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The Most Picturesque Towns To Visit On The East Coast – Explore

North America is filled to the brim with stunning landscapes and rolling shorelines. From east to west, people in the United States are constantly reminded of the natural beauty and wonder that our planet offers up. Perhaps nowhere is this phenomenal beauty more evident than along the U.S. East Coast. Up and down the Atlantic corridor, small towns and booming urban sprawl have gobbled up the opulent sunrise that eastern shores and inland communities alike are able to bask in every day.

The East Coast is blessed with a meeting of Atlantic headwinds that make for generally mild temperatures and the graceful trickle of riverine waters that flow out to meet the ocean. These intertwined aquatic features have, over millennia, carved out protected bays and inlets, intercoastal waterways, rolling hillsides, and mountaintops that complete the region’s perfectly scenic vistas. Unfortunately for those who’ve caught the travel bug, this means that there’s an infinitely long list of fabulous towns to visit for that perfect view! History, geography, and the human spirit have collided over the last few centuries to produce a wealth of picturesque towns that dot this run of landscape. For the yearning adventurer, these are 18 of the most spectacular and picture-perfect towns in the eastern United States.

Provincetown, Massachusetts

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Provincetown is perhaps the quintessential small, picturesque town. It’s flung out 60 miles into the Atlantic Ocean on the very tip of Massachusetts’ Cape Cod and buffered on the interior edge by a long, sprawling beachhead. Provincetown Harbor supports a vibrant seafaring lifestyle and is the United States’ oldest continuous art colony. For over 100 years, “Provincetown has welcomed, nurtured, and inspired artists … not just to create, but to connect with the town and its people,” according to the Provincetown Art Association and Museum.

The people here are welcoming and relaxed, making this an excellent holiday destination for those in the LGBTQ community. Race Point Beach and Herring Cove Beach are both found a stone’s throw from the town itself and make for a wonderful day out amid the protected bay’s soft wake. For those looking to remain in the thick of the action, Provincetown’s Commercial Street can be found right in the center of town. It’s a highlight for anyone visiting this quasi-remote part of Massachusetts (although ferries and flights from Boston make it far less difficult to access). Commercial Street stretches three miles across the town and is filled to the brim with charming New England architecture, lobster joints, art galleries, and more.

Cape May, New Jersey

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Cape May can be found all the way down at the bottom of New Jersey’s coastal shore. Travel and Leisure calls it “one of the oldest vacation destinations in the country,” and Cape May named itself “America’s original seaside.” The Victorian-era building stylization (roughly 600 buildings, including the pristine Congress Hall, which has housed visitors since 1816) combined with the intercoastal harbors and string of inlets that worm their way back up the Jersey shoreline showcase the allure that has endured for generations in this small corner of the country.

This southernmost point in New Jersey is also just a two-and-a-half-hour drive from New York City, making it a great destination for a break if you’re a New Yorker. It’s also a great detour option for those visiting the Big Apple and its surrounding. Similarly, the town is fewer than 100 miles from Philadelphia (about an hour and a half drive). The community is also a great destination for visitors at virtually any time of year. In December, for instance, the town is dotted with Christmas lights and the shopping district reinvents itself as a festive winter wonderland experience.

St. Augustine, Florida

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In North Florida, St. Augustine is an easy destination to miss in favor of Jacksonville or the beaches of the Space Coast that stretch for miles down a little farther south. But St. Augustine is truly one of the most unique and historic settings in North America. It’s the oldest continually inhabited European town in the United States, having been founded in 1565 by Spanish explorers. Afterward, the town’s governorship passed back and forth between Spanish and English control, making for a truly unique cultural blend of influences in the cuisine, architecture, and people.

Datil peppers are a delicacy of the city and feature prominently in the town’s Minorcan cuisine and roots. No one knows for sure, but stories suggest the datil was either brought by the Minorcans or enslaved Africans. Or, it could have been simply found here. Regardless, it’s become a pepper that’s uniquely St. Augustinian.

