Oak Bluffs Restaurants

We’ve compiled the best of the best in Oak Bluffs - browse our top choices for Restaurants during your stay.

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  • 1. Back Door Donuts

    $

    Who needs saltwater taffy when you can have a freshly-baked apple fritter or gooey, buttermilk glazed donut? This is a donut shop with a secret: By day, it's a tucked-away bakery; at 7 pm, they open the back door and sell warm treats to in-the-know fans who line up for the privilege.

    1-11 Kennebec Ave., Massachusetts, 02557, USA
    508-693--3688

    Known For

    • Early evening secret baked treats
    • Apple fritters
    • Buttermilk glazed donuts

    Restaurant Details

    Rate Includes: Closed Tues.; back door portion of business closed from mid-Oct.--May.
  • 2. Biscuits

    $

    There will be a line, but this hole-in-the-wall breakfast joint is a great spot for grabbing a hand-held breakfast sandwich—say, a honey-chicken biscuit—en route to the ferry. If you're not in a rush, nab a table, and peruse the extensive menu featuring Southern favorites like shrimp and grits and chicken and waffles along with stuffed French toast and linguica hash.

    20 Lake Ave., Massachusetts, 02567, USA
    508-693--2033

    Known For

    • Shrimp and grits
    • House-made biscuits
    • Breakfast sandwiches

    Restaurant Details

    Rate Includes: Closed mid-Oct.--Apr. No dinner
  • 3. Lookout Tavern

    $$

    Sometimes, you don't feel like a fifty-dollar, fancy-schmancy entrée—you just want a big, fat lobster roll and a beer, and that's what you'll get at Lookout Tavern. Dig into fresh lobsters from Katama Bay, eight kinds of tacos (beer-battered cod is the best), or sushi and sashimi. Pro tip: Skip the indoor tables and head to one of the stools facing the water—perfect for watching ferries and pleasure boats glide by (and even better with a rum punch in hand.)

    8 Seaview Ave., Massachusetts, 02557, USA
    508-696--9844

    Known For

    • Rum punch
    • Great views of the busy harbor
    • Lobster rolls (served with mayo or sautéed in butter) and lobster bisque

    Restaurant Details

    Rate Includes: Closed Jan.--Apr., No reservations
  • 4. Offshore Ale Company

    $$

    The island's first microbrewery restaurant is quite popular with locals and visitors alike, especially since it is open year-round. There are private wooden booths, a dart board in the corner, and live music year-round. Grab some peanuts from a barrel by the door and drop the shells on the floor; then order from a menu that includes steaks and burgers, chicken, pasta, gumbo, and fish. However, to truly appreciate the beer, try it with one of the wood-fired brick-oven pizzas. There's a nice shaded patio for outdoor dining.

    30 Kennebec Ave., Massachusetts, 02557, USA
    508-693–2626

    Known For

    • Rotating beers on tap
    • Unique pizzas
    • Fish-and-chips

    Restaurant Details

    Rate Includes: No lunch weekdays, Reservations not accepted
  • 5. Red Cat Kitchen

    $$$$

    Standing at nearly 6½ feet tall and covered with colorful tattoos, chef-owner Ben Deforest turns out an extraordinary array of dishes—chorizo-stuffed local calamari, crab and wild mushroom risotto, or truffle arancini—from a tiny kitchen visible from the dining room. Regulars love the funky artwork, thundering tunes, and the irreverent spirit of the place, but no question here: it's the food that keeps them coming back.

    14 Kennebec Ave., Massachusetts, 02557, USA
    508-696--6040

    Known For

    • Frequently changing (sometimes daily) seasonal-based menu
    • Crispy Brussels sprouts
    • Ample portions

    Restaurant Details

    Rate Includes: Closed Nov.--Mar.
  • Recommended Fodor’s Video

  • 6. Sweet Life Café

    $$$$

    Housed in a charming Victorian house, this island favorite's warm hues, low lighting, and handsome antique furniture will make you feel like you've entered someone's home. The cooking is more sophisticated than home style, however: dishes are prepared in inventive ways and change often with the seasons. Ask for the Obama's favorite table (if they're not already occupying it.)

    63 Upper Circuit Ave., Massachusetts, 02557, USA
    508-696–0200

    Known For

    • Superb desserts
    • Outdoor dining by candlelight in a shrub-enclosed garden
    • Locally sourced food

    Restaurant Details

    Rate Includes: Closed Mon. and Tues. and Jan.–Mar. No lunch, Reservations essential

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