Follow along as we head to Chester
Follow along as we explore Nova Scotia’s South Shore, showcasing our regional pride through its celebrated lighthouses, stunning beaches, and delicious local eateries
This week, we head to the oceanside sailing town of Chester!
A little about the town!
Chester is a picturesque coastal village that epitomizes maritime charm and relaxed elegance. The town is defined by its historic, tree-lined streets, beautifully preserved architecture, and stunning ocean vistas. Deeply rooted in seafaring traditions, it serves as a vibrant hub for the regional sailing community, where the harbour is constantly dotted with masts and hulls. Beyond its nautical identity, the village maintains a tranquil yet sophisticated atmosphere, blending a rich cultural heritage with the natural beauty of the South Shore coastline, making it a peaceful haven for both residents and travellers seeking coastal serenity.
Things to see and do
Take a tour!
As you stroll along the hilly, tree-lined streets, you will pass well-preserved 18th and 19th-century architecture, ranging from classic New England-style saltbox houses to grand summer estates. The town's artistic community is on full display through its independent art galleries, artisanal craft shops, and, of course, the famous Chester Playhouse, which serves as a cultural hub for live performances.
Take in a show!
Taking in a live performance at the Chester Playhouse stands as a highlight of any visit to the South Shore. Operating on Pleasant Street since 1938, this historic hub was beautifully rebuilt following a 2021 fire, resulting in a state-of-the-art facility that seamlessly marries historic charm with modern acoustic and lighting technology. With a cozy main theatre seating up to 175 patrons, there isn't a bad seat in the house. Audiences are treated to a dynamic, year-round lineup that spans world-class live theatre, independent films, stand-up comedy, and an array of musical performances
Take a dip!
The Lido Pool is a unique outdoor saltwater pool built directly along the edge of the village's back harbour. Originally constructed as a Canadian Centennial project in 1967, this community landmark fills its basin with natural ocean water drawn right from the sea. Public swimming is entirely free for both residents and visitors, making it an accessible spot for recreation. The layout features a gradual depth with friendly steps perfectly suited for all ages, and the facility ensures a safe, comfortable experience by providing certified lifeguards, public washrooms, and relaxing benches on-site.
Take a shot!
For the duffers touring the shore, a stop in Chester is a must! The Chester Golf Club is a premier 18-hole golf facility, operated as a non-profit, situated on the southwest shore of Chandlers Cove, offering breathtaking, unobstructed ocean vistas from every hole. Originally established as a modest 9-hole course in 1914 on land donated by the local Pew family, this par-70 layout spans 6,072 yards and poses a fun yet formidable challenge to golfers of all skill levels, particularly when the Atlantic winds pick up. Public players are welcome.
Beyond the fairways, the facility features a highly rated clubhouse restaurant that does not require a membership, serving up celebrated East Coast staples like fresh lobster rolls and their famously superb seafood chowder to golfers and sightseers alike.
Take a hike!
A hiking trip to Castle Rock, near Chester, offers an moderately challenging adventure featuring a flat approach followed by a steep climb. The round-trip journey spans roughly 8.5 to 9.4 kilometres and takes about 3 to 4 hours to complete on foot. It begins with an easy, flat 3.2-kilometre walk or bike ride along the gravel Chester Connection Trail, passing Labrador Lake. From there, the trail turns into the woods, shifting to a steeper, rugged 1.3-kilometre uphill climb over dirt paths, rocks, and tree roots. Near the summit, hikers can choose between easier, wider paths or a steep, narrow single-track route, though all paths culminate in a short, hands-on rock scramble to reach the top. Reaching the summit rewards you with breathtaking, panoramic 360-degree views of the sparkling waters and green islands of Mahone Bay.
