There was early confusion as to whether Upwey should be spelled Upway, in the Liberty of Wayhouse, a contraction of Wayboyeux, the property having been originally owned by the Barons Bayeux
Set in a little wooded valley with the high bare downs above, the spring at Upwey known as The Wishing Well has been visited by tourists since they started coming to Weymouth in the later 18th century. It is the place where the river Wey rises and a sizeable stream emerges from the ground in two springs because the permeable Portland sand and stone meet the impermeable Kimmeridge Clay.
King George III was a visitor in the days when Sir Christopher Wren was the Member of Parliament for Upwey and Weymouth. He came to the well and drank from a Gold Cup, which later became the original Ascot Gold Cup.
One of the 'characters' of Weymouth between the two Great Wars was 'Surgeram' Shorey, a burly man with the red cheeked countenance of a Dickens villain, who sold logs from a horse and cart in winter, drove a horse bus for visitors in summer and swore heartily all the year round. His horse bus plied from the King's Statue, and for a few shillings conveyed the visitors to Upwey Wishing Well, with a cream tea thrown in. The Wishing Well was watched over by elderly ladies who in return for money, offered a glass of the water as it bubbled from the earth in the shadow of chestnut trees. Drink and your wish will come true they predicted
The little school by The Wishing Well was built in 1840 and a matching school-house is a little further along the road to the church. Opposite the well is a small early 19th century stone granary and a late 17th century cottage with characteristic mouldings round the windows.
Upwey Mill is a large Portland stone building dating from 1802. Thomas Hardy knew the family who lived here, and it is probably the mill described in 'The Trumpet Major', where Bob Loveday escapes the press gang by going up through the mill on the sack hoist. In front of it, on the road is the early 19th century mill house.
The church of St. Lawrence is pretty. the north aisle, the windows on that side and the porch are late 15th century, and were neatly matched on the other side when the south aisle was built on 1838. It has a heavy, but attractive 1841 roof. Nice woodwork, with a medieval porch door, 17th century pulpit and panelling at the east end of the north aisle. The three wooden panels with carved figures hanging on the walls are figures of saints, probably 17th century and from another pulpit. There is a 15th century font and several good 18th and 19th century monuments.
The most successful maritime commander in the history of the Customs and Excise service lies in peaceful obscurity in the church of St Lawrence at Upwey. The church contains a wall plaque to "Anna Floyer, Daughter of Warren Lisle Esq" but there is no memorial to the man himself [1699-1788]. His wife, Ruth, was also buried there, in 1790, and likewise lacks a stone.
The documentary record has been put right by the work of Graham Smith in his book Something to Declare. In Lisle's case they tended not to but he was to be responsible for seizures that totaled over £250,000, which in the currency values of the 1990s is upward of £25 million..