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Historic Main Street


Main Street located in Road Town on the beautiful island of Tortola, the largest island in the British Virgin Islands archipelago, can easily be underappreciated by both visitors and citizens unless we pause and consider its underappreciated beauty and its role as the nucleus of business in the territory. Main Street has birthed many businesses over the years and remains a key area in Tortola’s economy.

In the 60s, the BVI experienced a transition from a place deemed as a bird sanctuary to a thriving economic centre. BVIslanders began to draw on their ingenuity to create services and make space for innovations that would drastically improve the lives of its people. So, if you want to understand how Main Street became a major player in this economic renaissance, press your clothes, put on your working shoes and walk with me down memory lane.

Step right into BVI history as you take the trek along the one-way street from the Junction of the Governor’s Office up to where the cemetery meets the entrance of Joes Hill.

Governor’s House

What is most enthralling about most of the buildings is that they have sheltered many families who grew up in the midst of Main Street, became businessmen/women developing Main Street and expanded their horizons into various sections of the British Virgin Islands. Tailors, Carpenters, General Store, Rum Shop and Night Club Owners, Butchers, Bakers, Teachers, Lawyers and Doctors to name a few. In those days, the Proprietor and his/her family would live upstairs and the shop would be housed downstairs. These included families bearing the surnames Smith, Scatliffe, Nibbs, Bacon, Peebles, McKetney, Donovan, Pickering, Shirley, De Castro, Hanley, Norman, Georges, Scott, Dawson, Simmonds, Winter, Peets, Benjamin, Wheatley, Rhymer, Creque, Penn, Abbott and Titley. These persons and their offspring are people we know and love living in the Virgin Islands and they have contributed massively to the territory for generations and continue to do so in key industries.

Peebles Hospital

Peebles Hospital: As you venture past the hospital – the territory’s medical history jumps out at you. It was first called Cottage Hospital and over time it became Peebles Hospital. Major Herbert Walter Peebles was responsible for constructing the Cottage Hospital amongst the ruins of William Rogers Isaacs’ former great house adjacent to Cameron Lodge [now Government House] in 1922. In the 1950s, the hospital was renamed after Major Peebles. During the early 90s, the name was briefly changed to the H.R. Penn Hospital, paying homage to Howard Reynold Penn OBE, a member of the Territory’s First Legislative Council. The name was quickly reverted back to Peebles Hospital. In 2014, a new hospital was built and in 2019 it was named in honour of Dr Daniel Orlando Smith OBE, BVI Chief Minister from 2003-2007 and Premier from 2011-2019.

Adina Donovan’s Home

Adina Donovan’s Home: On the other side of the street resides Adina Donovan’s Home which was the nursing quarters for the then Peebles Hospital. It is now the primary government-owned residential care facility for the indigent and elderly in the Virgin Islands. After two minutes of walking, you will meet the old Tortola Times building. Quite worn-down by the 2017 hurricanes but let’s acknowledge its legacy. This side on Main Street is considered to be the back of the building and the front is now on Water Front Drive currently owned by the Richardsons which operates Richardson Rigging.

The name Norman Fowler (American) is remembered for setting up THE TORTOLA TIMES here in the rear of this building. In the front part of the same building were the offices and vault of his bank, The Tortola Trust Company and Upstairs The Tortola Theatre, a hundred-seat cinema having four performances a week of cowboy pictures. http://www.hillmanweb.com/everitt/builders/fowler.html

History in the making. Interestingly FedEx, Dr Tattersall, Jack Smith-Hughes, Bank of Nova Scotia, and Mr Barker’s Office all had their beginnings in this very building. The other current buildings on this street is still owned by most of the families, but have been refurbished.

The Old Post Office

The Old Post Office: Within five minutes you should meet the old Administration Building, fondly called the Old Post Office. This majestic building – even in its state of disrepair – was born in 1866. It had heavy foot traffic until 2001 when the upper storey was destroyed by fire. Any person old enough to remember the old stencil machines used to prepare government circulars, typewriters and the printing press would also remember how proud Civil Servants were to be part of the Virgin Islands Public Service. The building not only housed the Post Office, but several other offices resided at the Administration Building including the Legislative Council from 1867 to 1902. Certainly, with some renovations, this building could be made into a Virgin Islands Museum. Pause and take a few pictures to have of this treasure.

J. R. O’Neal Building

J. R. O’Neal Building: To the left is a building owned by Mr. J. R. O’Neal, a noted BVIslander, entrepreneur and environmentalist. The J. R. O’Neal Building now houses several offices including the Complaints Commissioner’s Office. However, it also housed the J.R. O’Neal Pharmacy which sold pharmaceutical and beauty products. It also included a dental service space and a photo shop. Adjacent was a larger-scale general merchandising enterprise, the J.R. O’Neal Hardware Store. The building is currently being leased as a commercial space. https://jomaproperties.com/organization/

