It’s an historic house just before the Somerset Bridge in Bermuda. It’s in a general state of disrepair these days, but once upon a time it was thriving and often served as the backdrop for photographs, paintings, and postcards. I’ve been doing a little research on the property, even pestering the Bermuda National Trust, and here are a couple of notes about the house.
(1) A quote from Molly Goes West: Discovering Bermuda with Paintbrush and Bike by Molly D Smith:
“Having completed my painting, I collected my belongings together and cycled back to Somerset Bridge where I ate my packed lunch on the shore line of the Somerset Bridge Post Office’s property. I wanted to paint Crossways, the old house by the bridge. so I obtained the permission of the post mistress to sit at the end of the post office veranda to do so. An elderly lady asked if she might watch me paint. I welcomed her company, so she drew up a chair borrowed from the post office.
I asked her what she knew about this lovely old property. She told me it was one of Bermuda’s most photographed 18th century cottages. It was badly damaged by fire in 1869 but was subsequently rebuilt much as it had been before the fire. My companion told me that, as was the case with many of the homes on the shore of Ely’s Harbour during Bermuda’s seafaring days, Crossways’ basement areas would have been used for cargo storage.”
(2) A quote from Bermuda’s Architectural Series: Sandys by the Bermuda National Trust:
Though never a Bridge House Tucker home, Crossways, one of the most photographed of Bermuda’s 18th century cottages and on the Merritt property from which the Bridge House property was sold, fits into the Somerset Bridge picture. Captain Elias Young acquired the property, through his 1755 marriage to Ruth Appleby, granddaughter of Nathaniel Merritt, with the small cruciform cottage that was already standing in 1735. A Major Tucker lived there in 1735, possibly John Tucker testing the waters for his permanent move to Sandys. Young left it to his wife Ruth who owned it when Henry Tucker’s Somerset Bridge Clab, a literary and scientific study group, used to meet there.
By 1824 it had passed to Mrs. Young’s daughter, Ruth Prudden, and in 1827 Mrs. Prudden advertised two houses at Somerset Bridge for rent, presumably Crossways and the neighbouring Garden House. In 1837 the property was advertised for sale in the Bermuda Royal Gazette and acquired by William R. Outerbridge, after whose death from consumption, it passed to his son, William R. Jr.
In 1869 the house was substantially damaged by fire, although the destruction cannot have been as great as the description in the newspaper would imply. The headline in The Royal Gazette reads, ‘Destruction of a dwelling house etc. by fire’ and goes on to report that the fine edifice…was reduced to ashes – a small portion of the roof and the darkened walls only remaining…’ This news report notwithstanding, the house was clearly rebuilt very much as it had been before the fire and was not replaced with a new house in the style of the time, thus leaving us with an important example of 18th century architecture and a popular subject for photographers.
The fire was associated with ‘a puncheon of strong rum’ which Outerbridge tried to roll out of the lower room and down the slope to the water. Unfortunately he struck the head of the puncheon on the doorpost, at which point the rum exploded. Outer-bridge, who was himself badly burned, also ran the Post Office from his business across the road. It is still the Post Office. His £10 supply of stamps was burned and in due course replaced, but by only £5 in stamps, an error not noticed until later and one that subsequently caused considerable tedious investigation by the Postmaster.
Thaddeus Hunt Dismont, by then the owner of Bridge House, acquired Crossways in 1888 and sold it to Clara Bolton in 1916. Canon Albert V. Sullivan purchased Crossways in 1937. After the death of his widow in 1967, the house was bought by the Galloway family.
(3) A quote from Bermuda Journey: A Leisurely Guidebook by William Zuill:
“During the eighteenth century a strong community life developed among the families at Somerset Bridge, and in 1765 these excellent folk formed a remarkable club which endured for upwards of seventy years. This was called the Somerset Bridge Club, and among its objectives was the acquisition of a library containing ‘all the books on economics in whatever language they have been written.’ Unemployment was seen to be a danger, and members pledged themselves to find work ‘suitable to their character for all lawful persons of both sexes,’ while a reward was to be offered to everyone who introduced into the colony ‘any new art or improvement to one already known.’ Finally, this extraordinary society dealt with old-age pensions—a question which we are apt to think has only been recognized in our modern, state-aided civilization; the club proposed to pension ‘all day labourers of unblemished reputation who after forty years of assiduous labour had not been able to amass a sufficient sum to make their latter days glide onward to their goal without inquietude.’
As we contemplate these lofty aspirations from the distance of our own disillusioned era, let us listen to an observer of a century ago who, likewise impressed with the Somerset Bridge Club, remarked that their purposes were ‘perhaps the most respectable monument which has ever honoured humanity.'”

(4) A quote from God’s Country by Elizabeth Jones
“Crossways, a picturesque cottage by Somerset Bridge, was for 70 years the meeting place of a literary and scientific association—thus proving life in Somerset during the eighteenth century wasn’t all about smuggling and adventures at sea. According to Jarvis, it was founded in 1765 near Bermuda’s first book and stationer’s shop owned by James Rivington of New York who opened it through a partner in Bermuda. A surviving printed pamphlet of rules bearing the signature of one Henry Tucker tells us, by 1784, the club was held “every Thursday night at the house of Mrs Ruth Young.” (Her husband, Captain Elias Young, had left her Crossways after he died.) The rules tell us that the annual dues would be 20 shillings a year until 1790 and members would be accepted by ballot. In addition to the annual fee, members also paid 1s 4d (one shilling and four pence) to the treasurer for books, pamphlets and magazines to pay for its extensive lending library.”