The town sports a vibrant community and cultural architecture, including the Old St. Augustine Village block where homes from as early as 1790 still stand. But the town’s vista is dominated by a massive star fort. Built from coquina by the Spanish (to absorb cannonball impacts), Castillo de San Marcos is found right on the Matanzas River as the land opens up into the Atlantic beyond. Another crucial historical site here is Fort Mose, just north of the main town. This was the first free African settlement in America, an establishment older than the nation itself.

Seaside, Florida

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Another Florida location, Seaside is a truly marvelous town that’s not very well known. Yet, it really should be for anyone seeking out picturesque towns to soak in the ambiance and tranquility. This one caught the eye of Hollywood executives back in the late 1990s: Seaside is the real-world setting for the fictional Seahaven Island that’s home to Jim Carey’s Truman Burbank in “The Truman Show.” The town is a picture-perfect model of a place dominated by small, community avenues and white picket fences. The town centers on a prominent square (more of a rounded-out baseball diamond) that faces out into the Gulf of Mexico. The town radiates out in spokes from there, with small, coastal architecture and classic Americana overtones draped over the entirety of the town’s expanse.

The white, sandy beach stretches from one end of the town’s boundary to the other, as is often the case in communities along the Florida Panhandle. This is a virtually flawless example of what a picturesque town might exhibit.

[Featured image by paigeh via Wikimedia Commons | Cropped and scaled | CC BY-SA 2.5]

Montpelier, Vermont

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It might come as a surprise that a state’s capital city makes this list, but Montpelier isn’t your ordinary seat of government. The main chunk of Montpelier’s architecture can be found strewn along the north bank of the winding Winooski River, and the town itself supports a 2021 population of just 8,002. The city limits are somewhat expansive, but they stretch north into a significant wooded area rather than adding additional suburban sprawl to the community.

The community proudly blends the goings-on of a big city (like craft beer outlets and festivals) with the classic allure of small-town living. Montpelier is proudly the only state capital that doesn’t have a Mcdonald’s, Starbucks, or Walmart within its community. Similarly, hiking, skiing, and other outdoor adventure opportunities can be found just minutes from the center of town. According to Vermont Vacation, Montpelier “has been recognized as one of the 100 best small arts towns in the U.S.,” with the restored Vermont Statehouse standing as one of the oldest and best-kept in the country. The Statehouse’s golden dome stands out prominently from the surrounding infrastructure. But the town’s quaint aesthetic, draped in a collage of arboreal color that bursts into flames in the fall, makes for a spectacularly beautiful sight that simply shouldn’t be missed by discerning travelers.

Bar Harbor, Maine

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Bar Harbor is the largest town on Mount Desert Island. Even so, the community remains small, with a 2018 population count of just 5,535. The island is connected to the mainland by a single bridge from Trenton, Maine. When you make it across the Mount Desert narrows, you’ll be met immediately by a holiday RV campground that’s placed right up against the ocean. Upon reaching Bar Harbor, it’s difficult to not make a beeline for the lobster shacks and coastal views from the city’s harbor.

This remote northern reach of the country has been a summer home to many famous Americans, as well. The Vanderbilts, Rockefellers, Roosevelts, Morgans, and Fords are just some of the industry titans that made their way up to Bar Harbor to relax. While a fire in 1947 burned down much of the estate infrastructure that had been erected there, today celebrities like Martha Stewart and Susan Sarandon own summer homes in the town.

The sights of the town are unreal, to be sure. But the real beauty of Bar Harbor lies in its natural surroundings. South of the community, you’ll find Acadia National Park, and directly above the community a land bridge and hiking trail brings visitors to Bar Island. The tight community, combined with spectacular views into and around the harbor make this a necessary stop for anyone seeking beautiful, small-town America.

