails in Dewlish?
The komoot community highly rates the trails around Dewlish, with an average score of 4.6 stars from over 420 ratings. Reviewers often praise the peaceful countryside, the well-maintained paths, and the varied scenery that makes for an enjoyable family outing.
Are there any nearby villages or attractions worth visiting after a hike?
Absolutely! The nearby Milton Abbas Village is renowned for its picturesque thatched cob houses and is considered one of Dorset's most attractive villages. For a historical garden experience, Athelhampton Gardens is also a short drive away and offers beautiful grounds to explore.
What is the best time of year to go hiking with family in Dewlish?
Spring and summer are particularly lovely for family hikes in Dewlish, when the chalk downlands are vibrant and the woodlands are lush. The gentle hills and well-drained paths also make autumn and even mild winter days enjoyable, offering different seasonal beauty.
Are there any longer, moderate family hikes that offer more of a challenge?
For families looking for a longer adventure, the Dewlish War Memorial – Tolpuddle Martyrs' Tree loop from Dewlish is a moderate 14.5 km route. It offers extensive downland views and explores more of the historical landscape, providing a rewarding experience for active families.
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