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Terrace Rooftop Dining

Terrace Rooftop Dining

Restaurant / Food & DrinkPlymouth

Perched above historic Plymouth at 150 Water Street, Terrace Rooftop Dining pairs sweeping waterfront views with a scratch kitchen rooted in New England. Graze on cold-water oysters, crispy Spanish octopus, and bang bang shrimp, then settle into braised short rib, lobster fettuccine, or pan-roasted salmon. The viral Martini Tree pours twelve hanging cocktails, espresso martinis included, while boozy weekend brunch keeps this Plymouth rooftop bar buzzing above it all.

150 Water St, Plymouth, MA 02360

The Back Door at The Homeport

The Back Door at The Homeport

Restaurant / Food & DrinkChilmark

Menemsha's beloved casual raw bar and takeout counter — tucked around the back of the iconic Homeport Restaurant since 1930. Order lobster rolls, bowls of chowder, fresh oysters, and chilled shrimp steps from the harbor. Outdoor patio seating with harbor views. Open daily 11am–5pm. The perfect quick waterfront lunch on Martha's Vineyard.

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The Pinehills · Plymouth · Massachusetts

512 North Rd, Chilmark, MA 02535

The Black Dog Bakery

The Black Dog Bakery

Coffee / Cafe / BakeryTisbury (Vineyard Haven)

The iconic Black Dog Bakery in Vineyard Haven — pastries, coffee, donuts, and baked goods. Classic MV stop with the famous vintage Black Dog sign inside.

14 Main St, Plymouth, MA 02360, USA

The Black Dog Dockside Cafe

The Black Dog Dockside Cafe

Restaurant / Food & DrinkOak Bluffs

You'll love the grab-and-go ease of The Black Dog Dockside Cafe, tucked right at the Oak Bluffs ferry terminal and perfectly positioned for visitors arriving on island or heading back to the mainland. This freshly renovated takeout spot brings all the beloved Black Dog quality to a quick, casual format — think specialty coffee drinks, chopped bagels, smoothies, cold-pressed juices, hearty sandwiches, and fresh baked goods made to order. The menu builds on Black Dog classics with bright, modern twists that make it easy to fuel up fast without sacrificing flavor. It opens early, runs daily, and accepts online ordering — making it the ideal first stop when you step off the ferry and want something delicious in hand before exploring everything Oak Bluffs has to offer.

12 Circuit Ave Ext, Unit 3, Oak Bluffs, MA 02557

The Black Dog Pub

The Black Dog Pub

Restaurant / Food & DrinkTisbury (Vineyard Haven)

You'll find yourself stepping back into Martha's Vineyard history the moment you walk through the doors of The Black Dog Tavern — the island's most iconic restaurant, perched on the edge of Vineyard Haven Harbor since 1971. This beloved waterfront landmark serves breakfast, lunch, and dinner with unmatched harbor views from its rustic, wood-beamed dining room and open patio. The menu leans into New England classics: fresh local seafood, chef-crafted entrées, homemade desserts, and a full bar. On summer Friday evenings, live music drifts across the water. Whether you're grabbing breakfast before the ferry or lingering over dinner at sunset, the Tavern delivers that rare combination of casual warmth and genuine Cape and Islands tradition that keeps visitors coming back year after year.

20 Beach Street Ext, Vineyard Haven, MA 02568

The Blended Berry of Cape Cod

The Blended Berry of Cape Cod

Coffee / Cafe / BakeryBuzzards Bay

The Blended Berry is a bright, health-forward juice bar on Main Street in Buzzards Bay serving handcrafted açaí bowls, smoothies, fresh-pressed juices, and lighter bites like avocado toast and oatmeal bowls. The shop takes allergen concerns seriously with dedicated peanut-free equipment. A refreshing stop on the gateway to Cape Cod.

283 Main St, Buzzards Bay, MA 02532

The Chart Room

The Chart Room

Restaurant / Food & DrinkBourne

Tucked into Kingman Yacht Center on Red Brook Harbor in Cataumet, this seasonal waterfront landmark serves fresh seafood from a converted barge with original timber beams and a lawn of Adirondack chairs facing the boats. The Mudslide built on Baileys, Kahlua and vodka is the stuff of legend, the lobster roll is off-menu so you have to ask, and the piano bar keeps things lively after sunset. For the summer crowd that comes for harbor views and famous drinks.

