The Most Charming Cobblestone Streets In America That Will Take You Back In Time

There's something extra magical about walking down a cobblestone street. Transporting you back in time with their authenticity and old-timey feel, cobblestones are sure to up the allure of any destination. Despite their beauty and durability, they've sadly gone out of fashion over the decades, with most cities turning to more practical and affordable materials, like concrete, instead. However, there are luckily a number of cobblestone streets, and even neighborhoods, that still remain across the country, retaining much of their historic architecture and overall charm.

Although cobblestones are frequently associated with Europe, there are a number of spots across the United States that have employed the historic material as well. Since there are a fair number of spots throughout the country that still have historic cobblestones, we have narrowed down some of the best that are sure to take you back in time. Just remember to pack some comfortable walking shoes — cobblestone streets are notoriously bumpy and uneven.

Although Philadelphia, Pennsylvania is one of America's most underrated cities, has a number of cobblestone streets, one of its most charming and all-around iconic is Elfreth's Alley. This National Historic Landmark has the distinct honor of being the oldest continuously-inhabited residential street, and although it has undergone a number of changes over the years (during the alley's earlier years, grocers, shoemakers, cabinet makers, tailors, and more operated out of their Elfreth Alley homes), it has retained much of its original charm, which visitors can see through its old-timey flower boxes and shutters, brick buildings, architecture style, and of course, the cobblestone street.

The alley is only a block long, but with over 30 homes all built between 1728 and 1836 — two of which now serve as a museum and a gift shop, open Fridays to Sundays — it's well worth a stop for a look into Philadelphia's history. If you visit during the first Saturday in December, or on Fete Day in June, current residents even offer visitors a peek into their private homes. "Very cool little preserved street in Philadelphia," said one past visitor on Tripadvisor. "It's really fun to be able to submerge yourself in the ambiance of the time!"

Savannah, Georgia is another city brimming with historic appeal, but one of its most notable historic areas is no doubt River Street. Its cobblestones actually uniquely come from around the world — they originally were used as ballast material on ships that arrived in Savannah. Stroll along the 200-year-old waterfront cobblestones and explore the many shops, restaurants, and art galleries. Be sure to also stop by River Street Market Place, an outdoor market similar to the open-air markets of the 1800s, for handmade jewelry. You'll often find that there are local events going on and live music — River Street is the place to be, especially around the holidays.

History buffs can also check out the number of interesting monuments throughout the area, while nature-lovers should head to Skidaway Island State Park, Savannah's best secret vacation spot. "Stroll along the quiet river, eat at one of the many restaurants, stop for ice cream, shop to your heart's content, enjoy the statues, feel immersed in history with sites of steamboats and cobblestones," said one Tripadvisor reviewer. "Come for an hour, spend the whole day."

For historic allure in the heart of Baltimore, Maryland, head to Fell's Point. Dating all the way back to 1763, and as Maryland's first National Historic District, it's a popular hub for nightlife. Among the neighborhood's many of cobblestone streets, the waterfront Thames Street is a highlight, with a number of restaurants, pubs, and more to explore.

The Horse You Came In On Saloon, which opened in 1775 and is the country's oldest continuously operating saloon, is rumored to have been the last place Edgar Allan Poe was seen before his death, while Rye of Baltimore is a popular speakeasy bar beloved for its stellar cocktails. Thames is also home to a number of great spots for live music, like the Admiral's Cup and Waterfront Hotel. From Thames, also be sure to make a stop at Broadway Pier for a beautiful view of the Baltimore Harbor. "This harbor is absolutely breathtaking and offers so many things to do," said a past visitor on Tripadvisor regarding Fell's Point. "There are amazing restaurants like Penny Black and Thamas [sic] Oyster House ... Make sure to take some time to visit!"

Wharf Street is a picturesque cobblestone alley tucked away in Portland, Maine's Old Port District that's sure to satisfy any craving for history and postcard-worthy destinations. While exploring the surrounding area — which is a "restaurant mecca," according to one Tripadvisor reviewer, especially for seafood lovers — be sure to stop over on Wharf, a pedestrian-only walkway filled with gorgeous 19th-century brick architecture. Wharf Street is well worth a visit at any time of day, as a popular hub for shopping and dining, as well as nightlife.

