8 Prettiest Downtown Strips On The Atlantic Coast
There is nothing better than a small town by the sea.
Up and down the Atlantic coast, small towns are rife with lovingly manicured gardens, excellent local seafood restaurants, and storied pasts, with some of the swashbuckling nature. From Florida to Maine, these eight towns boast some of the most attention-grabbing downtown drags, made for a leisurely day exploring the nooks and crannies that make them so oh-so-lovable.
St. Augustine, Florida
While the nation’s oldest city offers several charming streets in the Old Town district, St. George Street is commonly thought to be St. Augustine's main thoroughfare. With colonial buildings, brightly colored flags, and secluded courtyards, the street is where you’ll find some of the best dining and shopping options, along with some must-see attractions that denote St. Augustine’s rich history.
On the north side of the street is the Old City Gates, used in the 1800s as a defense against attacks and is now a popular place for a photo. Further down, the Saint Photios National Shrine is an educational center dedicated to Greek ancestry and heritage—you will enjoy learning more about the Greek Orthodox pioneers who came to the New World in 1768 and spend a contemplative moment in the gorgeous chapel adorned with Byzantine style paintings.
When it’s time for a snack as you meander down St. George Street, be sure to stop in at Whetstone Chocolates, a family-owned operation that’s been in business since 1967. And, to enjoy the best meal of the day—brunch—head to Prohibition Kitchen, a gastropub with speakeasy vibes and the most delicious shrimp and grits.
Beaufort, North Carolina
Located on North Carolina’s Crystal Coast, 85 miles of pristine Inner Banks beaches, Beaufort is full of maritime history and culinary adventures. Front Street is considered to be the main drag, and its boardwalk runs along the ocean, providing you with exceptional views while taking a leisurely stroll by the water.
Visit the North Carolina Maritime Museum to learn about Blackbeard’s connection to Beaufort and be regaled with stories of the pirate’s old stomping grounds and shipwreck off the coast of Fort Macon State Park.
Moreover, you’ll love Front Street for its range of restaurants in both cuisine and cost. Try Viet Street Eats for casual noodle dishes or Black Sheep for wood-fired pizzas made from scratch. For something a bit fancier, make a reservation at Moonrakers for a white-tableclothed, waterfront seafood meal.
If you’d like to get on the water, rent a kayak from Kitty Hawk Kites and walk down Front Street to Grayden Paul Park, a popular access point with free daytime storage so you can easily head back to the downtown area in between outings.
Lewes, Delaware
Lewes doesn’t like to brag, but it happily wears the crown as the “First Town in the First State.” You can find Lewes on the Delaware Bay, and its historic downtown area, commanded by the utterly quaint Second Street, will pull you right in.
Shoppers will love the mix of independent sellers housed inside the cedar-shingled storefronts. If you are a thrifting enthusiast, head to The Vintage Underground, a specialty shop where you can score used vinyl and vintage clothing. Or, try The Bungalow on 2nd for an eclectic parade of merchandise, underscoring its moniker as a lifestyle boutique.
The food scene in Lewes is not to be missed. Lewes Oyster House, otherwise known as a tavern by the sea, harkens back to a time when oysters were eaten as mere snacks, as readily available as popcorn or potato chips. If you are a fan of the mollusk, this moody restaurant is the place for you. If not, locals rave about the incredibly optimistic pizza place Half Full that welcomes guests for a happy hour drink or to grab a freshly-made pie to go. Agave is also wonderful for fresh margaritas and guacamole.
Just a block away from Second Street is CanalFront Park, a three-acre waterfront green space where you can relax and breathe in the ocean air.
Annapolis, Maryland
Established between the Severn River and Chesapeake Bay, Annapolis has earned the title of the “Sailing Capital of the World.” Much of this mid-sized city’s architecture dates back to colonial times, and its historic area is a great example of that.
The stretch of Main Street from Church Circle to City Dock is especially eye-catching and full of historical landmarks. Begin by gazing upon St. Anne’s Episcopal Church, the first church in Annapolis, founded in 1692 and designed in the Romanesque Revival style. On the other end of Main Street, it's vital to spend some time with the Kunte Kinte-Alex Haley Memorial, which tells the story of Kinte’s journey to Annapolis and subsequent enslavement and represents “the triumph of the human spirit over adversity.”
Main Street is also heavily populated with an array of amazing eateries of every type. You have to try the state’s famous Maryland blue crabs—when in Rome, obviously. The crab house Buddy’s Crabs & Ribs by the water is a fantastic place to start, but O’Brien’s Oyster Bar & Seafood Tavern mixes it up with a traditional crab soup and a hot crab dip.
End your tour of Main Street at City Dock, where the land meets the waters of the Chesapeake Bay. This is a great place to grab a sunny spot and watch as boats move in and out of Ego Alley, named for some of the more expensive yachts that saunter in and out of the narrow waterway.
Cape May, New Jersey
Often called “America’s Original Seaside Resort,” Cape May has long been a prime summertime destination for families on holiday.
