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Little Rossa Pizzeria & Espresso Bar

Little Rossa Pizzeria & Espresso Bar

Restaurant / Food & DrinkFalmouth

At 261 Main Street in Falmouth, the spot Cape Codders knew as Simply Divine has become Little Rossa, a pizzeria and espresso bar pairing New York-style pies with pulled shots. Slide into one of the bistro chairs under the blue-striped umbrellas out front for a slice and a cortado, or settle in for dinner served till 10 on weekends. For anyone who wants a real New York slice and a proper espresso on the same Main Street stroll.

261 Main St, Falmouth, MA 02540

Lobster Pot

Lobster Pot

Restaurant / Food & DrinkProvincetown

Follow the famous neon lobster sign on Commercial Street and you've found the Lobster Pot, a Provincetown tradition serving fresh seafood and sweeping harbor views to guests from around the world. Generations have come for warm lobster rolls with drawn butter, panko-parmesan baked cod, Portuguese specialties, and chowder done the Cape Cod way. With outstanding hospitality and a front-row seat to Provincetown Harbor, this Provincetown seafood restaurant earns its waterfront legend daily.

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The Pinehills · Plymouth · Massachusetts

321 Commercial St, Provincetown, MA 02657

Local Grounds Coffee House & Cafe

Local Grounds Coffee House & Cafe

Coffee / Cafe / BakeryBourne

Set in a white farmhouse on Route 28A in Cataumet, this Bourne coffee house pours espresso and drip alongside bagels, breakfast sandwiches, acai bowls, smoothies, and lunch, with a dog-friendly patio and a carved wooden coffee-mug sculpture out front. The kitchen flags gluten-free options and leans toward fresh, made-to-order plates. For Upper Cape locals and cyclists who want a relaxed morning stop off the beaten path.

1370 MA-28A, Cataumet, MA 02534

Lucky's Corner Cafe

Lucky's Corner Cafe

Coffee / Cafe / BakeryEastham

Run by Nemo and Lucky, two hospitality friends who make every guest feel at home, this Eastham coffee shop on Brackett Road pours European-style espresso from local Snowy Owl roasters. Pair it with fresh juices, smoothies, additive-free homemade lemonade, and made-with-love bagels, donuts, and sandwiches. Genuinely fresh, genuinely healthy, and genuinely friendly, Lucky's Corner Cafe is the warm Cape Cod neighborhood spot Eastham reaches for every morning.

50 Brackett Road, Eastham, MA 02642

Mad Martha's Ice Cream

Mad Martha's Ice Cream

Restaurant / Food & DrinkTisbury (Vineyard Haven)

You'll taste island history at Mad Martha's Ice Cream, a Martha's Vineyard institution since 1971 — famously launched out of the back of an ambulance sedan by a farm girl who accidentally froze her cream supply and turned the mishap into something magical. All ice cream is made fresh daily in-house, and you'll taste the difference in every scoop. The Vineyard Haven location on Union Street is their newest home, offering the same beloved flavors that locals and summer visitors have lined up for across generations. Don't miss the mint chocolate chip, black raspberry, or the inspired Back Door Donuts apple fritter collab. With locations also in Oak Bluffs and Edgartown, Mad Martha's is the quintessential Vineyard summer ritual — the kind of cone you plan your afternoon around.

24 Union St, Vineyard Haven, MA 02568

Maison Villatte

Maison Villatte

Coffee / Cafe / BakeryFalmouth

Maison Villatte is a French bakery and café on Falmouth's Main Street that has earned the top spot on TripAdvisor's Falmouth restaurant rankings. The pastries — croissants, tarts, and eclairs — are made the traditional French way, and the café also serves savory crepes, sandwiches, and excellent coffee.

267 Main St, Falmouth, MA 02540

Marc Anthony’s Pizzeria

Marc Anthony’s Pizzeria

Restaurant / Food & DrinkWareham

World-famous pizza, hot and ready, delivered every day, all day, all year round to Wareham and Onset. Marc Anthony's Pizzeria builds its reputation on classic favorites done right: bubbling cheese pies, hearty Italian-American lunch and dinner plates, and dependable takeout that neighbors set their clocks by. Casual, generous, and family-rooted alongside its sister kitchens, this is the go-to Wareham pizzeria for pizza delivery that never clocks out.

