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Cupcake Charlie's - Mashpee Commons

Cupcake Charlie's - Mashpee Commons

Coffee / Cafe / BakeryMashpee

Life is short, so eat a cupcake at Cupcake Charlie's in Mashpee, where an open-kitchen bakery turns out gourmet cupcakes, custom cakes, cake pops, jars, trifles, and push pops fresh every single day. Gluten-free and vegan options, plus ice cream, keep everyone happy, while custom orders, wedding desserts, corporate catering, and fundraising packages make this Mashpee cupcake shop the go-to for celebrations big and small.

10 Central Square Mashpee, MA 02649

Cupcake Charlie's — Plymouth Waterfront

Cupcake Charlie's — Plymouth Waterfront

Coffee / Cafe / BakeryPlymouth

Cupcake Charlie's waterfront Plymouth location sits right on Town Wharf, putting gourmet cupcakes and sweet treats steps from Plymouth Harbor's lobster boats and historic scenery. The menu spans fresh-baked cupcakes, cakes, cake cups, and more, all made with the same craft that has made this brand a South Shore staple. It's the perfect place to grab something sweet before or after exploring Plymouth's storied waterfront.

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The Pinehills · Plymouth · Massachusetts

6 Town Wharf, Unit 4, Plymouth, MA 02360

Cupcake Charlie's — Wareham Crossing

Cupcake Charlie's — Wareham Crossing

Coffee / Cafe / BakeryWareham

Cupcake Charlie's at Wareham Crossing is a gourmet cupcake shop and bakery that goes well beyond the basics — fresh-baked cupcakes, custom cakes, cake pops, whoopie pies, trifles, and premium soft-serve ice cream. With rotating flavors and creative combinations, it's a sweet stop that draws loyal fans from across the South Shore and Upper Cape. Whether you need a dozen for a party or just one for yourself, they deliver.

2421 Cranberry Hwy, Suite 414, Wareham, MA 02571

Eleven Circuit

Eleven Circuit

Restaurant / Food & DrinkOak Bluffs

Right in the heart of Circuit Avenue, Eleven Circuit is the kind of place that works at any hour — whether you're starting the morning with a relaxed breakfast, gathering for a late lunch on the town, or settling in for drinks as the evening gets going. Open daily from 9am to 1am, this restaurant and bar strikes a balance between neighborhood hangout and lively entertainment venue, drawing a mix of locals and visitors who come for the food and stay for the atmosphere. The menu spans breakfast, brunch, lunch, and dinner, giving you plenty of reasons to drop in more than once during your stay. Private events and live entertainment round out the experience. Think of it as Oak Bluffs' living room — spirited, welcoming, and always worth a visit.

11 Circuit Ave, Oak Bluffs, MA 02557

Fairway Restaurant & Pizzeria

Fairway Restaurant & Pizzeria

Restaurant / Food & DrinkEastham

Open year-round on Route 6 in North Eastham, this tavern and pizzeria stacks thin-crust pies like BBQ chicken-bacon-ranch beside hearty breakfasts, fresh pasta, and local seafood. Dig into beer-battered cod fish and chips, cod fish tacos with chipotle ranch, turkey pot pie under flaky puff pastry, or a Tavern Burger with a cocktail from the bar. Weekly specials, custom coffee drinks, and dinner that keeps Eastham locals coming back through every Cape Cod season.

4295 Route 6, North Eastham, MA 02642

Ghelfi's Candies of Cape Cod

Ghelfi's Candies of Cape Cod

Coffee / Cafe / BakeryFalmouth

Ghelfi's has been a Cape Cod candy institution for decades, renowned for their chocolate turtles, sea salt caramels, and house-made fudge. The Falmouth Main Street shop is the original location, and their chocolates are also available to ship online. If you have a sweet tooth, this is a mandatory stop.

228 Main St, Falmouth, MA 02540

Graziella's Artisan Pizza Co. — Pocasset

Graziella's Artisan Pizza Co. — Pocasset

Restaurant / Food & DrinkBourne

Hand-tossed in the brick oven and built the way real neighborhood pizza should be, Graziella's Artisan Pizza Co. brings New York-style pies to Falmouth with house-made mozzarella, roasted tomatoes, garlic and basil crowning the Margherita. Beyond the pizza counter you'll find calzones, char-broiled Angus burgers, specialty wraps, fish and chips, and New England clam chowder. A Falmouth pizza spot where the dough is fresh, the toppings are honest, and done right is the whole point.