Especially considering that Portland is one of the most underrated food destinations in America, you won't want to skip grabbing a bite to eat in this area, either. Pay a visit to Bar of Chocolate for a cocktail and a dessert, and Street and Co. for Mediterranean-style seafood. There are a number of parks within a short walking distance when you're in need of some nature, and the Portland Waterfront Historic District is just minutes away as well. "We spent most of our time of the trip down in this area, specifically Wharf Street," said another Tripadvisor reviewer about the Old Port District. "There was not a single place that disappointed us!"

With at least 100 cobblestone streets throughout Seattle, Washington, including at the iconic Pike Place market, there is certainly no shortage of history in this West Coast city. Its best example, however, is at Pioneer Square. With ivy-covered, Romanesque Revival buildings, a thriving arts community, and of course, cobblestone streets, Pioneer Square is absolutely brimming with history and charm. Seattle's very first neighborhood, established in 1852, offers plenty to see and do, and the neighborhood is well worth at least a few hours of your time.

History lovers shouldn't skip a visit to Klondike Gold Rush National Historical Park on Second Avenue, or an underground tour (literally) for 1890s architecture and anecdotes about Seattle's early days. Shopping and dining spots are abundant, as well. "Pioneer Square is rarely mentioned as an attraction like Pike's Place Market and the Space Needle, but it is central to Seattle's history," said one Tripadvisor reviewer. "Seattle's history is a must see."

The island of Nantucket, Massachusetts is one of the best areas for history buffs and seekers of picturesque travel destinations. And while the region truly comes alive during peak summer season, Nantucket is more than worth visiting during the off-season as well, especially for those who prefer a more laid-back atmosphere. While there's much to love about Nantucket, one of its most unique elements are its cobblestone streets, which date all the way back to the 1830s, and remain today as a reminder of Nantucket's past as a vibrant trading center and the whaling capital of the world.

Among its most charming examples is Nantucket's Main Street. With gorgeous Greek Revival mansions adding a quaint feel and tranquil waterfront views, not to mention its distinct cobblestones, there are few places more picture-perfect. For a bite, stop by Or, The Whale, an American bistro with an outdoor patio, and be sure to head to Vis-A-Vis for some shopping.

The oldest cobblestone street in Virginia is none other than Captains Row in Alexandria, a scenic block of Prince Street named for Captain John Harper who built some of the area's homes in the late 1700s, many of which were inhabited by sea captains. Most of the stones come from the nearby Potomac River, although legend says that the cobblestones were brought from England and laid by imprisoned Hessians, German soldiers hired by the British during the Revolutionary War.

Over the decades, the block underwent many challenges, from fires to floods to disease. In the 1960s, however, the area was revived, breathing new life into it and making it into the beloved destination it is today. Nowadays, it is an undoubtedly appealing area worth a stop, especially when accompanied by a walk through the rest of Old Town, known as King Street, where plenty of restaurants and stores can be found. Just take it from one Tripadvisor reviewer: "The Captains Row is a must see when coming to the Old Town." 

When it comes to its diverse array of things to do and rich roots in American history, Boston, Massachusetts is easily one of the best cities in America, according to travel writer Rick Steves. So, it's no wonder why one of the country's most prominent examples of charming cobblestones is Acorn Street in Boston's Beacon Hill neighborhood. This picturesque street is said to be one of the most photographed in the U.S, all complimented by its red brick houses. Initially built in the 1820s, merchants and artisans called Acorn Street home. The street was named for the number of acorn trees that once bordered the historic area.

Past visitors say that the street is small, so don't expect to spend more than 10 minutes or so wandering through (and snapping a couple photos of your own). Nearby is the well-known Freedom Trail, which leads through a number of the city's historic sites, as well as Boston Common, the oldest public park in the United States. "Such a historic and beautiful little street that just draws you in like time stood still!" said one past visitor on Tripadvisor. "It's perfectly charming!"

Charleston, South Carolina has just eight remaining cobblestone streets, but one of its most photographed is Chalmers Street in the city's French Quarter. The street runs past Washington Square, which is home to the South Carolina Historical Society. And with an abundance of art galleries surrounding the area, particularly on nearby Broad Street, there's plenty of history and culture to explore here.