Worth noting: To undertake this excursion, visitors must park at the designated East River Trail Parking Lot on Highway 329, as there is no parking at the trailhead itself. Many adventurers choose to bring bicycles to quickly traverse the flat first leg, locking them at the base of the hill before ascending. Because this is a rugged wilderness trail with no washrooms or trash bins, it is crucial to pack out all waste, wear sturdy footwear for the rocky terrain, and perform a thorough tick check afterward
Take a cruise!
Adding a trip to Chester to your South Shore itinerary opens the door to the ultimate coastal adventure: a completely free ferry cruise directly to the breathtaking Tancook Islands! Departing right from the heart of the village, this 50-minute voyage across the waters of Mahone Bay serves as a budget-friendly mini-cruise, treating you to sweeping ocean views, historic lighthouses, and playful harbour seals before you even step foot on land. Stroll down tranquil gravel roads, beachcomb for rare sea glass, and unwind at cozy local bistros. Whether you choose to explore these coastlines on foot or pedal your way through maritime beauty, this excursion transforms a simple day trip to Chester into a multi-layered, and unforgettable East Coast escape
Big Tancook Island
We’ve definitely worked up an appetite. Fuel up on outstanding locally roasted coffee, artisanal baked goods, and celebrated seafood chowders before or after your coastal adventures…
Where are we eating?
The Rope Loft: A beautiful waterfront restaurant on Front Harbour known for its deck views, light-cream shellfish chowder, and fresh Atlantic seafood.
Fo'c'sle Village Pub: Celebrated as Nova Scotia's oldest pub, offering a cozy tavern atmosphere with 16 beers on tap, hearty pub features, and live music on Saturdays.
The Kiwi Cafe: A beloved, vibrant spot perfect for breakfast or lunch, praised for its seafood chowder, fresh salads, and delicious cookies.
The Jib Coffee House: a cozy place, with rustic charm, offering a unique and eclectic mix of flavours. Enjoy excellent local coffee, weekend brunch and Asian cuisine.
The Sunroom Restaurant & Inn: a bright, cozy seaside spot in Chester, offering seasonal chef-inspired dining and charming boutique accommodations. A great fine-dining option - but be sure to make a reservation!
Fo'c'sle Village Pub
When one day is not enough! Spoiler Alert – one day is never enough.
Extend your visit with a stay at one of Chester’s unique accommodation options.
Mecklenburgh Inn: Situated right in the heart of the village on Queen Street, this 1902 Victorian bed and breakfast is perfect for an authentic in-town experience. It features shabby-chic rooms, sea views, balconies, and a lovely garden deck, and is praised for its hospitality and divine, homemade hot breakfasts.
Gray Gables Bed and Breakfast: Located just minutes outside the core village on Graves Island Road, this cozy property offers a quiet, immaculate, and comfortable retreat close to local landmarks. Guests enjoy access to a relaxing on-site hot tub, delicious breakfasts, and a prime location overlooking Graves Island
The Dordéan Suites of Chester: Nestled on Windsor Road just a short distance from the town centre, this accommodation provides a private, nature-oriented stay. It offers secluded, quiet suites outfitted with fully equipped kitchens, private hot tubs, complimentary snacks, outdoor fire pits, and beautiful forest views.
The Dordéan Suites
After an action-packed, tour of the town, it's time to relax and unwind. Our next stop has to be...
SENSEA Nordic Spa - Nova Scotia’s premier thermal wellness destination, located in a secluded lakeside forest in Chester. This year-round outdoor sanctuary features a traditional hydrotherapy circuit of hot baths, cold plunge pools, and Finnish saunas designed to stimulate the senses. Guests can customize their visit with premium enhancements, including targeted massage therapy, organic facials, and overnight nature accommodations directly on site. Visit their website to for more details and to book your getaway. www.sensea.ca
FUN FACT! - Many of the places we mentioned were used as backdrops in the recent ACORN TV series, "You're Killing Me", starring Brooke Shields and Tom Cavanaugh.
Give it a watch and see how many you can spot! Let us know in the comments!
What are we wearing to Chester? Click the image below.