1 Shipyard Ln, Cataumet, MA 02534

The Homeport Restaurant & Oyster Bar

The Homeport Restaurant & Oyster Bar

Restaurant / Food & DrinkChilmark

A Menemsha institution since 1930, The Homeport Restaurant & Oyster Bar is the quintessential Martha's Vineyard waterfront dining experience. Fresh oysters, lobster, and local seafood served on a sunset-facing patio overlooking Menemsha Harbor. BYOB. The kind of meal you plan your whole MV trip around.

512 North Rd, Chilmark, MA 02535

The Lanes Bowl & Bistro

The Lanes Bowl & Bistro

Restaurant / Food & DrinkMashpee

Rolling since 2013 at Mashpee Commons, The Lanes Bowl & Bistro reinvents bowling night — ten ten-pin lanes with lane-side wait service, comfy seating, plus bocce, cornhole, and a seasonal outdoor bar. The upscale-casual bistro and full bar keep plates and pints coming, while trivia, music bingo, and live music fill the calendar. Book birthday parties, corporate events, and adult packages. An uncommon bowling experience in the heart of Mashpee.

9 Greene Street, Mashpee, MA 02649

The Picnic Box

The Picnic Box

Restaurant / Food & DrinkMashpee

Open daily 6am to 2pm in Mashpee, The Picnic Box is a local-all-the-way breakfast and lunch spot turning out some of the Cape's most raved-about morning plates. Dig into a classic lobster roll, golden fish and chips, hearty sandwiches, and homemade-style home fries served by friendly faces who treat regulars like family. Casual, consistent, and genuinely local, this Mashpee kitchen is where breakfast lovers keep coming back.

518 Falmouth Road, Mashpee, MA 02649

The Seal Pub & Cafe

The Seal Pub & Cafe

Restaurant / Food & DrinkHarwich

Billed as the friendliest pub and cafe on Cape Cod, The Seal in Harwich Center pours from 6am breakfast sandwiches straight through to 1am, anchored by famous fish and chips and golden-fried shrimp, scallops, calamari, and clam fritters. Add hearty chicken nachos, clam chowder, French onion soup, and expertly mixed dirty martinis, then finish with house carrot cake or cheesecake. Comfort food and craft cocktails in the heart of Harwich.

703 Main St, Harwich, MA 02645, USA

The Speedwell Tavern

The Speedwell Tavern

Restaurant / Food & DrinkPlymouth

At 47 Main Street in Plymouth, The Speedwell Tavern is comfort food done right, served laid-back and unpretentious. Sink into the South Shore's best wings, Certified Angus smash burgers, steak tips, and chili-loaded house-chip nachos. The craft beer list runs deep with local brews, the cocktails are honest, and live music plus game-day energy fill the room. This Plymouth bar and grill pours craft beer and good times in equal measure.

47 Main St, Plymouth, MA 02360

The Tasty

The Tasty

Restaurant / Food & DrinkPlymouth

The Tasty is an upscale-casual New American restaurant in the center of historic Plymouth, earning a loyal following for creative seasonal dishes and a warm, neighborhood-bistro feel. Dishes are ingredient-driven and locally sourced where possible, making this a standout option in a town better known for tourist traps. Reservations are recommended, especially on weekends.

42 Court St, Plymouth, MA 02360

The Tavern on the Green

The Tavern on the Green

Restaurant / Food & DrinkMarstons Mills

The Tavern on the Green sits at the Olde Barnstable Fairgrounds Golf Course in Marstons Mills, offering a casual dining experience with scenic views of the fairways. Serving breakfast and lunch daily, it's a welcoming spot for golfers and non-golfers alike — a relaxed Cape Cod tavern with local character and a comfortable atmosphere. The full bar and outdoor seating make it a pleasant stop any time of day.

1460 MA-149, Marstons Mills, MA 02648

Tigerhawk Sandwich Co.

Tigerhawk Sandwich Co.

