Like so many other towns in Nova Scotia, Chester is best seen from your car. But unlike other towns, where the center of gravity seems to be in the commercial district, here the focus is on the graceful, shady residential areas that radiate out from the tiny main street.
In your rambles, plan to head down Queen Street to the waterfront, then veer around on South Street, admiring the views out toward the mouth of the harbor. Continue on South Street past the yacht club, past the statue of the veteran (in a kilt), past the sundial in the small square. Then you'll come to a beautiful view of Back Harbour. At the foot of the small park is a curious municipal saltwater pool, filled at high tide. On warmer days, you'll find what appears to be half the town out splashing and shrieking in the bracing water.
Some creative shops are beginning to find a receptive audience in and around Chester, and there's good browsing for new goods and antiques both downtown and in the outlying areas. One such shop is the Village Emporium at 11 Pleasant St. (tel. 902/275-4773), an eclectic clustering of folk-arty lavender soaps, simple pottery, knit purses, and the like; it's in the same building as the Kiwi Café.
For an even slower pace, plan an excursion out to the Tancook Islands, a pair of lost-in-time islands with 200 year-round (as opposed to year-old) residents. The islands, accessible via a short ferry ride, are good for walking the lanes and trails. There's a small cafe or two on Big Tancook, but little else to cater to travelers. Several ferry trips are scheduled daily between 6am and around 6pm. The ferry ties up each night on one of the islands, however, so don't count on making a late trip back to the mainland. (But there's also an inn on Big Tancook, if you're inclined to stay over.) Ferry tickets are C$5 round-trip, free for children under 12.
In the evening, the intimate Chester Playhouse, 22 Pleasant St. (tel. 800/363-7529 or 902/275-3933; www.chesterplayhouse.ca), hosts plays, concerts, a summer theater festival, and other high-quality events from March through December; it's a town institution, and absolutely a must-visit if you're a theater or folk music buff. Theater festival tickets are usually around C$25 per person for adults, cheaper for children; musical performance ticket prices vary. Call or check the Playhouse's website for a schedule or to purchase tickets.
The local library at 63 Regent St. is a great place to check out local history, too. It was a gift from a New Yorker in memorial of her sister, Zoé Vallé Lightfoot (related to Josiah Bartlett, who signed the U.S. Declaration of Independence).
Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.