190 Onset Ave, Onset, MA 02558

Marshland 3A

Marshland 3A

Restaurant / Food & DrinkPlymouth

Anchoring the Manomet stretch of Route 3A since 2012, Marshland 3A serves honest home-cooked breakfast, lunch, and dinner at prices that keep Plymouth regulars coming back. The menu roams from steak and burgers to fresh local seafood, while the summer deck and take-out window dish up fried seafood, fried dough, and ice cream. This easygoing Plymouth diner does reservations, take-out, and delivery.

986 State Rd, Plymouth, MA 02360

Marshland Too

Marshland Too

Restaurant / Food & DrinkSandwich

At 315 Cotuit Road, Marshland Too pairs the beloved Marshland home-cooked menu with Too's Tavern, a full-service sports bar and function room. Wake up to hearty breakfast, settle in for sandwiches, fresh seafood, and char-grilled steak, then linger over a late-night pub menu. This easygoing Sandwich gathering spot serves affordable scratch cooking morning through night, with game-day energy and a friendly local crowd.

315 Cotuit Rd, Sandwich, MA 02563

Martinis Bar and Grill

Martinis Bar and Grill

Restaurant / Food & DrinkPlymouth

Martinis Bar and Grill is a lively downtown Plymouth staple on Court Street, offering a menu that spans classic pub fare, fresh seafood, steaks, and pasta alongside an extensive list of handcrafted martinis. Live jazz on Tuesdays and live music Saturday nights make it a social hub as much as a dining destination. It's casual enough for a weeknight out and festive enough for a celebration.

50 Court St, Plymouth, MA 02360

Mezza Luna

Mezza Luna

Restaurant / Food & DrinkBuzzards Bay

Mezza Luna is a third-generation family-run Italian restaurant that has been a cornerstone of the Buzzards Bay dining scene for decades, serving classic Italian cuisine alongside fresh seafood, steaks, and nightly specials. The warm, welcoming atmosphere — complete with a full bar, lounge, and seasonal outdoor dining — makes it a go-to for everything from casual weeknight dinners to special occasion meals. Reservations are recommended on summer weekends.

253 Main St, Buzzards Bay, MA 02532

Midnight Mediterranean

Midnight Mediterranean

Restaurant / Food & DrinkOak Bluffs

You'll find bold, fire-kissed flavors at Midnight Mediterranean, a fast-casual walk-up window in the heart of Oak Bluffs that brings seven years of Mediterranean travel inspiration to every plate. Owner Jordan Wallace built the menu around flame-grilled kabobs, braised lamb gyros with herb salad and tzatziki, harissa chicken bowls, black bass branzino, and kale tabbouleh — all made from scratch with farm-to-table ingredients. Customize your bowl with feta, chili oil, pickled onion, confit garlic, or house tzatziki. The vibe is casual and grab-and-go — grab your bowl and head to the beach. Adjacent to Midnight Taco & Tequila Bar, this stretch of Circuit Avenue Extension has become one of the island's most exciting eating destinations.

6 Circuit Ave Ext, Oak Bluffs, MA 02557

Midnight Taco & Tequila Bar

Midnight Taco & Tequila Bar

Restaurant / Food & DrinkOak Bluffs

You'll find Southern California taco energy with a deep island soul at Midnight Taco & Tequila Bar, one of Oak Bluffs' most beloved spots since owner Jordan Wallace graduated from a food truck to a proper 50-seat restaurant in 2024. The menu is scratch-made using locally caught seafood from Oak Bluffs fishermen and produce from an in-house kitchen garden — think tacos, burritos, ceviche, and rotating daily specials that change with what's fresh. The tequila bar is the real draw on a warm evening, and the vibrant space frequently hosts live music and community events late into the weekend nights (open until 1am Friday–Saturday). Whether you're grabbing a quick bite or settling in for the full experience, Midnight Taco delivers the kind of good-time energy that keeps people coming back all summer.

