South Shore and Annapolis Valley Restaurants

We’ve compiled the best of the best in South Shore and Annapolis Valley - browse our top choices for Restaurants during your stay.

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  • 1. Cocoa Pesto Bistro

    $$$

    A warm welcome and elegant surroundings provide a great first impression here, but it's the delicious, fresh, and health-conscious cuisine that lingers in memory. The menu changes seasonally, but always includes dry-rub or honey-glazed pork ribs straight from an apple-wood smoker. The bistro's rooms have a minimalist look that nicely balances the heritage building's original architectural features, and a patio provides outside dining in summer.

    494 King St., Windsor, Nova Scotia, BON 2TO, Canada
    902-472–3300

    Known For

    • <PRO>location in a nice old building</PRO>
    • <PRO>some gluten-free options</PRO>
    • <PRO>unpretentious menu ranges from upscale mains to pub favorites</PRO>

    Restaurant Details

    Rate Includes: No lunch Mon. and Tues., no brunch weekdays
  • 2. Fo'c'sle Tavern

    $$

    This rustic midtown spot—a former store, stable, and Nova Scotia's oldest rural inn, dating to 1764—is full of natural pine and local art, and its staff and clientele treat regulars and newcomers like kin. In the windowed front section, a woodstove keeps things warm on chilly nights, and year-round you can order from a menu that's strong on seafood and comfort food. Lighter fare is also served, along with plenty of craft beers.

    42 Queen St., Chester, Nova Scotia, B0J 1J0, Canada
    902-275–1408

    Known For

    • Live music some nights of the week
    • Weekend brunches with lots of choices
    • Craft beers on tap
  • 3. Rebecca's Restaurant

    $$$

    Head to Rebecca's for freshly prepared, flavorful, and beautifully presented dishes. Creamy seafood chowder is a popular starter, while hearty and interesting mains include inventive seafood, meat, and vegetarian choices (vegan on request). Several items can be made gluten free. There's regular live music here, too, and always a nice friendly atmosphere.

    619 Main St., Mahone Bay, Nova Scotia, B0J 2E0, Canada
    902-531–3313

    Known For

    • Local free-range meat and eggs
    • Gigantic and delicious made-from-scratch desserts
    • Lovely view over the water

    Restaurant Details

    Rate Includes: Closed Thurs.
  • 4. The Kiwi Cafe

    $$

    This bright and friendly spot is a Chester community hub, and is a great spot to grab breakfast, lunch, or just coffee and a treat. Everything served is fresh, locally sourced where possible, and absolutely delicious. The attached pantry sells specialty food items, locally-made jams and chutneys, and a selection of take-and-heat meals to go.

    19 Pleasant St., Chester, Nova Scotia, B0J 1J0, Canada
    902-275–1492

    Known For

    • Large bright and sunny patio
    • Outstanding haddock and lobster chowder
    • Excellent mimosas
  • 5. Winegrunt

    $$

    Every dish offered on the small, creative menu is perfectly executed whether it's a French classic like ​Boeuf Bourguignon or a charcuterie board. There's a huge selection of local wines to try, as well as an international wine list, and often live jazz in the evenings. They offer a three-course tasting menu on Thursday (C$25) and brunch on Sundays.  

    43 Water St., Windsor, Nova Scotia, B0N 2T0, Canada
    902-472–2863

    Known For

    • Lively, fun atmosphere
    • Locally sourced ingredients in food offerings
    • Staff are very knowledgeable on wines

    Restaurant Details

    Rate Includes: Closed Mon.–-Weds.
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