Sir Olva Georges Plaza

Sir Olva Georges Plaza: What many would consider the heart of Main Street would perhaps be the Sir Olva Georges Plaza. Besides the prestige the namesake brought to the Territory as the only BVIslander to be honoured with a knighthood; he was the recipient of the Territory’s first state funeral in 1976 and served in the Legislative Council. The area represented the economic hub of Main Street as it bordered the waterfront. Many people would also remember several Government offices being accommodated at the plaza along with the famous Esme Bookstore which provided a good read for those hungry for literature. Some even remembered when the horses and donkeys were tied between the Old Post Office and the Pharmacy to keep them safe as persons enjoyed the market day before returning to the country. The plaza has long been the meeting place for the farmer’s market and is still home for this activity in 2023. On early Saturday mornings, you can see vendors chatting merrily with each other and getting ready to show off their produce and other wares. On the opposite side, facing the Eastern Caribbean Court Building is where you can meet the fisherfolks from Anegada on Tuesday and Thursday mornings to purchase lobsters, conchs, and fish, once they are in season

These days, if you listen keenly you can hear the full-blown dialect of the BVI people. This would certainly take you back to yesteryears, watching men and women hustle across the street to load and unload laden sloops with all manner of goodies on the waterfront. Ever heard about the Home Industry? It’s a conversation to have with your grandparents. https://www.caribbeanislands.com/british-virgin-islands/

The H. R. Penn Building

The H. R. Penn Building: The H. R. Penn Building is located on the right. It has a new look and bears no. 90 Main Street. Mr Penn along with being a builder and general store owner has served his country as a member of the first Legislative Council. Visualize walking into a wooden treasure chest where every corner is bursting with an array of items required by every household.

BVI Architecture: The vibrant and beautiful BVI architecture is reflected all along Main Street. The brightly coloured exterior with the shuttered windows reflects the spirit of the people and is an ode to West Indian-styled architecture heavily influenced by European settlers.

BVI Folk Museum

BVI Folk Museum: A walk down memory lane is allowed as Irma and her sister Maria relocated this building and its contents. The foundation with the beautiful bricks still stands and if luck would have it, maybe one day, we may come upon the Arawak and Carib pottery and stools, some artefacts from the Wreck of the Rhone and other BVI treasures in some other part of the island of Tortola.

Island Sun Newspaper

To the very end of the street, not more than another two minutes walk on your left-hand side is the island’s oldest newspaper – The Island Sun Newspaper. The Island Sun Newspaper commenced operations on June 23rd, 1962, and was located 2 houses down from Midtown (close to Joyce Titley Craft Shop owned by Norwell Harrigan before it moved to its present location. It was managed by Carlos Downing and his wife Esme De Castro. Mr Downing served as Chief Editor but was not deterred by the closure of the Tortola Times founded by Fowler. With much community support and hardly any public or financial backing, they slowly made their mark. Of the many honours bestowed upon Carlos Downing, none ranked higher than the honorary BVI citizenship presented to him in 1983 by the then Chief Minister of the British Virgin Islands, H. Lavity Stoutt. The success of the newspaper saw the creation of Sun Enterprises (BVI) Ltd (a locally owned and managed company) which became the official publisher of the oldest-running newspaper of the BVI.

Carlos Downing continued as Editor for a short while and then Vernon W. Pickering became Chief Editor. Between 1986 and 1989, The Island Sun published a mid-week edition which came out on Wednesdays. The quaintness and size of the building cannot properly demonstrate the magnitude of work completed under its roof. It boasts that during the first 50 years of uninterrupted publishing, contributing writers and columnists included among others British aviation pioneer and hero Sir Alan Cobham, Dr Norwell Harrigan, Dr Pearl Varlack, Godfrey deCastro, Dr Pierre Encontre, McW. Todman, QC, Sir. Ronald Sanders, Dr Quincy Lettsome, Dr Giorgio Migliavacca and Clarence Christian.

Under Mr Pickering’s tutelage, the Island Sun fully developed into not only a dependable source of reference but has become a household name in the process too. Its publication each week is always eagerly awaited, and it developed a growing worldwide distribution network. In 1997 The Island Sun became the first Virgin Islands (US and British) newspaper to have its website. A recent survey of the daily traffic on The Island Sun website has shown an average of 3,500 visits per day, and on certain days as many as 18,000 accesses have been reported.

In 2002 the BVI Postal Authority issued two stamps to commemorate the 40th anniversary of The Island Sun depicting the front page of the 25th-anniversary edition and other front pages including the first one, the newspaper’s founders: Carlos Downing and Esme DeCastro-Downing were pictured on the other stamp. The colors on the building are as vibrant as the personalities that have kept this business alive here at No. 112. Be sure to get the number of the building in your next picture. https://www.islandsun.com/the-island-sun-story-1962-2019/


Old Customs House: Forming the corner of the street is an old relic, recently renovated due to Irma and Maria, but holding just as many memories, is the Old Customs House also known as the Point.

This Building currently houses Hucksters and Island Roots Coffee Shop, but many of the older folks will remember it as a warehouse for the storage of sugar. A different generation of folks will describe the boats that would dock right at the back of the building before the reclamations. If you slide your hands along the walls you can almost hear the Smith’s children’s laughter. Quite a lot of his history in those old walls as it was also home to a few shops.

Stay tune for a little more about the Social Inn, (the little guest house) that was housed in the area of Sunny Caribbee owned and operated by the Creque’s. Some recall the Judgement Day Hotel. The history of Main Street is as long as the road is long and will take some telling. Stay tune!