Discover Chester: Sailing, Culture and Recreation

Chester offers a range of reasons to visit: sailing, culture and waterfront recreation. When choosing a vacation rental, it helps to first decide on your travel dates and interests. Should your trip coincide with a regatta, include a ferry ride, or leave room for sports and performances? The answers give your stay a clear focus.

Regatta, Ferry and Waterfront Spots

Helly Hansen Chester Race Week is an annual four-day keelboat regatta hosted by the Chester Yacht Club in the village of Chester. The program includes public events featuring live music, food and yacht races, as well as regatta seminars led by internationally renowned sailors, tacticians, boatbuilders and sailmakers. Individual activities may change. If Race Week is the reason for your trip, check the latest dates and program in advance.

The Tancook Island Ferry runs daily year-round on a set schedule. It departs from Chester and serves Little Tancook Island and Big Tancook Island. If you plan to take the ferry, coordinate your trip with the current schedule. Freda's Beach, a swimming spot, is located at Front Harbour; the Lido Pool is on the shore of Chester's Back Harbour. This gives you the option of including two distinct waterfront spots in Chester in your plans, without confusing them with the regatta program.

Chester Golf Club has been in operation since 1914. The course is par 70 and offers views of the sea and Chester Harbour. Course conditions may change; take this into account if golf is part of your travel plans.

Sports, Play and Culture

Chester Skate Park is a 14,500-square-foot facility with street and bowl areas. Events such as skateboarding and BMX competitions are held there annually. Lordly Park adds a playground with slides, climbing bars and swings to the range of sports and recreation options. The two places cater to different leisure interests: a skate park with competitions and a playground with specific play equipment.

Chester Playhouse showcases local, national and international artists, performances and other artistic content. If you are interested in the performing arts as well as regattas and outdoor activities, you can take this cultural offering into account when choosing your travel dates. Zoé Vallé Memorial Library offers free Wi-Fi; meeting rooms can also be booked there.

Plan Your Stay Around Your Interests

Travel dates and interests are a good starting point when looking for a vacation rental in Chester. Race Week takes place annually over four days, while the ferry runs daily year-round and follows a schedule: it is worth checking the latest information for both, but for different reasons. If the skate park, golf, beach or cultural offerings are a higher priority, you can make those interests the focus when planning your days.

In the Wider Destination of Lunenburg County

Nature and culture also shape potential travel interests in the wider destination of Lunenburg County. Holden Lake Wilderness Area protects approximately 1,700 hectares of older mixed forest in the Gold River watershed, surrounding much of Holden Lake. The area includes 10 kilometres of lakeshore and about 4 kilometres along the Gold River. Indian Path Common offers 7 kilometres of natural walking trails in a series of loops and is a 350-acre reclaimed Acadian forest area.

Rissers Beach Provincial Park offers camping and swimming at a sandy beach. Its described features also include interpretive panels and a boardwalk through a salt marsh. Current operating conditions may change; check them before visiting. These natural areas are examples from Lunenburg County and are not additional features of Chester itself.

Discover more destinations: Western Shore, Bridgewater, Hubbards, Barss Corner, Lunenburg, Mahone Bay

Back to the wider travel guide: Lunenburg County.