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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.

https://www.iwm.org.uk/memorials/item/memorial/26665

Once you're at this well-known junction, also known as the Dorsetshire Gap, it doesn't matter which direction you head because the landscape in this area is breathtaking.

Bulbarrow Hill is situated within the Dorset Area of Outstanding Natural Beauty, which is known for its scenic landscapes and diverse ecosystems. The hill is part of the Dorset Downs, a range of chalk hills that extend across the county. It is one of the highest points in Dorset, with an elevation of around 274 meters (899 feet) above sea level. Due to its height, it provides panoramic views of the surrounding countryside, including the rolling hills, farmland, and picturesque villages that make up the Dorset landscape.

The Dorsetshire Gap is a very atmospheric location, very easy to imagine Medieval traders passing through it. Be aware that the bridleways too and from it are tough, the tracks marked on the maps may not exist on the ground, cycling can be hard an slow, Still worth a visit.

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.

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.

Dating from the late thirteenth century, St Martin's records the fortunes of Cheselbourne.  See the 14th century chancel, and in particular its south porch with 15th century sundial.

Grassy pitches. Beautiful sunsets as well if you’re lucky :)

Beautiful stretch but a donkey’s trail so not really for cycling. Bumpy stretches before and after, mtb/hikers terrain!

The Dorsetshire Gap is, or Dorset Gap as it's known for short, is a dip in the Dorset Downs chalk ridge between Nordon Hill and Nettleton Tout, close to the settlement of Higher Melcombe. A number of different bridleways run through and over this pass, including the ancient Wessex Ridgeway. It's thought that this point was part of a network of trading routes that date back as far as the Middle Ages.