People in Cape May New Jersey, via benedek / iStock.com

6 Picturesque Small Towns in the Mid-Atlantic for a Weekend Retreat

When speaking of the Mid-Atlantic, what comes to mind? It's likely the beautiful beaches that come to mind, which, though cooler than their tropical counterparts, are less crowded and offer a serene environment. These beaches are surrounded by pristine nature, ideal for refreshing hikes, and feature warm sands during the peak of summer.

So, select a town that suits your preferences for a picture-perfect getaway, whether you're looking to relax, seek adventure, or indulge in seaside entertainment. Consider a chocolate-rich visit to Hershey, a journey filled with fascinating maritime trivia in St. Michaels (the town known for deceiving the British), or a shopping spree in tax-free Rehoboth Beach.

Cape May, New Jersey

Washington Street Mall at Cape May, New Jersey.
Washington Street Mall at Cape May, New Jersey.

Nestled in the southernmost part of the state and boasting breathtaking ocean views, this flourishing town has been attracting weekend visitors for centuries since its inception. As a coveted destination and the oldest seaside resort in the US, Cape May is a designated National Historic District, comprising over 600 preserved Victorian buildings.

Delighting visitors with its exceptional cuisine, fine wines, craft brews, and distilled spirits, Cape May is a national gem, making it an ideal weekend destination in the Mid-Atlantic for a scenic escape. Home to fun festivals and special year-round events, it's easy to catch Cape May at its most entertaining and vibrant. An up-close and personal look at the gingerbread-trimmed Victorian architecture is a must.

Victorian style houses in Cape May
Victorian style houses in Cape May

Don't miss the impeccably preserved Emlen Physick Estate from 1879, the trolley tour for a magical journey through the historic district, and the popular evening ghost tour. Washington Street Mall is a pedestrian-friendly hub of shopping activity, while the annual Cape May Restaurant Week features acclaimed participating eateries' delectable three-course selections. Home to dozens of Victorian B&Bs with authentic decor and modern amenities, your weekend will fly by in the natural beauty of this southernmost beach in the state. Wake up to the prospect of a morning stroll, jog, or bike ride along the scenic promenade with views of the sand, and search for Cape May Diamonds—polished quartz found along the shore—as a keepsake or a gift for a friend back home.

Hershey, Pennsylvania

Hersheypark, Hershey, Pennsylvania.
Hersheypark, Hershey, Pennsylvania. Image credit George Sheldon via Shutterstock

Hershey, a census-designated place rather than an officially incorporated town, is one of the most beloved small communities in the state. Owing its name to Milton Hershey, many honor the wealthy philanthropist who founded the Hershey Chocolate Company by visiting Hershey for a weekend of indulgence. With no other town like it in the nation, Hershey boasts Hershey Park theme park, near one of the very first chocolate factories, affectionately called Hershey's Chocolate World. It is a real chocolate affair for all-age chocoholics, with a walking tour through the processing areas for insights into the creation process of its heavenly goodies. Having offered tours for well over a century, today's visitors can enjoy an evolved experience with hands-on opportunities, allowing them to delve into making their own candy.

Hershey Park features rides and rollercoasters, including The Comet and Sidewinder, as well as a zoo and rides suitable for toddlers. The nearby Hershey Gardens from 1937 offer a lovely place with floral scents of roses and other flowers. Make it a weekend escape at Hotel Hershey, near the park and factory, with stunning bedrooms, recreational activities, in-room refrigerators, and coffee makers for that chocolate you couldn't help but stock up on. Imbued with the scent of cocoa, the town also holds military significance, having been the home of Dick Winters and his family after the war. His experience as the lead paratrooper with the Airborne Division during the liberation of Europe, starting from the Normandy Beaches, is documented in the ten-part HBO series, 'Band of Brothers.'

Lewes, Delaware

2nd Street in downtown Lewes, Delaware.
2nd Street in downtown Lewes, Delaware. By Tim Kiser, CC BY-SA 2.5, Wikimedia Commons

Lewes, once a Dutch settlement situated at the crossroads of Delaware Bay and the Atlantic Ocean, is now a picturesque town with 3,500 residents, hosting a vibrant atmosphere of cultural sights and attractions in postcard-perfect nature. No summertime visit to Lewes is complete without taking in the rays along its delightful beaches, picturesque trails, and seafood specialties. The colorful downtown area stays lively year-round with a conglomeration of Dutch-themed architecture and sites like the must-visit Zwaanendael Museum, housing state-wide early Dutch settlement artifacts, and a whole historic district with its beautifully preserved buildings from as early as the 17th century.

The beautiful town of Lewes, Delaware.
The beautiful town of Lewes, Delaware.

Brimming with boutiques offering a variety of keepsake crafts, visitors can enrich their wardrobes and find special items for their loved ones back home. Reenergize at Wheelhouse before meeting the sunset at one of the best historic lighthouses in Delaware Bay, the Harbor of Refuge Light or the Delaware Breakwater East End Light. From Cape Henlopen State Park to the Beach Plum Island Nature Preserve on the outskirts, explore Junction and Breakwater Trail just east. Spending a weeklong getaway along Delaware’s picturesque coast is easy, with local hospitality, rich history, and the sublime beach scene, particularly at Savannah Beach. Pilottown Marina, with its beautiful pier, is just a stroll away from the retail scene, including places like Bungalow on the 2nd.

