Experience All This Place Offers
Food, Glorious Food
In Chester, dining is part of the getaway. Make a reservation at The Rope Loft for waterfront seafood and sunset views, then linger over a second glass like you have nowhere else to be.
Back at Highlander House, you can finish the evening on the dock, a nightcap in hand, with the harbour lights and the tide doing their quiet work.
Tastes of Nova Scotia
In Chester, a good drink is part of the rhythm. Start your day with coffee from The Kiwi Café, wander the village at an unhurried pace, then come back to Highlander House and enjoy it on the dock as the harbour wakes up.
Later, raise a glass at the Fo’c’sle Village Pub for classic Nova Scotia character, or settle into Sunroom for cocktails, then return to your safe harbour for a quiet sip by the sea.
So Much To See and Do
Chester is made for slow, beautiful days. Catch a show at the Chester Playhouse, then stroll the village and harbourfront where sailing culture is part of the scenery.
Spend an afternoon on the Rum Runners Trail or exploring the coast and nearby beaches, then come back to Highlander House for golden hour on the dock, watching the boats drift home to the bay.
Get In The Local Spirit
To really slip into the Nova Scotia spirit, get out on the harbour and let the day unfold the way it used to, salt air, calm water, and a little music carried on the breeze.
Book a boat outing, bring a bottle of something good, and lean into the charm, a guitar, a few old shanty songs, and the easy rhythm of Chester on the water. Then come back to Highlander House, drop anchor for the night, and let the harbour lull you into a slower pace.
Sensational Sunsets
Sunsets in Chester feel like a private show, the harbour turns to glass, the sky warms to gold, and the boats slip home in silhouette.
At Highlander House, you don’t have to chase the view because you have the best seat in the house right here. Just step onto the deck or down to the dock, pour a drink, and watch the South Shore fade into evening from your own exquisite safe harbour.