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Aalia's Coffee
Tucked along a quiet stretch of Kennebec Avenue in Oak Bluffs, you'll find Aalia's Coffee — a beloved neighborhood spot that feels like a warm secret the island likes to keep. Inside, expect excellent espresso drinks and carefully sourced beans brewed with intention, alongside fresh baked goods that pair perfectly with the good music always humming in the background. The vibe is unhurried and welcoming, the kind of place where visitors slow down and locals linger. Whether you're fueling up before catching the ferry or settling in with a pastry after a morning walk through the Campground, Aalia's has a way of making every cup feel like a small act of hospitality. Seasonal hours apply — worth checking before you go.
16 Kennebec Ave, Oak Bluffs, MA 02557
Ben & Bill's Chocolate Emporium
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.