Oyster Bay, New York

View of shops in Oyster Bay during the evening
View of shops in Oyster Bay during the evening. Editorial credit: Bing the Content Creator / Shutterstock.com

In 1653, Peter Wright, Samuel Mayo, and the Reverend William L. Leverich, along with the first settlers, landed at Oyster Bay Harbor. Raynham Hall, which is now a museum, served as the headquarters for the British Army during the American Revolution. Until the early 19th century, the town was predominantly rural before flourishing with the whaling industry. The introduction of the Long Island Rail Road in 1836 and the trolley car line at the beginning of the 20th century expanded movement, leading the town to welcome several industrial tycoons who built grand estates. From the patriotic waterfront offering relaxing views to the Theodore Roosevelt Memorial Park Beach, the quaint train station is conveniently located near the marina, adorned with proud white sails.

Oyster Bay, Teddy Roosevelt's favorite picturesque town in the southeastern Empire State, brims with sea views and historical buildings. Roosevelt's three-story mansion, “Sagamore Hill,” from 1880 at Cove Neck, was the summer White House for the first eight years of the new century. Behind this national historic site, bird lovers should not miss the Theodore Roosevelt Sanctuary, the nearby Trailside Museum, and the adjacent Young’s Memorial Cemetery with Roosevelt’s grave. Comprising over 30 incorporated villages like Massapequa Park and Oyster Bay Cove, visitors can explore in the presidential footsteps under the special blend of seaside ambiance and rural vibes. After dinner at the top local Wild Honey, head for a sunset drink at Cooper Bluff, a waterfront bar.

Rehoboth Beach, Delaware

Boardwalk at Rehoboth Beach in Delaware.
Boardwalk at Rehoboth Beach in Delaware. Image credit Ritu Manoj Jethani via Shutterstock.com

This quaint beach town on the Delaware Shores provides visitors with 30 miles of pristine coastline, featuring numerous waterfront parks ideal for kayaking, nature cruises, ferry rides, walking trails, surfing, boarding, sailing, and beachcombing. The Rehoboth Beach & Dewey Beach Resort Area boasts an award-winning boardwalk for strolls and access to great hotels, specialty stores, attractions, and attractive homes. Known as a tax-free shopping paradise with some of the finest restaurants, Rehoboth Beach attracts visitors to shop and dine among historical venues and live performing arts, enhancing its well-earned title of the 'Nation’s Summer Capital.'

Waterfront homes in Rehoboth Beach, Delaware.
Waterfront homes in Rehoboth Beach, Delaware. Image credit Khairil Azhar Junos via Shutterstock

Visitors can enjoy the outdoors right from their doorstep with beaches and state parks, while Highway One, also known as The Resort’s Gateway, provides access to a 'mile of style' at the famous Tanger Outlet Center, along with an abundance of bars and attractions. With so much ground to cover, there is no need to feel overwhelmed, but plan for spring or fall with events like sidewalk sales, a street market in May, Beach Goes Red, White, and Blue in September, and the Scarecrow Trail & Show through October, as well as the annual Sea Witch Festival. Visit any day to experience the small-town charm of Rehoboth Beach and its enchanting coastline, offering a peaceful retreat from the hustle and bustle of city life. A haven of coastal charm and lively entertainment, the pristine boardwalk captivates with its views of sandy beaches and the Atlantic, perfect for sunbathing and swimming.

St. Michaels, Maryland

St. Michaels, Maryland: Some of the shops and stores in St Michaels, MD along the town's main street.
St. Michaels, Maryland: Some of the shops and stores in St Michaels, MD along the town's main street. Editorial credit: George Sheldon / Shutterstock.com

Nestled along the Miles River in Talbot County, Maryland, Saint Michaels is a historic town and an iconic destination in the Mid-Atlantic region. Radiating aquatic allure from the picturesque Chesapeake Bay, this Eastern Shore gem has played a significant role in Maryland’s shipbuilding industry from its inception. Today, it reminisces about the bygone era with its beautiful waterfront and century-old buildings, where its fast schooner-style Baltimore clipper was once revolutionary for exports. Visiting a town with such a clever history as having “fooled the British” during the War of 1812 offers many enjoyable experiences.

Immersed in coastal nature and maritime tradition, Saint Michaels is now celebrated as the 'Heart and Soul of the Chesapeake.' With a flourishing arts scene, the town's recent seaside renaissance has revitalized the central town square while preserving the rich history of its architecture and historic buildings. Don't miss the Harbor Walk with its unique shops, lovely art galleries, and delicious seafood, and for nature lovers, the snaking St. Michaels Nature Trail offers aquamarine scenes with breathtaking bay views. The town's friendly population and bountiful bed-and-breakfasts are sure to dispel any city blues, especially during its yearly boat races and seafood festivals, while its opulent history wrapped in nautical grandeur will leave a soft spot in your heart, just like for many others.

In Conclusion

The Mid-Atlantic, with its distinctive features and astonishing geography, offers charming hamlets whose beauty you might not realize exists until you visit. Its balmy ocean breezes, local traditions, and historical charm will capture your heart, complemented by vibrant arts, nautical adventures, and some of the finest seafood. There's something for everyone to dive into, whether it's the Atlantic, history, or a plethora of attractions, all set against the backdrop of nature's picture-perfect views, with many surprises along the way.

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