A beautifully restored colonial-style home, painted blue with black shutters, in the historical district of downtown Laurel, Delaware. Editorial credit: Dee Dalasio / Shutterstock.com

6 Whimsical Towns to Visit in Delaware

Admitted as the First State to the Union back in 1787, the historic Delaware is indeed one of Northeastern America’s finest places of discovery. Celebrated for its Atlantic Ocean coastline, its small-town charm, and its fascinating stories of the early United States, Delaware is a delightful destination for anyone looking to find some of the very best of Americana. While such larger cities like Dover and Wilmington remain the State’s most well-known, the “First State” also has a number of equally captivating smaller towns, where beautiful surroundings, historic landmarks, and welcoming hospitality combine to create a most special vacation experience. So come see Delaware and its most splendid ambiance, which is sure to please the young and old alike!

Odessa

An abandoned mansion in Delaware.
An abandoned mansion in Delaware.

Situated in Northern Delaware’s New Castle County, Odessa is a charming town that allows guests to really get the feeling of time travel. Home to just under 400 permanent residents, Odessa was named after the Ukrainian port city in the 19th century, though its foundational roots date to the 1700s. Scenically located along the Delaware River, this inviting town delights all ages with its beautiful Historic District, where many of the preserved landmarks are listed on the National Register of Historic Places. Ranging from the 18th to 19th centuries, the attractions of note include the Collins Sharp House (1700), the Wilson Warner House (1769), and Cantwell’s Tavern (1822), amongst many more.

Enjoy a meal at the aforementioned historic Tavern, or at other local joints like the Corner Joints Café, while warm summers and winters make a stop here pleasant throughout the year.

Bethany Beach

A group of young women with paddle boards preparing to set out at sunrise on Bethany Beach, Delaware
Sunrise on Bethany Beach, Delaware. Editorial credit: David Kay / Shutterstock.com

One of Delaware’s most popular tourist destinations, the town of Bethany Beach sees around 15,000 visitors annually, even though its permanent population sits at just under 1,000! Situated right on the State’s Atlantic Coast, beautifully scenic and fun opportunities for swimming, sailing, and sunbathing never disappoint, while the endearing Bethany Beach Boardwalk is a delight for everyone. Delight in an assortment of tasty seafood eateries like Lili’s Place and Off the Hook near the water’s edge, while cute souvenir shops and tremendous panoramas fill out the rest. Add in the sights and sounds of live music performers and the opportunity to see some marine wildlife (including sand sharks), and it is easy to see what makes Bethany Beach such a wonderful place of discovery.

Delaware City

The Old Canal Shops at 129 Clinton St, Delaware City, DE.
The Old Canal Shops at 129 Clinton St, Delaware City, DE. Editorial credit: John Arehart / Shutterstock.com

Featuring a Historic District that is listed on the National Register of Historic Places, Delaware City can trace its modern history to the mid-1800s. Today, just under 2,000 inhabitants call this New Castle County town home, where a relaxing and pleasant feel of Americana is palpable. Full of great local shops and restaurants like The Saltbox and Crabby Dick’s near the Chesapeake and Delaware Canal, a quaint and welcoming atmosphere is never hard to find in Delaware City. Meanwhile, in the aforementioned Historic District, upwards of 200 buildings can be appreciated, spanning from the 19th to mid-20th centuries. Amongst the landmarks of note here include the Chelsea Home (1848) and the Fairview Home (1822).

And, of course, one cannot miss a trip to the Fort Delaware State Park, which immerses guests into Colonial America in an area spanning some 288 acres. Take in stunning natural views of Pea Patch Island and the Delaware Bay while learning more about the Revolutionary and Civil Wars.

Wyoming

An ice cream sign at the Peach Festival in Wyoming, Delaware
An ice cream sign at the Peach Festival in Wyoming, Delaware. Editorial credit: Foolish Productions / Shutterstock.com

Named after Pennsylvania’s Wyoming Valley, the Delaware town of Wyoming is a most lovely community with a modest population of just over 1,600 inhabitants. With a foundational history dating to the 1860s, Wyoming continues to maintain its farming and agricultural roots, and several local orchards and family-run farms continue to charm all who visit. Visit the Fifer’s Orchards store to pick your own locally grown fruits and vegetables, while the delightful summer Peach Festival should not be missed. Here the best in peach products, which include juice and ice cream, are a truly delectable way to entertain the young and old.

In addition this “Best Little Town in Delaware” has an alluring Historic District, where more than 300 distinct properties have been added to the National Register of Historic Places. These include the Railroad Station (1872) and the First National Bank, amongst many others reflecting a range of architectural styles from Victorian to Classical Revival.

Laurel

A group of young women with paddle boards preparing to set out at sunrise on Bethany Beach
A restored historic colonial home in downtown Laurel, Delaware. Editorial credit: Dee Dalasio / Shutterstock.com

Laurel is a most a charming small town in Sussex County, where splendid green spaces, cute ponds, and inviting parks create a most welcoming atmosphere. Established in the 1790s and with a modern population of nearly 4,000 residents, the pretty natural ambiance of Laurel is nicely complemented by its historic allure. Explore several buildings that have been listed on the National Register of Historic Places, ranging from the 18th to 19th centuries. Of note include the Old Christ Church (1772), and the Hearn Potato House (1900), amongst several more. And, of course, with Laurel’s relaxing and inviting outdoor beauty, even just a casual afternoon near ponds like Tussock and Chipman ensures a most peaceful and rustic American experience.

Milford

The Lighthouse Church off Route 1 in Milford, Delaware.
The Lighthouse Church off Route 1 in Milford, Delaware. Editorial credit: Khairil Azhar Junos / Shutterstock.com

Straddling the border of Kent and Sussex Counties, the historic town of Milford is one of Delaware’s oldest communities. Settled back in the 1680s, just over 11,000 call Milford home, where hot summers and cool winters are the norm. Located along the pretty Mispillion River, there is a great array of attractions waiting to delight all visitors here, from outdoor activities to cultural events. Take in the sights and sounds of the Fall Riverwalk Freedom Festival, which includes live entertainment, food vendors, and even a fireworks show. Meanwhile, the Milford Community Parade in October features colorful floats, marching and dancing groups, and other outstanding fun for the entire family.

From there, explore the Milford Vinyard Shipyard, a fascinating museum dedicated to many local Delaware artists and featuring several artifacts that highlight the State’s marine history. Add in great local restaurants like Surf & Turf Bar & Grill and the antique store Farmhouse 302, and the special American charm of Milford shines through brilliantly.

A Journey Through Delaware's History and Nature

Also known as the “First State,” Delaware is a cornerstone of the Northeastern United States, where stunning ocean views and fascinating history come together. Indeed, while major urban centers continue to attract much attention, Delaware’s smaller and whimsical towns are every bit as enticing for those looking for a memorable vacation experience. From the coastal beauty of Bethany Beach to the historic ambiance of Delaware City, these and other appealing Delaware towns reflect some of the very best of genuine Americana. Whether one is looking for a stunning natural wonderland or to be immersed in captivating episodes of American history, Delaware and these whimsical towns await!

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