Restaurant / Food & DrinkOak Bluffs

You'll find bold, chef-driven sandwiches unlike anything else on Martha's Vineyard at Tigerhawk Sandwich Co., Oak Bluffs' most exciting spot for globally inspired flavors. The menu is built around scratch-made sauces, high-quality ingredients, and inventive combinations — think Korean short rib with gochujang mayo and kimchi, local oyster po'boys, fried chicken hoisin, and porchetta with caper aioli and chimichurri. Everything is crafted fast without cutting corners, making it a favorite for lunch, dinner, and late-night bites. The approachable, counter-service vibe fits perfectly into the Circuit Ave energy, and online ordering makes it easy to skip the line. Whether you're island-hopping for the day or settling in for the summer, Tigerhawk delivers the kind of serious sandwich obsession that earns devoted regulars and well-deserved word-of-mouth buzz across the Vineyard.

12 Circuit Ave, Oak Bluffs, MA 02557

Tomatillos Southwestern Grill & Tequila Bar

Tomatillos Southwestern Grill & Tequila Bar

Restaurant / Food & DrinkSandwich

Spice up Sandwich at Tomatillos Southwestern Grill & Tequila Bar on Cotuit Road, where sizzling fajitas, shrimp tacos, and a knockout shrimp-and-lobster quesadilla meet an ocean-deep tequila selection. Sip a hand-shaken margarita, cap the night with fried ice cream, and ride the buzz of Taco Tuesdays, musical bingo, trivia, and weekend live music. Bold Southwestern flavor and Cape Cod nightlife collide in one lively, margarita-soaked Sandwich destination.

331 Cotuit Rd, Sandwich, MA 02563

Tomatoes Italian Grille & Bar

Tomatoes Italian Grille & Bar

Restaurant / Food & DrinkSandwich

Old-school Italian meets modern Italian-American at this Sandwich favorite on Route 130, where Sicilian country cooking and Northern Italian traditions share one generous, fresh-made menu. Expect heaping plates built from healthful ingredients, a welcoming bar, and dishes that satisfy both classic and adventurous appetites. With reservations, take-out, and delivery available, this Sandwich Italian grille and bar serves authentic Cape Cod dining the whole table can savor.

280 Route 130, Sandwich, MA 02563

Two Brothers Pizza and Mexican

Two Brothers Pizza and Mexican

Restaurant / Food & DrinkSandwich

Two cultures, one kitchen: Two Brothers Pizza & Mexican folds Greek-style pan pizza on dough made fresh every morning together with sizzling tacos and burritos at 331 Cotuit Road in Sandwich. Their family's secret sauce and three-cheese blend crown calzones baked golden, while hot pastrami and steak-and-cheese subs ride bakery-fresh rolls. For pizza, Mexican food, and overstuffed sandwiches in Sandwich, these brothers deliver two appetites' worth on every plate.

331 Cotuit Road, Sandwich, MA 02563

Uva Wine Bar

Uva Wine Bar

Restaurant / Food & DrinkMashpee

Pour your own discovery at Uva Wine Bar, Massachusetts' only self-serve wine bar, tucked into Mashpee Commons on Market Street. Sample fifty wines from across the globe in 2, 4, or 6-ounce pours, add draught beer, and pair flatbread pizzas, charcuterie, and cheese boards. With craft nights spotlighting local artisans and a retail wine boutique, this Mashpee tasting room makes wine exploration as easy and fun as it is welcoming.

4 Market St Mashpee MA 02649

Vineyard's Best Ice Cream & Coffee

Vineyard's Best Ice Cream & Coffee

Restaurant / Food & DrinkOak Bluffs

You'll find the kind of unpretentious island charm you didn't know you were looking for at Vineyard's Best Ice Cream & Coffee — a small, cash-only spot near the Oak Bluffs ferry terminal with a covered wraparound porch made for lingering. They scoop Richardson's Home Made Ice Cream (crafted in Middleton, MA), serve Seattle's Best Coffee, and knock out breakfast with MV Bagel Authority bagels, breakfast sandwiches, smoothies, and frappes. It's the perfect stop before or after the ferry — low-key, welcoming, and exactly the kind of place that becomes a morning ritual by the second day of your trip. Grab a seat on the porch, watch the Oak Bluffs foot traffic roll by, and enjoy a breakfast sandwich or a scoop without any fuss. Cash only, ATM on site.

12 Kennebec Ave, Oak Bluffs, MA 02557

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