Chester is a holiday and resort destination, with many seasonal and year-round estates and mansions. As a result, it is one of the wealthiest communities in the province. The nearby waters of Mahone Bay and its numerous islands are well known for yachting and have made the Chester Yacht Club into a cruising destination.
Chester was a filming site for the TV series Haven and for parts of The Curse of Oak Island.
- Visitor information is available at the Station 20 shop (see "Buy" section).
The French had been present in Acadia since the early 1600s, but when the British expanded into the area in the 1700s, Acadian settlements on the South Shore where few and tiny. After the Expulsion of the Acadians, the British wanted to repopulate vacated lands, and offered land grants to colonists from New England, which was experiencing a population explosion. In 1761 New England Planters were granted lands in the Chester area, then called Shoreham.
During the American Revolution, Nova Scotia was invaded regularly by American Revolutionary forces and privateers, including the 1782 Raid on Chester. During this time some of the New England immigrants were not loyal in the conflict: village founders Timothy Houghton and John Seccombe were charged with sedition, and military officer Jonathan Prescott was suspected of being an American sympathizer.
During the 1800s, Chester was an important site for coastal commerce, with economic activities including lumbering, shipbuilding, shipping, and fishing.
The most efficient way to reach Chester, and Chester Basin is by car. Rental cars are available at the Halifax International Airport.
A ferry from the village provides a schedule of daily trips to Big Tancook Island and Little Tancook Island.
- Chester Playhouse. The Chester Playhouse is a charitable organization for the promotion of performing arts. The building is a cinema built in 1939 and converted in 1963. Its capacity is 176. The theatre has a year-round program with a variety of performance types.
- Chester Garden Show and the House and Garden Tour. in the last weekend of July. Also that weekend is the Bonnie Lea Lobster benefit.
- Lordly House Museum, 133 Central Street, ☏ . Late Jun to mid-Sep: Tu-Sa 10AM-4PM. A fine example of Georgian architecture (c 1806). Lordly House was the family home of Charles Lordly, a prominent merchant, an entrepreneur, and the first municipal clerk. The museum showcases historical displays, and houses a local genealogy collection. A park and playground surround the museum. By donation.
- Boating: There are a number of public boat launch sites around Mahone Bay. The waters are fine for kayaking and sailing. The Chester Yacht Club hosts Chester Race Week, where keelboats from all over the eastern coast of North America compete during the second week of August.
- Chester Connector: a multi-year trail for walkers and cyclists on an old rail line. Parts of it are shared with motorized recreational vehicles. Access from behind the Station 20 shop.
- Chester Golf Club. On the eastern side of the front harbour. It has 18 holes and views of the harbour.
- The Church Memorial Park is home to the Chester Tennis Club, Eleanor Pew Memorial Rink and Chester Curling Club.
- Station 20 Shoppe and Museum, 20 Smith Road (just off North Street), ☏ . Summer only. The Chester Train Station was built circa 1905 for the Halifax and South Western Railway Company. Today the station houses the Explore Oak Island Display, which provides information about the world’s longest-running treasure hunt. There is a display of pumps and other machines manufactured and designed by a local inventor who is credited with developing the make-and-break engine which heralded the demise of the sail powered fishing boats. There is a Farmers' Market late May to early Oct every Friday from 10AM-2PM, and a craft shop that sells handmade items by local artisans.
- Going Coastal Fine Art and Furnishings, ☏ . A local family-owned and -operated custom furniture store and art gallery selling works by local artists and craftsmen.
- The Kiwi Cafe, 19 Pleasant St, ☏ . Daily 8AM-5PM. Breakfasts, wraps, sandwiches, salads, wine, beer.
- The Rope Loft, 36 Water St, ☏ . Dockside restaurant and pub with a view of the harbour. Seafood, pasta, salad, flatbread pizzas.
- The Stretch Diner, 3758 Highway 3, ☏ . Daily 11AM-7PM. Fish and chips, lobster rolls, diner food.
- The Fo'c'sle Tavern, 42 Queen Street, Corner of Queen & Pleasant Streets, ☏ . Open every day but Christmas Day from 11AM until everyone goes home (the kitchen staff go home at 9PM). Nova Scotia’s oldest pub. Known locally as the "living room" of Chester. Depending on where you sit, you’re in a former grocery store, stable, inn or tavern dating back to 1764.
- Tanner & Co. Brewing, 50 Hiltz Rd, Chester Basin. Opening hours vary. A small brewery in Chester Basin, focusing on traditional German Ale beer styles, and small lot unique beers & beer styles.
- Windjammer Motel, 4070 Highway 3, ☏ . Individually controlled heat, air-conditioning (in some rooms), small fridge, Wi-Fi. Jun 15-Sep 15: single $85, double $95; lower rates in the off-season.
- Mecklenburgh Inn B&B, 78 Queen St, ☏ . Four guest rooms, all with private bath; most have sofas and distant water views. The wide pine flooring has been restored to its original state. Full breakfast. From $149.
- White Gate Inn & Restaurant, 28 Pleasant St., ☏ . Three rooms furnished in classic East Coast style with hand-crafted furniture made locally in Chester. En suite bath. No pets or small children, not wheelchair accessible. Open May to December. The restaurant has an internationally inspired menu, highlighting East Coast ingredients freshly caught and locally sourced.
|Routes through Chester|
|Yarmouth ← Liverpool ←||W E||→ Hubley → Halifax|
|Yarmouth ← Lunenburg ←||W E||→ Jct E → Hubley → Halifax|
|ENDS at N S ← Windsor ←||N S||→ END|