Oak Bluffs, Massachusetts

Ben & Bill's Chocolate Emporium

Casual Family

Ice Cream & Sweets

Step into Ben & Bill's Chocolate Emporium on Circuit Avenue and you'll understand immediately why visitors return every summer without fail. This legendary sweet shop is part candy store, part ice cream parlor, and entirely irresistible — handcrafting their own chocolates, fudge, and confections right on the island since the 1980s. Dozens of ice cream flavors line the case, from classic New England staples to inventive seasonal creations, and the homemade chocolate-dipped everything will test your willpower at every turn. The shop buzzes with energy all summer long, filling the air on Circuit Ave with the unmistakable scent of warm chocolate. It's a rite of passage for Martha's Vineyard visitors of all ages — grab a scoop, pick up a box of truffles for the ferry ride home, and savor every bite.

Big Dipper Ice Cream & Cafe

Breakfast & Brunch

Casual Family · Coffee & Bakery · Ice Cream & Sweets

Right on Lake Avenue, steps from the Oak Bluffs harbor and the iconic Flying Horses Carousel, you'll find Big Dipper Ice Cream & Cafe serving up scoops and smiles from early morning through late evening. This casual, beloved spot doubles as a cafe and ice cream shop — perfect for a post-beach treat, a lazy afternoon break, or even a sunrise coffee before the island wakes up. The rotating flavors lean into New England classics with enough variety to keep everyone in the group happy, and the waterfront setting makes even the simplest cone feel like a small summer luxury. Families, cyclists, and day-trippers all find their way here — it's the kind of stop that turns into a tradition the moment you discover it.

Biscuits

Breakfast & Brunch

Casual Family · Takeout

You'll want to arrive early at Biscuits — this Oak Bluffs institution has been drawing crowds for its hearty, unforgettable breakfast and lunch since 2002, and the loyal following speaks for itself. Located on Lake Avenue a short walk from the harbor, the menu is rooted in classic diner comfort with a distinctly New England soul. The cod cake benedict is the stuff of island legend — a brilliant mashup of brunch and coastal tradition, finished with Old Bay hollandaise that you'll be thinking about long after the ferry pulls away. Everything is made with care, portions are generous, and the warm, no-fuss atmosphere makes you feel right at home. Open daily 7am–3pm. Come hungry, linger over coffee, and don't skip the biscuits.

Eleven Circuit

Bar & Brewery

Breakfast & Brunch · Casual Family · Seafood & Clam Shack

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.

Jetty Beach House

Bar & Brewery

Date Night · On the Water · Seafood & Clam Shack

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.

Midnight Mediterranean

Casual Family

Takeout

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.

Midnight Taco & Tequila Bar

Bar & Brewery

Casual Family · Takeout

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.

Nancy's Restaurant & Snack Bar

Bar & Brewery

Casual Family · On the Water · Seafood & Clam Shack · Takeout

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.

Nomans

Bar & Brewery

Casual Family

Nomans is a relaxed restaurant and bar on Island Inn Road in Oak Bluffs, built around good food, its own house rum and plenty of room to hang out. Find a seat at the long wooden tables inside or out in the yard, then head in to order from a menu of salads, grain bowls and bites; there's live music, yard games and a raw bar trailer under a sail shade outside. Seating is first come, first served with no wait list or reservations, and leashed, well-behaved dogs are welcome. A small shop corner sells Nomans hats, apparel and beach provisions.

Sand Bar & Grille

Bar & Brewery

Casual Family · On the Water

You'll land at the Sand Bar & Grille and immediately understand why it's Oak Bluffs' go-to harbor hangout. Established in 2002, this beachside bar and restaurant sits right on the water just steps from the ferry landing, with soft sand underfoot and the open sky above as your only ceiling. The menu ranges from signature lobster rolls and fish tacos to juicy burgers, specialty salads, and a full kids' menu — plus a rotating lineup of frozen drinks, craft beers, and cocktails that make every visit feel like a vacation. The vibe is relaxed and sun-drenched, the perfect place to watch the boats drift in and out of Oak Bluffs harbor. Whether you're grabbing lunch between ferries or settling in for a long summer evening, the Sand Bar delivers.

The Black Dog Dockside Cafe

Breakfast & Brunch

Casual Family · Coffee & Bakery · Takeout

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.

Tigerhawk Sandwich Co.

Casual Family

Takeout

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.

Vineyard's Best Ice Cream & Coffee

Casual Family

Coffee & Bakery · Ice Cream & Sweets

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.