Asheville, North Carolina

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Asheville is far from a coastal town, but the community is nestled in the Blue Ridge Mountains and sandwiched between three national forests. Asheville is known for its booming music scene as well as a craft beer culture that has blossomed into a variety of great breweries.

Much of what Asheville has to offer visitors lies in the outdoor environment that permeates the town. Hiking in the area is second to none, as the town lies firmly within the Appalachian Trail’s southern reaches. The town’s center can be taken in from Pack Square Park — a green space that hosts local festivals and events, too. But perhaps one of the most impressive features of Asheville is the Biltmore Estate that lies just south of the main city blocks. This grand mansion was built for George Washington Vanderbilt II and is the largest privately owned dwelling in the country at 178,926 square feet. The estate is located on an absurd 8,000-acre landscape and has become a tourist destination complete with over 20 miles of hiking trails.

Frederick, Maryland

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Frederick lies adjacent to a sprawling forest and offers itself as a commuter town to both Baltimore and Washington D.C. (about an hour drive from both). This also makes it a fantastic option for those flying into the area who might be on the hunt for a hidden gem of a town. Running directly through the center of Frederick is Carroll Creek, producing a natural green space that cuts a swath right through the heart of the town. This means that no matter where you stay in Frederick, you’re likely a short stroll from this picturesque water feature. Similarly, while Frederick Municipal Forest and Gambrill State Park border the town on its western edge, the eastern reach of the community is dominated by the Monocacy River, adding yet another natural landscaping element to the community.

This unique location is also within close proximity to two Civil War Battlefields, housed within South Mountain State Park and Monocacy National Park. Visitors can also visit the National Museum of Civil War Medicine, rounding out a solid historical tour. To finish off a visit to Frederick, you can stop in at one of many distilleries and enjoy a drink.

Springfield, Massachusetts

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History is alive in Springfield. The town was founded by William Pynchon and his companions from Roxbury in 1636. Today, it’s known as the birthplace of James Naismith’s new game, basketball, and visitors can take in the game’s greatest moments at the Naismith Memorial Basketball Hall of Fame. In another vein, the town plays host to The Amazing World of Dr. Seuss Museum, as the esteemed author was from Springfield.

Situated along the Connecticut River, Springfield was established as a trading outpost located favorably between Canadian trading hubs to the north, and Boston and New York to the east and west, respectively. This positioning gave it an almost immediate significance in the world of colonial America. Later on, industrial power was drawn from the river, and the U.S. Armory was implanted into the DNA of Springfield in 1794. Springfield proper can be found on the eastern edge of Connecticut, and it has grown into a beautiful urban landscape that competes with even the most astonishing cityscapes along the East Coast. It’s truly a shame that Springfield has remained hidden in the shadow of bigger tourist destinations like Boston, Cape Cod, and Providence. Yet, the scenic town that supports a thriving art, culture, and historical scene can be driven to in just an hour and a half from Boston, making it eminently accessible to the keen explorer.

Ithaca, New York

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Cornell University dominates the landscape of Ithaca, New York. Located in the Finger Lakes region in the state’s west, Ithaca is sandwiched in the low-lying outfeed plain of Cayuga Lake and between two rising hills. Built up along a slender segment of the river’s waters, Ithaca is a sleepy town that’s surrounded by nature and fantastic hiking trails. Ithaca is consistently named one of the best places to live and work, and it’s complete with wineries, a thriving farmers market, and cultural community events that add to the picture-perfect scenery of the town itself and its vast, natural surroundings.

The university is a major draw for visitors. Cornell is an outstanding school (as you’ve likely heard many times if you’re a fan of “The Office”), and high school hopefuls often make up a large portion of explorers in the area. Cornell was founded in 1865, and its infrastructure reflects these historic underpinnings. Ithaca is a beautiful town that’s often overlooked to a traveler’s peril!

