Connecticut River Valley
The Connecticut River, New England's longest, flows southwards 410 miles from its humble source at Fourth Connecticut Lake, just 300yd from the Canadian border. It forms the state boundary between Vermont and New Hampshire, before snaking its way through Massachusetts and Connecticut until it meets the Atlantic at Long Island Sound.
As you wander around Yale University's venerable campus, admiring the gorgeous faux-Gothic and Victorian architecture, it's hard to fathom New Haven's struggle to shake its reputation as a dangerous, decaying seaport. Connecticut's second-largest city radiates out from pretty New Haven Green, laid by Puritan settlers in the 1600s.
Connecticut's capital, one of America's oldest cities, is famed for the 1794 birth of the lucrative insurance industry, conceived when a local landowner sought fire insurance. Policy documents necessitated printing presses, which spurned a boom in publishing that lured the likes of Mark Twain, Harriet Beecher Stowe and Wallace Stevens.
The rolling hills in the northwestern corner of Connecticut are sprinkled with lakes and dotted with forests and state parks. Historic Litchfield is the hub of the region, but lesser-known Bethlehem, Kent and Norfolk boast similarly illustrious lineages and are just as photogenic. An intentional curb on development continues to preserve the area's rural character.
A skyline of masts greets you as you arrive in town on US 1. They belong to the vessels bobbing ever so slightly in the postcard-perfect harbor. There's a sense of self-satisfied calm and composure in the air – until suddenly a heart-stopping steamer whistle blows, followed by the cheerful cling of a drawbridge bell. You know you've arrived in Mystic.
During its golden age in the mid-19th century, New London, then home to some 200 whaling vessels, was one of the largest whaling centers in the US and one of the wealthiest port cities. In 1858 the discovery of crude oil in Pennsylvania sent the value of whale oil plummeting and began a long period of decline for the city, from which it has never fully recovered.
The Gold Coast
The southwestern corner of Connecticut, otherwise known as the Gold Coast, was once home to potato farmers and fishermen until 19th-century railroads brought New Yorkers north. With their blue-chip companies they transformed Fairfield County into one of the wealthiest regions in the USA, with the affluent town of Greenwich at its heart.
Five miles east of Mystic on US 1, Stonington is Connecticut’s oldest ‘borough’ and one of the most appealing towns on the coast. Laid out on a peninsula that juts into Long Island Sound, the town's compact footprint is scattered with photogenic 18th- and 19th-century houses, many of which were once sea captains' homes.
Travelling south from New Haven, you enter Fairfield County via affluent Westport, dubbed 'Beverly Hills East' for its popularity as a retreat for artists, writers and film stars. Despite its links to the rich and famous, the town otherwise bears no resemblance to Beverly Hills whatsoever.