Discover the Charm of Small-Town Delaware

Steve Jennifer
Updated: May 16, 2024

Delaware, much like stepping into an old-time candy shop, presents a delightful array of choices that charm and invite. Brimming with small-town allure, natural beauty, and warm hospitality, America's first state offers idyllic beaches, unique dining experiences, and vibrant festivals rich in fresh seafood delights. Each town boasts its own slice of history, making every quick trip as enlightening as it is enjoyable.

01. Milford – Discover Craft Beer, Art, and Endless Festivals

Milford, a lively town known for its dynamic festivals and thriving craft beer scene, is a hotspot for those who enjoy the zest of life. Make the most of a Third Thursday Celebration, where local shops and eateries offer extended hours and special deals. Don’t miss the Riverwalk Farmers Market in October, and with a plethora of breweries nearby, you’re sure to find a favorite brew.

02. Lewes – Step into Delaware’s First Town

Start your adventure in Lewes, Delaware's oldest town, by visiting the quaint Zwaanendael Museum. Famous for its serene beaches and rich history, the view from Cape Henlopen State Park's tower is truly breathtaking. Immerse yourself in WWII history, then enjoy a leisurely walk along the canal, topping it off with delectable seafood at the renowned Harbour restaurant.

03. Smyrna – Where History Echoes in Every Corner

Smyrna, once a bustling shipping hub for goods traveling north until around 1850, stands along the historic King's Highway. Today, it boasts a population of about 12,000 residents. This town isn’t just a dot on the map—it's a treasure trove of history. With nearly 850 buildings in its historic district, many of which are listed on the National Register, Smyrna is a real blast from the past. Originally known as Duck Creek Cross Roads, this charming town also offers a rare treat: Lake Como, one of Delaware's few public swimming lakes.

04. Hockessin – Quaint and Utterly Enchanting

Just a stone's throw from Pennsylvania, Hockessin is home to historical sites like one of the first Quaker meeting houses and the first Roman Catholic Church in Delaware. Now, it also hosts the Hindu Temple of Delaware, reflecting the town’s cultural diversity. Relish the local produce and home-cooked meals at Lettie's Kitchen or grab a craft beer from Dew Point Brewing Company in nearby Yorklyn.

05. Rehoboth Beach – Dive into the Best of Seaside Living

Rehoboth Beach, dotted with summer homes, is a jewel on the Atlantic coast, drawing visitors with its stunning beauty and vibrant community events like the Sea Witch Festival. Whether the weather cooperates or not, the charm of Rehoboth Beach ensures a memorable visit filled with sand, surf, and fun.

06. Millsboro – Founded by Pioneers, Loved by Many

Founded by Virginian settlers seeking timber, Millsboro quickly grew around Elisha Peterson’s dam on the Indian River. Experience the town’s rich history and enjoy a picnic by the riverbank with tasty bites from Longneck Deli or Ada's Picnic, and soak in the tranquil atmosphere.

07. Delaware City – Come for the Waterfront, Stay for the Views

At Delaware City, the waterfront scene at Battery Park is where the action is. This vibrant area, with its annual festivals and proximity to historical sites, invites visitors to engage deeply with the town’s lively culture. Explore on foot, enjoy a ghost tour, or simply relax at the marina—Delaware City offers a picturesque escape.

08. Dover – Get Ready for Fun in Delaware's Capital

Experience the excitement of Delaware's capital, Dover. Test your luck at the casino, explore historic sites like the John Dickinson Plantation, or learn about vintage aircraft at the Air Mobility Command Museum. With its speedway and rich cultural offerings, Dover offers a blend of thrill and educational exploration.

09. Slaughter Beach – Memories of Summer Playgrounds

Slaughter Beach, originally a chic summer retreat for the elite, now serves as a quiet haven with a population just over 200. It's a must-visit for bird watchers and nature enthusiasts, particularly during the horseshoe crab migration season at the Milford Neck Wildlife Area. This area offers a glimpse into the raw beauty of nature and a peek into the town's glamorous past, making it a perfect spot for those seeking tranquility or a touch of the unusual.

