4.5
(990)
5,805
hikers
18
hikes
Family friendly hiking trails around Crowborough are set within the High Weald Area of Outstanding Natural Beauty, offering diverse landscapes for outdoor exploration. The region features rolling hills, ancient woodlands, and expansive heathland, notably within Ashdown Forest. Geological formations like sandstone outcrops add unique character, while Crowborough Country Park provides tranquil walks through a disused quarry with streams and rock features. This varied terrain ensures a range of hiking experiences suitable for families.
Last updated: May 3, 2026
4.7
(6)
36
hikers
9.13km
02:28
120m
120m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
4.3
(4)
12
hikers
15.4km
04:21
320m
330m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

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4.0
(2)
12
hikers
8.00km
02:13
140m
140m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
6
hikers
16.9km
04:38
270m
270m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
5
hikers
14.3km
03:57
260m
260m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
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Beautiful escape from busy south east Easy walk. Muddy in winter.
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The Wealdway is an 82 mile (132km) long distance walking trail from Gravesend in Kent to Eastbourne in East Sussex. Here it walks along the edge of Five Hundred Acre wood, giving great views across the meadows and over the wider area of Ashdown Forest.
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This is Wrens Warren Valley, known as Eeyore's sad and gloomy place in the Winnie the Pooh book created by authors A.A. Milne, and E. H. Shepard. Yet more beautiful Winnie the Pooh trivia from Ashdown Forest.
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The Kings Arms is a Seventeenth century inn Formerly a barn in the seventeenth century it is said to be one of the most haunted pubs in Sussex
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Although the north chapel dates from the late 12th century, this church is primarily from the 13th century and was later remodeled in the 15th century with the addition of the tower and a porch.
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While several of its elements date back to the 14th century, such as the nave, the tower, or the north chapel, this church was rebuilt in the mid-17th century, with some additional elements added later, such as the south aisle.
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There are 17 family-friendly hiking trails around Crowborough, ranging from easy strolls to more moderate adventures. You'll find 5 easy routes perfect for younger children or those seeking a relaxed walk, and 12 moderate routes for families looking for a bit more challenge.
Crowborough, nestled within the High Weald Area of Outstanding Natural Beauty, offers a diverse landscape. You can expect rolling hills, ancient woodlands, and open heathland, particularly within the famous Ashdown Forest. Some trails might feature sandstone outcrops, adding a unique geological element to your walk. Paths vary from undulating circular tracks to more rugged woodland trails.
Yes, many of the family-friendly routes around Crowborough are circular, making them convenient for starting and ending at the same point. For example, the Kings Arms – St Denys' Church loop offers a moderate 9.1 km circular hike, and the Hiking loop from Crowborough is an 8 km circular option.
Crowborough's trails offer several interesting features. You can explore the ancient heathland of Ashdown Forest, famously known as the setting for Winnie the Pooh stories, where you might even find locations like Pooh Bridge. The region also boasts impressive sandstone outcrops, such as Harrison's Rocks, and the tranquil Crowborough Country Park with its ponds and a steep rocky gorge. For expansive views, consider routes that pass by viewpoints like Kidd's Hill.
Many of the trails in and around Crowborough are dog-friendly, allowing your furry family members to join the adventure. Ashdown Forest, for instance, is a popular spot for dog walking. However, always keep dogs under control, especially in areas with livestock or ground-nesting birds, and be mindful of local signage regarding leads.
The area is highly rated by the komoot community, with an average score of 4.5 stars from over 960 ratings. Reviewers often praise the diverse and picturesque landscapes, the peaceful escape offered by the Ashdown Forest, and the variety of trails suitable for different family abilities. The connection to Winnie the Pooh stories also adds a magical element for many visitors.
Absolutely! Crowborough borders Ashdown Forest, so many trails provide stunning vistas. The View of Ashdown Forest – Ashdown Forest loop is a prime example, offering extensive views across this iconic heathland. The Wealdway, a long-distance path, also skirts the edge of Five Hundred Acre Wood, providing excellent panoramas.
Crowborough is beautiful year-round, but spring and autumn are particularly lovely for family hikes. In spring, you can witness carpets of bluebells in areas like Crowborough Country Park. Autumn brings vibrant foliage to the woodlands. Summer offers longer daylight hours, while winter walks can be crisp and atmospheric, though some paths might be muddy.
Yes, for families seeking a longer outing, there are several moderate routes that offer a greater challenge. The Wrens Warren Valley – Five Hundred Acre Wood loop is a moderate 15.4 km trail, and the Millbrook Creek – View of Buckhurst Park loop covers 14.2 km, both providing ample opportunity for exploration and beautiful scenery.
Beyond the natural beauty, the region around Crowborough has historical charm. You might consider visiting Fletching Village and St. Andrew & St. Mary the Virgin Church, or the impressive Groombridge Place Manor House, which are accessible from some of the wider trail networks or as a short drive from Crowborough.


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