375 Barlows Landing Rd, Pocasset, MA 02559

Hey Sailor

Hey Sailor

Restaurant / Food & DrinkMashpee

Hey Sailor is a women's apparel boutique at Mashpee Commons with a breezy, vintage nautical aesthetic that captures the spirit of Cape Cod living. The shop carries carefully curated clothing, footwear, and accessories in classic maritime palettes — navy, red, white, and stripes — alongside a selection of coastal home décor. It's a local, woman-owned favorite for outfitting yourself in effortless Cape Cod style.

24 North St, Mashpee Commons, Mashpee, MA 02649

Hole in One Bakery & Coffee Shop

Hole in One Bakery & Coffee Shop

Coffee / Cafe / BakeryEastham

Ranked #1 on the Lower Cape for hand-cut donuts, this Eastham bakery and coffee shop fires up the ovens at 6am daily, turning out 18 flavors of from-scratch donuts plus homemade muffins, stuffed croissants, cupcakes, biscotti, fresh bagels and bread. Pair a still-warm pastry with a gourmet latte, cappuccino, chai or fresh-brewed iced coffee. A Route 6 morning ritual where breakfast on Cape Cod starts sweet and unmistakably handmade.

4295 US-6 (Route 6), Eastham, MA 02642

Hole in One Yarmouth

Hole in One Yarmouth

Coffee / Cafe / BakeryWest Yarmouth

The West Yarmouth outpost of Cape Cod's iconic Hole in One — hand-cut donuts, homemade muffins, fresh-baked pastries, and locally roasted coffee made from scratch every day. A Route 28 takeout favorite.

582 Main Street (Route 28), West Yarmouth, MA 02673

Ice Cream & Candy Bazaar

Ice Cream & Candy Bazaar

Restaurant / Food & DrinkEdgartown

You'll find a sweet escape at Ice Cream & Candy Bazaar, a charming waterfront confectionery tucked along Edgartown harbor. Step inside and you're greeted by 32 flavors of freshly scooped ice cream, bins of penny candy, house-made fudge, rich chocolates, and old-fashioned licorice — the kind of place that turns a quick stop into a lingering afternoon. The shop carries a wonderfully unhurried, classic-island feel with wheelchair-accessible seating right near the water. It's the sort of spot locals swear by and visitors stumble onto with delight — a family-friendly, no-frills gem that earns its 4.7-star reputation one scoop at a time. Whether you're loading up on nostalgic penny candy or going all-in on a double scoop, the Candy Bazaar delivers pure, simple joy with every visit.

5 Dock St, Edgartown, MA 02539

Jack in the Beanstalk

Jack in the Beanstalk

Restaurant / Food & DrinkSandwich

A Forestdale fixture on Route 130 in Sandwich since 1978, Jack in the Beanstalk stacks deli sandwiches on premium meats and cheeses, ladles homemade soups and chowders daily, and stocks a flavorful salad bar alongside hand-picked seasonal produce and groceries. Pour a fresh coffee, grab the famous apple cider donuts, and let their catering and gourmet gift baskets do the heavy lifting. Shop local, eat well, leave the cooking to them.

286 Route 130, Forestdale (Sandwich), MA 02644

Jetty Beach House

Jetty Beach House

Restaurant / Food & DrinkOak Bluffs

You'll feel like you've arrived at your best friend's beach house the moment you walk into Jetty Beach House, Oak Bluffs' exciting new coastal dining destination opening Summer 2026. The concept runs on three distinct vibes throughout the day: Sun & Salt (11am–4pm) with a fresh local raw bar, lobster rolls, and crispy fish & chips; Golden Hour (4pm–9pm) with craft cocktails and elevated small plates; and Into the Night (9pm–11pm) with DJ energy and late-night bites. Signature dishes include lobster pasta, steak frites, and the house Jetty Spritz. The atmosphere is casual, social, and beach-forward — the kind of place where you lose track of time in the best possible way. Open daily 11am–11pm.

