Nine Places in North America to Walk on Cobblestones

What is it about a cobblestoned street that immediately infuses a stroll through a historic city with infinite amounts of charm? Just the mere thought of treading upon crooked cobbles is enough to send a history buff into dreamland. You can't throw a stone in Europe without finding a piazza or boulevard covered in a jigsaw of flagstones, but here in North America's historic districts with cobblestoned streets are rarer gems to be treasured. We've put together our very own collection of North American cities with the most charming historic districts covered in cobblestones for your daydreaming pleasure.

1. Boston, Massachusetts
Gaslight streetlamps light the way down the narrow streets of Beacon Hill — one of Boston's most historic neighborhoods. Start at Charles/MGH train station and head south for a beautiful stroll through the labyrinth of Beacon Hill, and find Acorn Street, where window boxes line the cobblestoned street that was once home to the coachmen who worked for wealthy families on Mount Vernon and Chestnut Streets. For a few more cobblestones, follow the Boston Common to Faneuil Hall Marketplace, drive to the haunted city of Salem nearby or hop a quick flight to the historic island of Nantucket.

2. Savannah, Georgia
Climb down the steep, historic steps from Indian street to River Street, along the Savannah River. Two hundred years ago, cobbled River Street bustled with workers heading to the cotton warehouses, and sailors and pirates drank their grog and conversed about their exotic high seas adventures from Singapore to Bombay. The neighborhood was quarantined in 1818 and fell into ruin until urban planners renewed 80,000 square feet of abandoned warehouses into charming shops, restaurants and galleries.

3. Trinidad, Cuba
Trinidad is the second-oldest colonial city in Cuba and one of the best-preserved sugar-trade cities in the Caribbean. Its maze of dirt and cobbled streets are lined with brightly colored houses in hues of cornflower and sunflower, cantaloupe and key lime. Find your way to the cobbled Plaza Mayor, the center of the city, to admire this open-air museum of Spanish Colonial architecture, including the gold and seafoam tower of Convento de San Francisco.

4. Philadelphia, Pennsylvania
Head to the Old City District in Philadelphia, known as America's most historic square mile. Turn off Second or North Front Street onto the cobblestones of Elfreth's Alley, the oldest street in America, dating back to 1702. Admire the 32 houses built between 1728 and 1836 that once belonged to silversmiths, glassblowers and other tradesmen. While you're in the neighborhood, visit Independence National Historical Park and swing by Betsy Ross' 18th-century home!

5. Portland, Maine
Seabirds soar over craft breweries and gastropubs in converted warehouses along the waterfront of Portland, Maine in the Old Port District. Enjoy lunch al fresco at a café on the two cobbled blocks of Wharf Street. Shop and dine by day and try not to stumble on the cobblestones as you enjoy the bustling nightlife of this revitalized neighborhood.


6. San Miguel de Allende, Mexico
Jardín Allende, Jardín Principal, or simply "El Jardín" is the heart of San Miguel de Allende. It is in this UNESCO World Heritage garden square that you can feel the pulse of the city. Follow the cobblestoned streets of the compact centro historico to El Jardín to admire the "pink wedding cake" towers of La Parroquia de San Miguel Arcángel. Relax on a wrought iron bench in the shade of the manicured laurel trees, listen for the sound of mariachi on the breeze and watch as the city lives and breathes around El Jardín.

7. Baltimore
Fells Point: where hip meets historic. This waterfront community has been transformed through the decades from the 18th-century boarding houses, brothels and bars to trendy boutiques and seafood restaurants. Wander down the cobblestoned Thames Street that hugs the harbor, and learn about the German, Polish, Irish and Eastern European immigrants who have walked across those very same cobblestones over the past 250 years. Stop for oysters and climb aboard an urban pirate ship for a swashbuckling adventure.

8. Montréal, Canada
When it comes to the most charming and historic city in French Canada, it's a toss-up between Québec City and Montréal. (Why not learn about both?) By coin toss, we've selected Montréal. Explore the cobblestones of Old Town as you sit at a café along Rue St-Paul to enjoy some poutine, a crépe or les oeufs bénédictine. Listen to the locals chitchat in French, walk along the Old Port on the St. Lawrence River and enjoy the European atmosphere and charm without leaving the continent.

9. Charleston, South Carolina
Start your Saturday or Sunday in Charleston at Poogan's Porch for some fried green tomatoes, shrimp and grits, chicken and waffles or other Lowcountry cooking for brunch, and spend the afternoon ambling along Chalmer's Street and the seven other remaining cobblestoned streets of Charleston's Historic District. Make your way to the Greek Revival City Market to walk among locals and visitors alike as you shop for locally grown produce, handmade wares and Gullah sweetgrass baskets.

P.S.: Be sure to leave your heels behind and wear comfortable flats or sneakers to navigate! -JB