Savannah, Georgia

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Often found on travel lists among those looking to explore the United States, Savannah is one of the prettiest towns in the country. Savannah is the oldest city in Georgia, adding a layer of history and vintage charm into the mix. Savannah sits aside the Savannah River, right as it meets the Little Black River and the Georgia-South Carolina border.

Savannah is blanketed in aged oak trees, and one of the most iconic features of the town’s natural beauty is the Spanish moss that drapes down from their limbs. This feeds into the natural southern charm of the community’s green spaces, architecture, and more. Similarly, Savannah famously was spared the destructive fate of Atlanta and the 285-mile scar left by General Sherman during the Civil War. Instead, the Union general sent a telegraph offering the beautiful town to President Lincoln as a Christmas present. Some of the most photographed sites in Savannah are the Mercer House, Broughton Street, and The Olde Pink House.

Annapolis, Maryland

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Up the Chesapeake Bay and most of the way to Baltimore, you’ll find the small town of Annapolis. It’s home to the U.S. Naval Academy, an institution that sits prominently on the downtown area’s northern extent. Lower down, visitors will find a historic town that touts itself as “a museum without walls,” noting that it’s been named”the Athens of America,” and is one of the U.S.’ prettiest cities. Annapolis is also home to St. John’s College, an academic center that dates back to 1696. Across Annapolis, you’ll experience a unique maritime feel that permeates the community from the main harbor to residential neighborhoods. Annapolis celebrates this history with Wednesday night sailboat racing, and sports historical roots that date back centuries. This can be seen in the listless, carefree sprawl that flows out of the town center, as well as in the architecture of Annapolis itself.

Annapolis is about 45 minutes from Washington D.C., and 40 from Baltimore, making it a one-of-a-kind, coastal commuter town for either urban workplace. This also offers two quality points of access for a visitor flying in for a weekend adventure.

Roanoke, Virginia

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Roanoke is located in the western reach of Virginia, near Lynchburg, Charlottesville, and the historic Appomattox. The town is nestled in the Blue Ridge Mountains and finds itself within the Appalachian Trail. These mountainous features make it a phenomenally scenic community that’s bathed in natural beauty and a wealth of history. There are many places in the United States called “Roanoke” (seven, to be exact), but there’s only one that’s as beautiful a place as this.

Roanoke is known both as “Magic City” and “Star City,” and the names are fitting. Roanoke is home to 70 parks that encompass more than 14,000 acres and 100 miles of trails. It’s been named one of the top mountain biking spots in the world and is rounded out by beautiful architecture and a plethora of indoor and outdoor activities. The city supports a vibrant arts and entertainment industry, adding to the allure of this western gem in Virginia’s unspoiled natural atmosphere.

Portsmouth, New Hampshire

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Portsmouth is a coastal New England town much like Providence (Rhode Island) or New Haven (Connecticut). But this community is oozing with a unique small-town charm that many others simply can’t compete with. Portsmouth is shaped geographically by the calming influence of Great Bay to its east and the outflowing Piscataqua River above, rather than lying directly against the Atlantic’s more aggressive swell. Portsmouth can be found roughly an hour to either side of Portland, Maine, and Boston, Massachusetts, to the north and south, respectively.

Portsmouth was home to John Paul Jones, the Scottish-American naval hero, and William Whipple, one of the men who signed the Declaration of Independence. Both of their homes are now museums that visitors can venture through. Beyond these Revolutionary War-era residences, Portsmouth is bequeathed a variety of historic structures and an 18th-century garden. The retired U.S. Navy submarine USS Albacore is also moored here, allowing visitors to get a feel for what life is like beneath the surf. This seaside town is one of the most picturesque sights across the whole of America, not just its eastern extent.

Myrtle Beach, South Carolina

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Myrtle Beach is perhaps one of the largest towns on this list. Yet, it retains both the small-town charm that many of these destinations exude, as well as a vintage coastal vibe that’s difficult to match in terms of relaxation and enjoyment. It’s worth noting that Myrtle Beach plays host to a wealth of visitors every year, including a thriving shark population! 