10. Little Creek – A Hidden Gem in Delaware

@littlecreekcreations

Little Creek, now little more than a historical footnote, was once a bustling center for the Delaware Bay oyster industry. From its early days as a wharf between plantations to its incorporation in 1899, the town thrived until the 1930s. Today, visitors can immerse themselves in its past through 11 farm complexes, a unique octagonal schoolhouse, a Quaker meeting house, and a cemetery, all part of the Little Creek Hundred Rural Historic District.

11. Laurel – Wrapped in Natural Splendor

Laurel, once a key player in Southern Delaware's grain and lumber industry, now enchants visitors with its revitalized downtown and scenic waterfront along Broad Creek. History buffs will appreciate the unique "potato houses," while outdoor enthusiasts can explore the Loblolly Trail at nearby Trap Pond State Park, renowned for its stunning Bald Cypress trees. The Nature Center offers a deeper dive into the area's rich ecological diversity, making Laurel a haven for nature lovers.

12. Magnolia – Preserving Its Historic Borders

The small town of Magnolia, designed with a circular layout to symbolize brotherhood, has maintained its original quarter-mile diameter to this day. Despite its modest size and population of just 235, Magnolia is rich in history, featuring the Allee House among other notable archeological sites. Visitors can spend a pleasant afternoon exploring its three historically preserved homes, stepping back in time within its intimate boundaries.

13. Wilmington – A Weekend Worth Savoring

@cityofwilmde

Explore Wilmington, where the legacies of the Swedish settlers and the DuPont family enrich every corner. Discover cultural treasures like the Hagley Museum and the Delaware Art Museum, or take a nostalgic ride on the Wilmington and Western Railway. As a bonus, it's also the hometown of U.S. President Joe Biden, adding a contemporary note to its rich historical tapestry.

14. Bowers – Nothing but Pure Fun!

In Bowers, life revolves around the water. Known for both commercial and recreational fishing, it's the perfect spot to indulge in the fresh catch of the day at local eateries like JP's Wharf. Embrace the relaxed pace and savor the simple pleasures of seaside life in this charming fishing village.

TAGS: Delaware Small Town

Discover the Charm of Small-Town Delaware

01. Milford – Discover Craft Beer, Art, and Endless Festivals

02. Lewes – Step into Delaware’s First Town

03. Smyrna – Where History Echoes in Every Corner

04. Hockessin – Quaint and Utterly Enchanting

05. Rehoboth Beach – Dive into the Best of Seaside Living

06. Millsboro – Founded by Pioneers, Loved by Many

07. Delaware City – Come for the Waterfront, Stay for the Views

08. Dover – Get Ready for Fun in Delaware's Capital

09. Slaughter Beach – Memories of Summer Playgrounds

10. Little Creek – A Hidden Gem in Delaware

11. Laurel – Wrapped in Natural Splendor

12. Magnolia – Preserving Its Historic Borders

13. Wilmington – A Weekend Worth Savoring

14. Bowers – Nothing but Pure Fun!

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Discover the Charm of Small-Town Delaware

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01. Milford – Discover Craft Beer, Art, and Endless Festivals

02. Lewes – Step into Delaware’s First Town

03. Smyrna – Where History Echoes in Every Corner

04. Hockessin – Quaint and Utterly Enchanting

05. Rehoboth Beach – Dive into the Best of Seaside Living

06. Millsboro – Founded by Pioneers, Loved by Many

07. Delaware City – Come for the Waterfront, Stay for the Views

08. Dover – Get Ready for Fun in Delaware's Capital

09. Slaughter Beach – Memories of Summer Playgrounds

10. Little Creek – A Hidden Gem in Delaware

11. Laurel – Wrapped in Natural Splendor

12. Magnolia – Preserving Its Historic Borders

13. Wilmington – A Weekend Worth Savoring

14. Bowers – Nothing but Pure Fun!

Recommended

14 Free Things You Can Get at Airports

11 Celebrity Homes You Can Stay at Through AirBnB

Go to Bar Harbor For Outdoorsy Fun

Get inspiration sent straight to your inbox

About

EXPLORE

Get inspiration sent straight to your inbox