5 Walks in 5 Cities

 @eatsforyiju

@eatsforyiju

My favorite place is whichever sidewalk is beneath my feet because I am just constantly fascinated by walking and looking and learning. If I've already walked a street five times, then the next five times I walk it looking up, and I learn something about the cornices.

- Danny Meyer (Michelin-starred chef of Eleven Madison Park & Shake Shack)


The Best Food & Culture Walks in America’s Most-Walkable Cities

The best way to explore a city is to walk it. There is no better way to feel the heartbeat of a city than by wandering its streets. The buttery aroma of fresh baked breads, the ornate facades and commuters darting past them, the banter between locals, the warmth radiating from the pavement - the only way to truly absorb a city is by walking it.

Of course, not all cities are designed for the pedestrian in mind. The late 20th century was unkind to many a metropolis; urban sprawl, suburban exodus, subservience to automobiles, under-investment in infrastructure, and booms in crime all plagued the American city. Despite this, America’s downtowns are fighting back, building denser, more pedestrian-friendly neighborhoods. New York transformed Times Square from car thoroughfare to a pedestrian-only park. Boston spent over $24 billion to bury a highway in tunnels beneath downtown. City governments pour over Redfin’s annual Walk Score rankings to better accommodate proximity to grocery stores, restaurants, public transit, green spaces, and cycling paths.

In celebration of the American urban renaissance, check out the top 5 most walkable cities based on walkability and culture, and my favorite app-guided walks to explore the best of them one foot in front of the other.

 @Luca Bravo

@Luca Bravo

New York City

Strolling Bonafides

The Big Apple sets the standard for offering both the most to see and the most walkable city. New York benefits from a convergence of factors: high population density, a gluttony of art and museums, a history of immigrants shaping world class culinary and cultural institutions, a flat terrain, a ubiquitous subway system, and a grid of streets laid out centuries before the invention of the automobile. In New York, you are only ever a few blocks away from a new neighborhood with its own architecture, food, boutiques and style.

Best Sidewalks for a Stroll

If you want to see the most iconic architectural wonders in the country, eat at a beloved 100+ year old subterranean restaurant, and get the details on the feud to build the world’s tallest building, you should check out the self-guided Sidewalk walking tour, Skyscrapers, Art Deco & Bitter Rivalries: The Landmarks of Midtown East. Along the way, you’ll visit some of the most celebrated architectural spaces including the vaulted reading room in the New York Public Library, the Greek gods emblazoned on the facades of 30 Rock, and the storied oyster restaurant hidden below Grand Central.

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San Francisco

Strolling Bonafides

Don’t let the steep hills of San Francisco intimidate you; SF is a fantastic city with ample (mostly) flat neighborhoods worth exploring. Set within a 7 mile by 7 mile peninsula, The City by the Bay packs in a ton of cultural heritage, iconic architecture, vibrant street art and culinary plates - from Michelin-starred feasts to farm-to-table food trucks. San Francisco is perfect for youthful urbanites, counterculture revolutionaries, farm-to-table foodatarians, outdoorsy hikers, beach bros and cocktail sippers.

Best Sidewalks for a Stroll

Each San Francisco neighborhood has its own idiosyncrasies, spirit and food culture, but the common themes are evolution and transformation. Perhaps the most apparent example is in the Mission District where young tech upstarts live next door to multi-generational Hispanic families. Explore the ways the two cultures interact through the neighborhood’s food. Check out Sidewalk Tastes | The Mission: Cuban Empanadas, Creole Bites & Handcrafted Sweets. Tastes are all-inclusive app-delivered culinary walks. Along the Taste, you’ll sample craft lattes, up-and-coming chefs, and cultural icons.

 @robert_bicknell_photo

@robert_bicknell_photo

Boston

Strolling Bonafides

The City on the Hill has reigned as one of the most influential cities in the US since its founding in 1630. Few other places allow the opportunity to follow in the footsteps of patriots and intellects, presidents and mobsters, athletes and scientists. This town is made for walkers; Boston and Cambridge (just across the Charles River) top the list of US cities with the most pedestrian commuters due to the small size, green parkways and convenient subway system (known as “The T”). More importantly, there is plenty to explore: boutiques in Back Bay, clam chowder at Faneuil Hall, picture-perfect cobblestone streets, cannolis in the North End, art-heisted museums, Red Sox sluggers at Fenway Park.

Best Sidewalks for a Stroll

If you only have a day in Boston, this is the Sidewalk you need to go on: Best Day in Boston: Revolutionaries, Gardens & Italian Pastries. Start in Back Bay at the finish line for the Boston Marathon and stroll past the quaint shops along Newbury Street, smell the flowers in the Boston Public Garden, sample pastries in the Italian district in the North End before concluding at the Old North Church where Paul Revere began his fateful ride.

 @sarahragucci

@sarahragucci

Washington DC

Strolling Bonafides

Memorials to American heroes, preeminent (free!) museums, Federal seats of power, multicultural diversity, monumental Beaux-Arts architecture and espionage intrigue… the Capital of the Free World offers an overabundance of significance and gravitas. Conveniently, Washington DC’s architects designed the city for foot traffic. Buildings are height-restricted so the Washington Monument can tower above the city. The Mall, a grassy parkway connects DC’s main attractions and serves as a stage to showcase the Capitol Building, White House, Lincoln Memorial and other iconic structures. No other city in the world matches Washington DC’s timeless dignity and pomp.

Best Sidewalks for a Stroll

For a break from the museums and government offices downtown, head to the narrow Colonial-era streets, charming cobblestones, historic canal and hip eateries of Georgetown. The Insta-Worthy, Tastebud-Approved Walk Of Georgetown in the Sidewalk app leads you to a legendary ice cream shop, block of quaint Row Houses, artisanal doughnut bakery, romantic towpath along a canal, and ornately irresistible cupcakes. Walking is the perfect way to earn (or burn) those treats.

 @molasa7

@molasa7

Seattle

Strolling Bonafides

The Emerald City sits atop hills surrounded by the gentle Puget Sound, looming mountain ranges and green forests. Seattle is unique in its balance of cutting edge technology (top employers include Boeing, Microsoft and Amazon) and rugged environmentalism, and between its diehard Seahawks football fans and its grunge music followers. Seattle is immensely walkable due to its simple grid layout, outdoor artwork, pioneer-era charm and artisanal espresso shops ready to caffeinate your stroll. Don’t let the rumors of constant rain scare you; the locals spin a whale of a story to limit how many people fall in love with the town and move there.

Best Sidewalks for a Stroll

Pike Place Market ranks as one of the most influential culinary markets in the country. With help from Sidewalk, discover the must-see and must-sample eateries, and the stories behind them. Flying Fish, Cheese Curds & Black Garlic: The Local's Foodie Guide to Pike Place Market leads you to hometown treasures: mini-doughnuts, creamy Greek yogurt, ginger beer, Washington cherries, and even the original Starbucks cafe. And of course, you don’t want to miss fresh salmon hurled through the air at the fish stand. Whenever visiting Seattle, at least one meal should be a strolling feast through Pike Place Market.


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Jason Donahue, Co-Founder & CEO

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