Chester, Nova Scotia: Things to Do, Where to Stay & Why It's the South Shore's Best Escape

Tucked along the shores of Mahone Bay on Nova Scotia's South Shore, Chester is one of those rare places that feels like a secret, even though those lucky enough to discover it can't stop talking about it. With its picturesque harbour, world-class sailing, incredible seafood, and a community that pulses with life all summer long, Chester, NS is the kind of destination that gets under your skin and keeps calling you back.

It's also where we've put down roots. At Dukes Compass, we hand-pick a small collection of properties in and around Chester so our guests can experience the village the way we know it — slowly, comfortably, and with a great cup of coffee in hand. Whether you're sailing in for Race Week, planning a long family weekend, or quietly escaping the city for a few days, this guide will help you make the most of it.

Chester Race Week — Where to stay in Chester NS

If you're visiting between August 12 and 15, 2026, you're in for a treat. The Atlantic Yacht Sales Chester Race Week (formerly Helly Hansen Chester Race Week) is one of the oldest and most celebrated sailing regattas in North America. Hosted by the Chester Yacht Club, it's Canada's largest keelboat regatta, drawing more than 130 boats and 1,300-plus sailors from across North America to Mahone Bay each August. Chester Race Week The harbour comes alive with coloured sails, laughter, and friendly competition. Whether you're racing, crewing, or simply cheering from the shore with a cold drink in hand, Race Week is unlike anything else on the East Coast.

A word of advice from us: book your stay early. Race Week is the busiest week of Chester's year and our properties typically fill six to nine months in advance. If you're even thinking about being here for it, lock something in soon.

Things to do in Chester Nova Scotia

Chester is a sailing town through and through. Mahone Bay is dotted with over 100 islands, making it one of the most beautiful cruising grounds on the Atlantic coast. Whether you're an experienced sailor chartering a boat, a beginner taking your first lesson, or someone who just wants to kayak between the islands on a glassy summer morning, the water here is endlessly inviting.

The Chester Yacht Club has been the social hub of the local sailing community for generations. For a different kind of island day, hop on the Tancook Island ferry  from the Chester waterfront, a short crossing to a pair of lost in time islands with walking trails, rocky shorelines, and famously good cabbage farms (yes, really). Most of our guests tell us their favourite mornings are the slow ones, coffee on the porch, watching the boats wake up before they head out themselves.

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Where to Eat in Chester, NS

Chester's food scene punches well above its weight. Here are a few must-visits:

The Kiwi Café is a Chester institution — a beloved spot for fresh, relaxed dining with a loyal local following. It's the kind of place where the coffee is great, the food is honest, and you'll want to linger far longer than planned. Perfect for a slow morning or a lazy lunch.

The Fo'c'sle Tavern - built in 1764, this is Nova Scotia's oldest pub. Laid-back atmosphere, honest pub fare, and a Chester rite of passage.

Il Ferramenta- A Roman-style pizzeria on Duke Street, turning out crisp, slow-fermented pizza al taglio with seriously delicious toppings. Perfect for a casual dinner after a day on the water, and an easy walk from the village. Located right beside Duke's Compass.

The Rope Loft, for fresh seafood You really can't go wrong in Chester. The lobster, haddock, and scallops pulled straight from the cold Atlantic waters are exceptional, look for local fish shacks and daily catch specials wherever you eat. There's nothing quite like cracking a lobster with a harbour view.

The Chester Farmers' & Artisan Market and shops are also worth exploring for artisan cheeses, fresh produce, and Nova Scotia wines and ciders that make for perfect evening sundowners back at your accommodation. Every Friday starting the end of May.

Exploring the Village of Chester Nova Scotia

Chester village itself is wonderfully walkable, which is one of the reasons we love placing guests close to the heart of it. Wander the charming streets lined with heritage homes, pop into independent boutiques and galleries (the Chester Art Centre and Jim Smith's Pottery are local favourites), or simply sit at the waterfront and watch the boats go by. The Back Harbour Trail offers a beautiful nature walk through coastal forest with stunning bay views, most of our guests do it at least once.

Sensea Nordic Spa 

Nova Scotia's first Nordic spa, set in the woods just outside the village — is the perfect way to unwind after a day on the water. Thermal pools, saunas, and forest bathing make it a year-round highlight, and an easy walk or short drive from most of our properties.

Chester Golf Club

18-hole course with panoramic views of Chester Harbour and the islands.

Rum Runners Trail 

If you've brought your bike, theruns 119 km from Halifax through Chester all the way to Lunenburg, perfect for a half-day ride.

The three iconic churches of Mahone Bay

— Just a short drive away,are one of Nova Scotia's most photographed scenes, beautiful at any time of year, and absolutely magical reflected in the harbour on a still morning. The town of Mahone Bay itself is well worth an afternoon of exploring, with great shops, galleries, and cafés.

UNESCO World Heritage town of Lunenburg

— is only about 30 minutes away and is absolutely not to be missed. Its colourful, perfectly preserved 18th-century streetscapes and rich maritime history make it one of the most remarkable towns in all of Canada.