For years, the Big Dig-- Boston's project to bury the Central Artery that separated much of the city from its harborfront-- was a national joke because of cost and schedule overruns, to the point that when cab drivers in other cities heard where you were from, they'd say, "Big Dig, huh?," and roll their eyes.
Today, though, the Rose F. Kennedy Greenway, the long-planned park that now occupies the site of the old highway, is proving the doubters wrong. Meandering one mile from Chinatown up to the North End, the Greenway is dotted with plantings, sculptures, fountains, pathways, and food trucks. Officially open since 2008, it has gained more amenities with each passing year, making it a true destination; a new addition this year is the carousel, located near Faneuil Hall. Boston finally has its connection to the harbor back, and it's making the most of it.
My favorite portion of the Greenway lies between South Station and Dewey Square, through the Financial District. This area is unusually high-density by Boston standards, and since it's occupied by businesses all but empties out over the weekend. Walking down the pleasant, populated Greenway next to cliffs of empty skyscrapers is a true Boston experience.
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Craving seafood in Boston? Head to Red’s Best at Boston Public Market for fresh clam chowder, lobster rolls, and local catch you’ll love!
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Sabina Mezcaleria is Boston’s first mezcal bar, offering smoky spirits, bold Mexican flavors, live salsa, and a vibrant Latin jazz brunch & tastings!
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Café Sauvage in Back Bay is a tropical-inspired spot blending French cuisine with African flavors. Enjoy their signature Roasted Chicken!
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Bricco Panetteria is a hidden bakery in Boston’s North End, offering artisan breads, pastries & a cozy, old-world charm. Try their Sfogliatelle!
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Greystone in Boston’s South End is a charming café with great coffee, fresh pastries, and a no-laptop vibe. Come here for a relaxed morning or lunch break!
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Parkside Bookshop in Boston’s South End is a cozy, pet-friendly gem with a thoughtfully curated selection, cozy reading nooks, and community events.
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Enjoy fresh pastries from Bakey any morning and take it to the Public Garden. Don’t miss their irresistible chocolate babka and burekas!
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Caffé Vittoria, Boston’s first Italian café since 1929, serves rich espresso, tiramisu, and affogato in a charming, old-world setting. A must-visit in the North End—cash only!
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Gypsy Place in Cambridge offers a bohemian vibe, fresh juices, vegan treats, and great coffee. Try the Azurite Bowl or Tiger’s Eye Truffles for a delicious energy boost!
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Cacao in Boston, run by a Dominican couple, offers rich hot chocolate, spicy cocoa, and delightful truffles — sweet haven for reading or writing.
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Escape the rush at Zuzu’s Petals in Cambridge’s Inman Square — a cozy, screen-free haven for fondue, wine, conversation, and homemade delights.
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Rouvalis Flowers in Beacon Hill charms every season with stunning blooms, dried arrangements, and gifts — perfect for adding beauty to any Boston day.
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129 Insider Tips from our local Spotters
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Escape the Crowd & Travel Slow 🐌
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✓ 129 Insider Tips