7 Circuit Ave Ext, Oak Bluffs, MA 02557

Mocha Mott's

Mocha Mott's

Coffee / Cafe / BakeryOak Bluffs

You'll feel the heartbeat of Oak Bluffs at Mocha Mott's, the beloved community coffee shop that has anchored Circuit Avenue since 1994. Owner Meredith Aldrich and her team serve organic fair trade coffee and espresso drinks alongside homemade baked goods, Cape Cod bagels, soups, and daily specials — with no upcharge for non-dairy milk, ever. Gluten-free options are always on hand, and they even stock MV Barkery dog bones for your four-legged travel companion. The vibe is fast-paced, friendly, and genuinely local — a place where regulars and first-timers mix effortlessly over a perfectly pulled shot. Open mid-April through December, 6am–5pm daily. Their stickers have been spotted in all corners of the world, which tells you everything you need to know about the loyalty this place inspires.

10 Circuit Ave, Oak Bluffs, MA 02557

Nana's Caffè Italiano

Nana's Caffè Italiano

Restaurant / Food & DrinkSandwich

Step into Nana's Caffè Italiano and the braided sesame bread, premium Italian meats, and oil-and-vinegar layering tell you this Sandwich Italian cafe takes tradition seriously. Family-run on Cotuit Road, it pours rich Lavazza espresso, plates Modern Pastry favorites like pistachio crème cake, and builds cold hoagies, Sicilian pressed panini, and cutlet sangwiches. Add a salad and antipasto bar plus a rotating hot bar of meatballs and sausage with peppers for authentic Italian breakfast and lunch.

280 MA-130, Sandwich, MA 02563, USA

Nana's Ice Cream Parlor, And Candy Shop

Nana's Ice Cream Parlor, And Candy Shop

Restaurant / Food & DrinkWareham

For over thirty years this beloved Onset ice cream parlor has been scooping summer memories on Onset Avenue, churning out playful flavors like Graham Central Station and Fluffernutter alongside towering sundaes, soft serve, and refreshing Italian ice. Step next door into the vintage candy shop, where sour belts, dark chocolate coconut clusters, and old-fashioned sweets line the shelves. A cash-only, time-stands-still treat stop in Wareham worth crossing the bridge for.

196 Onset Ave, Onset, MA 02558

Nancy's Restaurant & Snack Bar

Nancy's Restaurant & Snack Bar

Restaurant / Food & DrinkOak Bluffs

You'll find Nancy's perched right on Oak Bluffs harbor — a beloved Martha's Vineyard institution operating since 1960. Walk up to the window and choose from a sprawling menu of classic New England seafood, a full sushi bar, and creative cocktails that keep regulars coming back all summer long. The menu carries a distinctive Middle Eastern influence that sets it apart from every other waterfront spot on the island. There are no reservations — it's walk-in only — which means the line can stretch, but the harborside setting makes the wait half the fun. Whether you're grabbing a lobster roll at the outdoor tables, sipping a frozen drink with a view of the boats, or sharing sushi at sunset, Nancy's delivers an experience that feels unmistakably like Martha's Vineyard at its most alive.

29 Lake Ave, Oak Bluffs, MA 02557

Osteria La Civetta

Osteria La Civetta

Restaurant / Food & DrinkFalmouth

Osteria La Civetta is a small, intimate Italian restaurant on Falmouth's Main Street helmed by husband-and-wife team Andrea and Sarah. Pasta is made fresh daily, the seafood is locally sourced, and the room has the understated warmth you'd expect from a proper osteria. Consistently one of the best dinner tables on the Cape.

133 Main St, Falmouth, MA 02540

Osterville Fish Market

Osterville Fish Market

Restaurant / Food & DrinkOsterville

Osterville's go-to seafood market and fried-seafood takeout — fresh fish and shellfish daily, live lobsters steamed at no charge, lobster rolls, New England clam chowder, and house-prepared specialties. Part of the family-run Osterville Fish.

2952 Falmouth Road, Osterville, MA 02655

Parrot Bar & Grill

Parrot Bar & Grill

Restaurant / Food & DrinkBourne

A tropical-themed neighborhood bar and grill on Route 28A in Cataumet, the Parrot pours from a full bar and turns out hearty pub plates: burgers, steak tips, sandwiches and garlic-parmesan chicken fingers. Between rounds there's musical bingo, trivia, karaoke and live bands that keep the room buzzing. Where Upper Cape locals land for an easygoing pint, comfort food and a little weeknight entertainment.

1356 Route 28A, Cataumet, MA 02534

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