The community is separated by a thin intercoastal waterway that shears its way along much of the South Carolina coastline. The area is also home to a number of excellent golf courses, meaning a few days wandering the beach isn’t the only activity you can busy yourself with while visiting this picturesque coastal carveout. Myrtle Beach’s Grand Stand area is the most popular part of the town for beachgoers and partiers alike. However, the entire stretch of beach (covering 60 miles of coastline up and down Horry County) makes for a picture-perfect vacation option. 

The high-rise beachside buildings scattered along Myrtle Beach offer a fantastic view of the rising Sun, and in the evening there are plenty of fresh seafood eats to dig into for a fabulous meal. Moreover, this beachside town is stocked full of inns and small beach hotels that can round out the perfect getaway that’s distinct from the typical city break. The town is always rocking with live music, and there are even a wealth of breweries and distilleries here to add an extra wrinkle to your plans.

Block Island, Rhode Island

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Out at the edge of Long Island and about 15 miles directly out into the Atlantic from the nearby ferry port of Point Judith, Block Island is a must-see. The northern segment of the island is separated almost entirely by Great Salt Pond, and this part of the island is home to Mansion and West Beaches as well as the Clay Head Nature Trail. Visitors can also take in the North Lighthouse and Settlers Rock up at the tip of the island. This community was founded in 1661 after Adriaen Block first visited in 1614. The island is technically comprised of a single town, called New Shoreham, and the community has grown up as a sleepy fishing village for hundreds of years since its establishment. In the late 19th century, mainlanders got wise to the beautiful scenery of the island, and its economy was transformed from primarily fishing to one of tourism. But the vintage architecture can still be seen to this day.

The town itself offers a plethora of boutique shops and restaurants, as well as a full calendar of events. The beachfront that runs around the island offers some of the best white, sandy beach real estate in the country, as well. All this comes together to create a stunning island town that sits at the intersection of nearly unparalleled history and natural beauty.

New Haven, Connecticut

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New Haven proclaims itself to be the “cultural capital of Connecticut.” It’s brimming with art, great eats, and all the trappings of a small, coastal community set down in the heart of New England. The town is penned in by a combination of rolling mountainous terrain to the north and the Long Island Sound beneath. To its east and west, the town is sandwiched between the West River and the Quinnipiac and Mill Rivers. These features add to the quiet and calming nature of the coastal community that isn’t short of beautiful views both into the sea and up toward the rising landscape beyond. Like a number of other picturesque American locales, New Haven is a college town that’s home to the prestigious Yale University.

Visitors can expect a full playbill of show options at the Shubert and Long Wharf Theaters, as well as some fantastic eats throughout the town. New Haven is known as the “Elm City” because residents launched the first public tree planting program in the United States (upon which, a significant volume of elm trees were added to the community). The town is also filled with stunning 19th and 20th-century architecture to match the ancient trees around the community.

Ocala, Florida

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Ocala can be found smack dab in the middle of Florida. This might not make it sound like an appealing vacation destination; however, you’d be wrong to discount Ocala’s natural beauty. Ocala is the horse capital of the world, with 1,200 thoroughbred horse farms scattered around the community. Ocala’s horses have won the Kentucky Derby six times and the Breeder’s Cup 20. The area has produced 45 national champions and six Horses of the Year.

Ocala isn’t just home to equestrian sport, though. The National Historic Landmark Fort King can be found in Ocala (a wooden fort originally built in 1827), and the Appleton Museum of Art round out the versatile happenings in this central Florida town. Ocala is also home to Rainbow Springs and Silver Springs State Parks, adding a vast, unscathed wilderness to the scenic allure of the town. Moreover, Ocala is roughly an hour and a half from the sprawling Orlando Disney World complex, making it a convenient stopover for those heading to Florida to see the Mouse.