8 Circuit Ave Ext, Oak Bluffs, MA 02557

John's Foot Long

John's Foot Long

Restaurant / Food & DrinkProvincetown

Since 1961, John's Foot Long has worked the same Lopes Square corner at 309 Commercial Street, slinging generous hot dogs and fried seafood to townies and day-trippers alike. The fried clams and scallops come out crisp and fresh, and the cheerful yellow-and-green stand is easy to spot on your way off the wharf. Best for anyone who wants an honest, quick Provincetown lunch eaten standing up, no reservation and no fuss.

309 Commercial St, Provincetown, MA 02657

Krua Khun Rose Thai Cuisine

Krua Khun Rose Thai Cuisine

Restaurant / Food & DrinkSandwich

Krua Khun Rose brings the real flavors of Thailand to Sandwich, building authentic recipes carried straight from home into intricate, original dishes plated with care. Spice levels flex from gentle to fiery, so every order suits your palate. This takeout-only kitchen on Cotuit Road keeps the focus squarely on culinary excellence, making it Sandwich's go-to for authentic Thai cuisine, traditional curries, and freshly prepared takeout done right.

289 Cotuit Road Sandwich, MA 02563

Lambert’s Farm Market

Lambert’s Farm Market

Restaurant / Food & DrinkSandwich

At 271 Cotuit Road in Sandwich, Lambert's Farm Market layers a full grocery, deli, butcher and bakery under one welcoming roof. Famous award-winning sandwiches, an on-premises butcher cutting quality meats, homemade decadent desserts, house cheese spreads, fresh produce and flowers, plus wine, champagne and prosecco for easy entertaining. Grab breakfast bagels or weekday lunch specials, order catering and party platters, then relax upstairs in the café. Sandwich's homemade-everything farm market.

271 Cotuit Rd, Sandwich, MA 02563, USA

Lazy Sundaes Ice Cream

Lazy Sundaes Ice Cream

Restaurant / Food & DrinkBourne

Scooping award-winning Richardson's Dairy ice cream, Best of Boston since the 1950s, Lazy Sundaes at Cataumet Crossing in Bourne stacks 55-plus flavors high: Maine Black Bear, Cape Cod Cranberry, Death by Chocolate, Coffee Heath. Add homemade waffle cones, thick shakes, sundaes, floats, and smoothies, plus vegan, sugar-free, sorbet, and Italian ice. A genuine Cape Cod ice cream destination near North Falmouth, built for warm-weather family fun.

1370 MA-28A, Cataumet, MA 02534, USA

Leo's Restaurant

Leo's Restaurant

Restaurant / Food & DrinkBuzzards Bay

Leo's is the quintessential Buzzards Bay breakfast spot — a no-fuss diner on Main Street that draws a loyal crowd of locals, tradespeople, and canal fishermen starting well before sunrise. Expect classic diner staples done right: eggs any way you like, thick pancakes, and coffee that keeps coming. It's the kind of place where everybody seems to know everybody.

249 Main St, Buzzards Bay, MA 02532

Leyden Street Coffee

Leyden Street Coffee

Coffee / Cafe / BakeryPlymouth

Coffee people run this place. Leyden Street Coffee roasts its own beans, services espresso machines for cafes across the South Shore, and pulls cappuccinos in Plymouth that regulars drive out of their way for. Open weekday mornings on State Road, it pairs flavorful single-origin roasts with flaky chocolate croissants, hot breakfast sandwiches, and a laid-back, dog-friendly room. Grab a bag of fresh roast, a keychain, and the best cup in town.

709 State Rd, Plymouth, MA 02360 (Manomet)

Liam Maguire's Irish Pub

Liam Maguire's Irish Pub

Restaurant / Food & DrinkFalmouth

On Falmouth's historic Main Street since 1994, Liam Maguire's pours the genuine article: a dozen-plus beers on tap, a deep wine list, seasonal drinks, and Chef Dave Mutti's plates of shepherd's pie, fish and chips, nachos, and potato skins. Nights here mean live music and craic, from Danny Quinn and the Shennanigans to trivia and Liam himself behind the mic. This Falmouth Irish pub turns dinner into a session and strangers into regulars.

273 Main St, Falmouth, MA 02540

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