While it’s known for its popular beaches, it also boasts a main street that takes a page straight from Pleasantville. Its official name is Washington Street, and it is a favorite destination for the over 11 million people who vacation in the seaside town each year.
Most prominently, the Washington Street Mall, a three-block span of the street, has 75 different shopping, dining, and entertainment options housed inside Victorian buildings. This pedestrian-friendly area is closed to vehicular traffic and has taken on the role of Cape May’s town square, hosting plant sales, sidewalk sales, and even the community Christmas parade. For a quintessential Cape May treat, hit up Fralinger’s Salt Water Taffy, a Cape May institution—the one pound box of taffy has remained the most popular souvenir for over 125 years!
When it’s time for a meal, a short walk will lead you to Maison Bleue Bistro, a classic French restaurant, and the Washington Inn and Wine Bar, an elegant space in the town’s historic district. And, located right behind the mall is the Cape May Rotary Park, a lush green space with plenty of park benches for people watching and a gazebo that becomes a stage for live music.
Southampton, New York
A village on Long Island, Southampton has long beckoned vacationers to its shores. The town’s tree-lined Main Street offers shade to its visitors who window shop along red-bricked sidewalks. There’s a broad selection of boutiques to browse—elegant home decor at Aerin, quirky hostess gifts at Hildreth’s, and fun fashion at alice + olivia.
With twinkle lights sparkling above the chic bistro tables, Main Street offers outdoor dining at its finest. This kind of magical ambience abounds at the highly-rated Le Charlot, 75 Main, and Dopo Argento, which are all located within steps of each other.
For a truly unique experience, visit the Pelletreau Silver Shop, a trade store that’s existed since 1686 and is now managed by the Southampton History Museum. There, you can book a lesson to learn how to make your own sterling silver jewelry with the shop’s resident artist and leave with a wearable piece of art.
Running perpendicular to Main Street is Jobs Lane, which will open up another round of dining and shopping options to you. However, a stop at the Southampton Arts Center is a must, with art exhibitions inside and a sculpture garden outside.
Nantucket, Massachusetts
Nantucket’s cobblestoned Main Street has two distinct segments—the peaceful, tree-lined Upper Main Street leads into Lower Main Street, the more bustling heart of downtown. Upper Main Street’s quiet residences show off a mix of architecture including the Greek Revival, Federal, and Georgian styles.
Lower Main Street is home to some of the best restaurants and shopping on the island. Opt for Lemon Press, an organic cafe in a cozy, exposed-brick setting and or, the Whale, a bistro with an enticing outdoor patio serving global fare. The latter’s allusion to ‘Moby Dick’ hints at Nantucket’s prominent history in the whaling industry, and you will love learning more at the Whaling Museum, just steps off Main Street on Broad. Be sure to visit Murray’s Toggery Shop, in business since 1945, to grab the whole family a pair of the iconic Nantucket Reds, shorts or pants in the island’s signature faded salmon-pink color.
Lower Main Street seamlessly leads right into the harborfront, and the thoroughfare ends where Straight Wharf begins. Strolling around this area provides you with spots for waterfront dining, meeting places for boat charters, and fantastic views of the Brant Point Lighthouse.
The Kennebunks, Maine
The Kennebunk River serves as a dividing line between Kennebunk and Kennebunkport, but interestingly, these two Maine resort towns share the same adorable downtown main street. With American flag bunting, bright pink petunias, and red brick sidewalks accenting the Federal and Colonial architecture, Western Avenue (which becomes Spring Street on the Kennebunkport side of the river) is a delightful way to spend a summer afternoon if the beach isn’t in the cards.
On the west side, you’ll love a coffee and breakfast crepe at Mornings in Paris, a French-inspired cafe popular with vacationers. Stationed right at the river is The Clam Shack, a casual, counter-service eatery serving delicious fried seafood baskets.
Moving east, you’ll find a number of specialty shops and boutiques like Minka, a thoughtfully curated shop filled with home decor, handmade blankets, artisan jewelry, and Daytrip Society, an all-things-Maine-inspired gift shop featuring clothing, jewelry, bags, and housewares that are perfect souvenirs to remember your stay in Vacationland.
Among the many dinner options, the Boathouse Restaurant located inside the Boathouse Waterfront Inn is a standout. You’ll know you’re in the right place when you see the “Love KPT” neon sign blazing over the harbor-try to grab a seat under a yellow umbrella on the restaurant’s spirited deck, complete with live music, cornhole, and creative craft cocktails.
Pretty Promenades on the Atlantic Coast
When it comes to Atlantic coastal towns, these eight are doubly blessed with stunning waterfronts and charming downtown strips that only add to the irresistible pull they have on vacationers around the world. From St. Augustine’s tucked-away courtyards to Nantucket’s cobblestoned streets to Kennebunkport’s touches of Americana, it’s easy to get lost in the charms of these downtowns. Pair that with unique shopping, important historical monuments, and cultural activities, you have a recipe for a day of fun on the prettiest promenades.
