Masterworks exhibitions characteristically come with a catchy title. The name of their most recent, “Up Country, Down Country”, doesn’t disappoint. Its content is both fresh and original.

It explores an idea behind the well-known Bermudian expression that actually owes its derivation to the days of sail. The island’s prevailing westward winds blow from Somerset; hence you sail against the wind or “upwind”.

Conversely, sailing east to St George’s, you sail with the wind or “downwind” explaining the local monikers “Up Country” for Somerset and “Down Country” for St George’s.

In our early existence, sail was the pre-eminent mode of transport, facilitating trade and transportation. It’s demonstrated in this exhibit by two magnificent oil paintings, both by unknown artists.

Regatta, 1862 shows Bermuda-rigged boats in serene sail. The speedy sail revolutionised sailing and was invented here. Windward agility while tacking was a necessity due to the proximity of the hazardous reef.

The gallery space is dominated by a large, table-mounted map. The installation has numerous icons on top. It is brought to life as a replica train from the short-lived Bermuda Railway Company, and traces its way across the island’s nine parishes with accompanying sound effects.

Incidentally, the map is laid accurately west to east in the gallery and edged in red and blue; the colours of Somerset and St George’s cricket clubs.

The theme is continued with festive vintage Cup Match flags hung high above. Opposing walls depict paintings for Up Country and Down Country; divided with crisp blue wall text that aids the walk through.

The map is a clever device and integral to the interactivity of the show and its social context. It was designed as a work in progress and, as new ideas are formed, extra locations bound up with island history will be added including where famous artists, writers and celebrated visitors lived and worked.

Film is also celebrated. The 1925 footage of the American author Eugene O’Neill and John Held by the Hungarian photographer Nickolas Murray includes O’Neill’s Bermuda-born baby, Oona (future wife of Charlie Chaplin) plays in the gallery along with two silent films: the captivating 1925 movie Lovers In Quarantine starring Bebe Daniels, and the 1915 film Neptune’s Daughter, which was partly shot on Agar’s Island.

The refreshing feel to the show is enabled in part by new works from the permanent collection, many unseen before. Inland Shore(1939), the oil on canvas by American Clinton Brown, is a delight and conjures up a sense of calmness.

More than 35 pieces in acrylic by contemporary Bermudian artist Bruce Stuart comprise a show within the main exhibit.

The artist is recognisable for his naturalistic style and unique focus on the island’s architectural forms. The context of his work remains foursquare behind the show’s theme: from rural scenes to historic properties across the island including a turning point piece in his career, Yellow Buttery on the Water (1991), where he embraces colour. The infinitesimal detail of fine brushwork shows the artist at his best and the distinctive low perspectives lend loneliness to the work.

Pembroke parish is, as the exhibit establishes, problematic; being neither “up country” or “down country”. The show’s mezzanine level serves as an invigorating counterpoint to the exhibit. Dubbed “Other Country”, the literal and metaphorical merge personifying the intangible elements that mark a special part of Bermuda’s character.

The gallery has chosen to avoid images of Hamilton, the subject of recent shows, and depict the capital differently.

The large centrepiece acrylic on canvas, La Marseillaise in Bermuda, by the contemporary Japanese artist Ushio Shinohara, draws attention. What appears at first to be a piece of abstract expressionism in dazzling turquoise and green, gradually reveals its figurative elements.

Look closely, and a latter-day icon of Bermudian transportation emerges in the central form of pink psychedelic plasticity. The accompanying video is instructive about the process of the avant-garde painter.

The contemporary South African/Dutch artist Jacqueline Alma’s impressive panorama in charcoal, Belco 2015, shows the heart of the island’s energy generation.

She transforms the brutally industrial scene of snaking pipework and smokestacks into something strangely beautiful.

You leave the gallery having seemingly walked a memorable journey the length of Bermuda.

You’ll want to revisit this fun exhibition. Masterworks has brought a touch of magic to a well-thought-out show that runs until its 30th anniversary in 2017.