On Chalmers Street, stop at the Pink House, which dates all the way back to the late 1600s or early 1700s. Initially built as a tavern (and possibly a brothel), the Pink House, which is constructed with a coral-colored stone from India, is now an iconic fixture of Charleston. Those looking to learn about South Carolina's history should also pay a visit to the Old Slave Mart Museum on Chalmers. A reservation is required and adult admission is $8. Afterwards, head to nearby East Bay Street to take a look at the iconic Rainbow Row, where you can find a number of picture-perfect pastel-colored homes.

Benefit Street, a mid-18th century colonial road in Providence, Rhode Island, is practically a paradise for fans of history. While a large portion of this cobblestone street is made up of beautiful and historic residences, it is home to a couple of touristic gems, from the Providence Athenaeum, a gorgeous Greek Revival library dating back to 1838 and one of Rhode Island's oldest cultural institutions, to the Old State House, the center of colonial Rhode Island's political history and the site where the state officially declared its independence from England in 1776. Benefit Street is a "treasure trove of history," to use the words of one past visitor on Tripadvisor, who also recommends a visit at dusk when the streetlights come on. "A great stroll down history lane can be seen here."

It's also where you can find the impressive Nightingale-Brown House, which was built in 1792 and was the residence of five generations of the Brown family (of Brown University), until the home was donated to the university in 1985. From Benefit Street, you can easily visit a number of other historic destinations throughout the neighborhood, such as the John Brown House Museum, and cultural institutions like the Providence Art Club. "There are some hills to climb but the feeling of history, with cobblestone, old brick and restored homes was delightful," said a Tripadvisor reviewer.

While many of the country's most notorious cobblestone streets are sprinkled across the East Coast, the Midwest has some cobblestone gems of its own, and one of its best is no doubt located in Minneapolis, Minnesota. Some time spent in the Riverfront District is a must on any Minneapolis itinerary — and one of its highlights is the cobblestoned Main Street. Particularly in the St. Anthony Main area, which is the city's oldest pocket, there's plenty of historic character and charm to be found while sightseeing, dining, and enjoying views of the Mississippi River. There's plenty to explore on foot, or instead hop on a bike — this Midwest gem is America's most bikeable city, after all.

Along the popular entertainment and restaurant district, catch a movie at The Main Theater (it shows both independent films and new releases), or take a walk through the Historic Main Street Park. For an urban area, there's plenty of green space, and the nearby state park, Father Hennepin Bluff Park, is also a popular destination if you're looking for more hiking trails and wildlife. Definitely don't miss a walk around the St. Anthony Falls Historic District Area's Heritage Trail, a self-guided 2-mile loop, which offers views of the St. Anthony Falls — while some visitors say that it is perhaps not the most scenic waterfall you'll ever see, it is historically significant to the area and an interesting sight to behold. "This place is not advertised enough," said one Tripadvisor reviewer. "The views are stunning." For food, Aster Café on Main Street has a European-style patio which pairs perfectly with the city's historic charm and views.

New York is a history-rich, foodie paradise, and Stone Street, although just a block or so long, holds its weight. This pedestrian-only street in Manhattan's Financial District has been a nightlife destination since the 1600s. Not only was it New York's (at that time, New Amsterdam's) first paved street, but it notably was home to the city's first printing press, as well as a number of colonial-era breweries. Today, it is an utterly charming blend of old and new — although it is surrounded by quintessential New York City skyscrapers and underwent a period of disarray, by the late '90s, it became a protected NYC landmark and a designated historic district, leading to its restoration and revitalization.

Nowadays, tourists and locals alike can peruse the lively wall-to-wall restaurant and bar corridor, and attend the outdoor street festival that comes to Stone Street about five times a year. Among its vibrant food scene, visitors have their pick of Mexican cuisine, Cuban food, an Irish pub, Spanish tapas, an oyster bar, Italian food, and more. Whether you're looking to bar-hop or just enjoy some outdoor seating and take a few photos, Stone Street is a must. Manhattan's Stone Street is "like stepping onto a film set for a historical film," said one Tripadvisor reviewer. "I'm not sure how these buildings survived, but I'm glad they did!"

We have visited a number of these highly charming destinations, and used our personal experience to compile this list of best cobblestone streets in America. In addition, we used a fair amount of research to verify our claims and to round-out our recommendations. The sources we used included Tripadvisor reviews, travel blogs, travel publications, and destination-specific sites. We also made sure to include streets in a number of different states.