Chester looks like the kind of place where sailors have retired to tinker with boats for a century, and that is more or less true. It sits on a protected corner of Mahone Bay, with hundreds of small islands scattered across the water in front of it, and wealthy New Englanders began building summer houses here in the nineteenth century after settlers from the American colonies founded the town around 1760. The result is a handsome village of white clapboard and tall trees, with a few shops, a playhouse and a yacht club that organises Chester Race Week every August.
The water is the main attraction. A ferry runs from the area to the Tancook Islands, where German-descended families have fished for generations and made sauerkraut a local speciality. Oak Island, a short distance down the coast, is the setting of Canada's best-known treasure legend. For two centuries people have dug a pit there, convinced that something valuable lies underneath. Nobody has found it, and the story itself is the chief treasure.
The road is part of the Lighthouse Route, and this section is among the gentlest on the coast. Instead of high cliffs you get low, wooded headlands, small bays and rocky coves, with spruce and fir pressing against the pavement. The curves are pleasant rather than demanding, and the corners come with a view of the water around every other bend. Fog can drift in and make the surface damp, so ease off and trust your tyres. Traffic builds on summer weekends, when cyclists and visitors fill the road, so a midweek morning is best. September, when the summer crowds have thinned and the water is still warm, is my favourite month.
Chester has about fifteen hundred residents, which means fuel and groceries exist but options are limited. The larger towns nearby are Lunenburg and Bridgewater, and Halifax is around an hour to the east, so top up if the gauge is low. Sit on the waterfront with a coffee, listen to the halyards ticking against masts and let the pace of the place settle in.