Chester is situated about 65 km southwest of Halifax in Nova Scotia's South Shore region.
The most efficient way to reach Chester, and Chester Basin is by Car. Rental cars are available at the Halifax International Airport or from many locations in Halifax or Dartmouth. If you are driving to Chester, you can either take Highway 103 south from Halifax, which will mean about a 45 minute drive to reach Chester (Exit number 8). The alternative is to take the much more scenic St. Margaret's Bay Road, which follows the coastline and passes through beautiful seaside towns like Hubbards on it's winding route to Chester. As you can imagine, this route is a bit longer (plan for at least an hour and a half), but the payoff are some spectacular vistas as you wind along the south shore of Nova Scotia.
If you don't have a car, another alternative is the Acadian lines bus service that leaves from Halifax along the South Shore of Nova Scotia Daily (Booking inquiries: 1-800-567-5151).
Without a car your options will be seriously limited in Chester. This small town does not have an existing form of public transport.
If you are really in a pinch to get somewhere and you don't have a car (or a friend to call), then there is a taxi service that operates a few cabs in the south shore of Nova Scotia (South Shore Taxi - 1 902 277 2727). Be aware that there are a limited number of available cars and book ahead.
The main draw in Chester is of course the views of the beautiful St. Margaret's Bay. This island dotted cove is a nautical dream, and when in the village of Chester, you will never be more then a short distance from a viewpoint overlooking the ocean.
Other than this obvious draw there are many other hidden gems to be found. In the center of town there is a very nice little theatre, the Chester Playhouse. Located on the aptly named Pleasant Street, the playhouse often runs local small budget productions by local artists throughout the summer. You can check the website for more information (Chester Playhouse). A short drive (10mins) outside Chester to the north, you can also find Graves Island. The island is connected to the mainland via a driving bridge. Once there you can wander freely and enjoy the calm serenity and scenery on this island park.
Finally, the ocean views may be what attract visitors to Chester, but it's the coastal charm that keeps them coming back. Take time to walk the streets and look at the beautiful Cape Cod style houses, many of which are protected historic properties dating to the 19th century.
This villiage is really made for relaxing strolls and lazy afternoons. But if you feel like you need to plan some activities, there are plenty of options:
Drive. If you have a car, then you should take advantage and drive the South Shore. Heading south from Chester along St. Margaret's Bay Road you can continue through the towns of Chester Basin, Mahone Bay, Lunenburg, Bridgewater, and eventually Liverpool. To do all of these in one day would be a serious drive, as you will want to stop and take some time to enjoy each, but it would certainly be a day well spent. Alternatively, you can head north in the direction of Halifax (if you didn't already arrive this way) and follow the St. Margaret's Bay road in that direction through East Chester, Blandford, Hubbards, and Peggy's Cove. Finally, if you want to see something less coastal you can take highway 14 (called "Windsor Road" by locals from Chester and "Chester Road" by locals from Windsor) through to the town of Windsor, and see more of countryside that supports the farming and lumber economies in Nova Scotia.
Take the Tankook Ferry from the terminal on the public warf on Water Street. If you are interested in visiting one of the islands you see off the coast of Chester. With stops at both Big and Little Tankook islands, you will have an opportunity to see what island life is like. Be aware that the ferry generally has 2 runs from each stop every morning and 2 every afternoon, with last ferry generally leaving the island at 4:30pm!
Beach. If you are looking to get in the water, there are several options. In Chester, there is a small public beach located on Peninsula Rd. next to the bridge connecting the penninsula to the mainland. Other than that you will have to leave Chester to find any sandy beaches, the closest (and nicest by my estimation) is Queensland Beach located off St. Margaret's Bay Rd. close to Hubbards (about 25-45minutes drive depending on route).
Chester Race Week. If you have the opportunity to be in Chester in early to mid August, then you are in luck. Every year, the village hosts Chester Race Week, an international sailing regatta that attracts hopeful competitors from all along the eastern coast of Canada and the United States as well as some competitors from further abroad. The races themselves are always exciting, but the highlight is the celebration on the last day, which is headlined by festivities hosted at the local Yacht Club located on South St.
Chester Golf club. If you are a golf fan, look into the Chester Golf Club (located on Golf Course Rd, of course), the challenging (but not too challenging) course, offers some of the best ocean vistas the village has to offer.
Finally, there are of course plenty of other things to do in town, and with a little research you will be able to plan a relaxing, fun, and maybe even adventurous holiday.
You will find plenty of your standard nautical novelty souvenirs in Chester, as you will in any of the towns that dot the South Shore. However, if you have a little extra to spend, and want to get something special, look to some of the local artists making hand made crafts. Some of the more notable options are found along Pleasant and Duke Streets. The Valverde Studio Gallery, Chez Glass Lass, and Light my Fire studio have all become particular favorites of visiting tourists.
There are plenty of great places to eat in Chester, and if you were so inclined, you could certainly pass a vacation sampling the different restaurants, pubs, bakeries, and cafes the villiage has on offer. A few that should not be passed up are:
The Rope Loft. Found on Water Street, on a dock jutting out into the front harbour, this seasonal pub/restaurant is a great place to relax at night enjoying a pint of Keith's and a some local seafood.
The Fo'c'sle Tavern. The dining area has been renovated in the last few years, but this tavern still kept all it's charm. More popular with locals than the Rope Loft, this centrally located tavern on Queen st. offers many of the same options as the Rope loft with a more pub like feel.
The Kiwi cafe. If you are looking for a light lunch or a coffee and a snack, this bright and airy cafe is a great stop. It is found on Pleasant st. across from the Chester Playhouse.
Julien's Bakery. If you are dreaming of something a bit more European, stop into Julien's where they offer up freshly baked pastries, breads and deserts every day. Across from the Fo'c'sle on Queen st.
Like any small town in Nova Scotia, Chester has a few watering holes available to the weary traveller and friendly local alike.
The Fo'c'sle Tavern. known locally as the "living room" of Chester, this tavern, which also has a pretty nice dining room, doubles as an after work gathering place for locals looking to unwind after a day of work. You can usually find good conversation, friendly people, and maybe even some live music.
Feaver & Co., 4080 Hwy 3, Chester, Nova Scotia B0J1J0, ☎ 902-277-3332. This sports bar is a reletively new addition to Chester. it is a great place to watch the hockey game and possibly catch a live music act.
Haddon Hall, Haddon Hill Chester, NS, Canada. This Luxury Inn was built in 1905 in the Victorian style. Today the lucky travellar who can afford it will be treated to spectacular views from it's prime location on Haddon Hill, overlooking St. Margaret's Bay.
WindJammer Motel, 4070 Highway#3 Chester, NS B0J 1J0, Canada, ☎ 1 902-275-3567. This budget motel is within walking distance of the center of the village. Don't expect much, but if you are trying to save some money, this motel is well situated to allow you to enjoy your time in Chester.
The Chester and Area Visitor Information Center is located on 20 Smith Road in Chester, in a converted ralway station. The staff there can provide you with information on events and attractions in the area.
It is recommended that anyone visiting Chester plans to take a few drives and visit some of the other towns along the South Shore. Some of the higlights of any such trip would include the beautiful rocky coastlines of Peggys Cove, The UNESCO world heritage village of Lunenburg, or the quaint small town of Liverpool