4.7
(25)
86
riders
27
rides
Mountain biking around Chilmark offers a diverse landscape of preserved farmland and rolling hills. The region features extensive trail networks, including wooded paths and coastal access points. Significant features like Menemsha Hills Reservation and Peaked Hill provide varied terrain and elevated viewpoints. This area presents a mix of challenging climbs and enjoyable descents for mountain bikers.
Last updated: June 26, 2026
5.0
(2)
4
riders
44.6km
03:27
530m
530m
Moderate mountain bike ride. Good fitness required. Suitable for all skill levels.
5.0
(3)
4
riders
43.1km
03:49
760m
760m
Moderate mountain bike ride. Good fitness required. Suitable for all skill levels.

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3
riders
21.7km
01:53
330m
320m
Moderate mountain bike ride. Good fitness required. Suitable for all skill levels.
3
riders
43.2km
03:22
490m
490m
Moderate mountain bike ride. Good fitness required. Suitable for all skill levels.
4.0
(2)
3
riders
24.1km
01:56
380m
380m
Moderate mountain bike ride. Good fitness required. Advanced riding skills necessary.
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Probably the most doable sharp ascent on the Old Chalk Way. Long stretch of byway which trends downhill all the way to Salisbury. Line choice critical though, the speed bumps will definitely slow you down.
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Good climb, was across fields but fine today as they’ve been harvested. Might have been tricky earlier in the year
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Shear Water is an artificial lake created as part of the Longleat Estate. It's filled by a tributary of the River Wylye. It's a popular fishing destination.
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Amazing views of the hills. If your lucky you can see the gliders circling above from the Wing Farm Airfield
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Worth it for the road through Great Ridge but ultimately this isn't great riding. No alternative though so enjoy the mouthful of flies.
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Great Wishford sits in a meander of the River Wylye, beneath the chalk ridge adorned by the beautiful Grovely Wood. From the village, Grovely Road leads up to the woodland trails and is a good option for those looking to tackle some hill reps. According to an ancient custom, the residents of the village are permitted to gather firewood annually from Grovely Wood on Oak Apple Day, which is the 29th of May. The village pub, the Royal Oak, is a good shout for post run refreshment.
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Grovely Wood is one of Wiltshire's largest mixed woodlands and there's loads of trail running potential here. Particularly beautiful in spring, the chalk ridge it woodland adorns is a delight all year round. This section is part of the Monarch's Way, a 625-mile (1,006 km) long-distance trail that represents the escape route taken by King Charles II after his defeat at the battle of Worcester.
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First Broad Drive is an arrow-straight avenue through the heart of Grovely Woods. It's easy to pick up speed along this section; usually straight lines are something of a rarity where trail running is concerned. Unsurprisingly, given its trajectory, it was once part of a Roman road, a section of a trade route that connected the Mendips to the English Channel.
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Chilmark offers a diverse network of over 25 mountain bike trails. These routes traverse preserved farmland, rolling hills, and wooded paths, providing a variety of experiences for riders.
Yes, Chilmark features several family-friendly singletrack trails. While the provided routes are generally moderate, the region's diverse terrain includes options suitable for various skill levels, ensuring a pleasant experience for less experienced riders.
You can expect a varied landscape, from rolling hills and preserved farmland to wooded paths and coastal access points. Trails often include both challenging climbs and enjoyable descents, with features like those found in Menemsha Hills Reservation and Peaked Hill offering elevated viewpoints and diverse mini-environments.
Many of the mountain bike routes in Chilmark are designed as loops, offering a comprehensive riding experience without retracing your path. An example is the Maisie's Den – Ox Drove Concrete Path loop from Tisbury, which covers 28.8 miles through varied terrain.
While many routes are moderate, the region is known for its challenging climbs and varied terrain. For instance, the Cold Kitchen Hill Trig Point – Shearwater Lake loop from Fonthill Gifford is a moderate route featuring significant elevation gain and diverse landscapes, including views from Cold Kitchen Hill. The region also has trails like the Tiasquam Trail, known for its black diamond difficulty, and Old Farm Trail, which has an average grade of 11.2%.
Chilmark's tranquil setting and diverse landscape make it enjoyable for mountain biking throughout much of the year. Spring and fall offer pleasant temperatures and vibrant scenery, while summer provides warmer weather for combining rides with coastal relaxation at accessible spots like Menemsha Town Beach.
While many outdoor areas in Chilmark are dog-friendly, it's always best to check specific trail regulations or reservation rules before heading out with your pet. Some protected areas may require dogs to be on a leash or have restricted access.
The mountain biking experience in Chilmark is highly rated by the komoot community, with an average score of 4.8 stars. Riders often praise the diverse terrain, from rolling hills and preserved farmland to wooded paths, and the secluded, immersive riding experience offered by the extensive trail networks.
Yes, Chilmark and its surroundings offer several interesting sights. You can explore historical sites like Old Wardour Castle or New Wardour Castle. Natural highlights include Knowle Hill and the scenic Grovely Wood Forest Trail, which are great for combining with a ride.
For a route that offers varied singletrack and diverse terrain, consider the Hindon Village – Pertwood Singletrack East loop from Fonthill Gifford. This 13.5-mile trail is a local favorite, providing an engaging ride through different landscapes.
Yes, several trails provide expansive views. The Ox Drove Gravel Road – Descent to Broad Chalke loop from Tisbury offers scenic vistas as it traverses the landscape. Additionally, areas like Menemsha Hills Reservation and Peaked Hill provide sweeping views of Vineyard Sound, the Elizabeth Islands, and the Atlantic.
The Chilmark area is home to several natural monuments and viewpoints. You might encounter spots like Knowle Hill or enjoy the View of Cranborne Chase & West Wiltshire Downs. These natural features add to the scenic beauty of the trails.


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