7 of the Most Charming Towns in Delaware
John James Ingalls, the 17th-century politician, once quipped, "Delaware is a state that has three counties when the tide is out and two when it is in." Despite its diminutive size, the First State in the Nation is a prime example that good things come in small packages. This compact landscape is a fundamental part of its charm. Home to over 300 of the Fortune 500 businesses in the country, due to its tax-friendly status, employment opportunities abound. With a robust history going back to its Nanticoke and Lenape roots to the comforts of modernity, its appeal is universal. Uncover a few of the most charming towns to explore!
Bethany Beach
Located on the Atlantic Coast, this white sandy oasis was originally home to the Nanticoke people. Settled as a Christian campsite in 1901, it has become one of Delaware's most sought-after family-friendly beaches.
Less crowded than its counterparts, Rehoboth Beach and Ocean City, Maryland, it attracts families with its boardwalk and arcades, including the Shore Fun Family Center. The adults will enjoy visiting the nearby Salted Vines Vineyard & Winery. It offers tours, and the tasting room is the ideal place to chill out and sample its award-winning cabernets.
Everyone should head over to the James Farm Ecological Preserve. A short drive from Bethany Beach, locals refer to it as a wildland oasis. Walk the trails covering multiple types of habitats.
New Castle
Founded in 1651 by Dutch settlers, New Castle is considered part of the Philadelphia Metropolitan area.
Placed on the National Historic Registry in 1967, this sought-after region has a thriving downtown. The New Castle Courthouse is one of the oldest active court buildings in the US. The site is home to some of the nation's most impactful cases, including key decisions in the Underground Railroad. Visitors can listen to speakers at weekly conferences and even witness current trials.
New Castle's outdoor open spaces and recreational areas include Battery Park. This dog-friendly riverfront venue is perfect for picnics, birdwatching, and fishing.
Rehoboth Beach
Historically labeled the "Nations Summer Capital," it is a go-to beach destination for families from Washington, DC, and Philadelphia. Rooted in Native American culture, this charming town was the settlement for William Penn's legislative members.
A faster-paced alternative to Bethany Beach, it attracts visitors from up and down the Atlantic Coastline. Its mile-long boardwalk is home to the city's most popular attractions. Grab a slice at Grotto Pizza, a favorite of locals and visitors. Or treat your sweet tooth at Dolle's Candies. It's all tax-free, so indulge without the guilt.
If you want to relax away from the crowds, your answer is within easy driving distance. Cape Henlopen and Delaware Seashore, two beachfront parks, offer picturesque views worthy of Instagram. Enjoy the serenity of the white sand landscape, or borrow a bike provided by the Friends of Cape Henlopen and tour the trails.
For music lovers, Bottle & Cork awaits you only a couple of miles down the road. For over 80 years, this venue has featured acts including Blondie and Dave Matthews. Self-appointed the Greatest Rock and Roll Bar in the World, it also has open mic nights.
Lewes
Settled in 1631, Lewes is situated where the Delaware Bay meets Cape Henlopen.
Attracting adventurers who enjoy using the landscape and scenery as the backdrop for cycling and hiking, it is the site of the annual Dog Days of Summer event that incorporates athletics and family fun. Key spots include Breakwater Trail, Gordon's Pond Trail, and along the beach.
This charming town is highly walkable, with museums, shopping, and historical sites all within a compact location. Lewes Historical Society offers a variety of experiences to learn about its founding.
Are you in search of the fresh catch of the day? Then Matt's Fish Camp is your go-to destination. With oysters and shrimp, it's a Delaware staple. Extend your stay with a room at The Savannah Inn. This 1914 brick Victorian home has been fully renovated with an updated, elegant decor. Luxury amenities include gourmet breakfast as well as in-house spa services.
Arden
This quaint town is one of the more unique in the state. It was established as a single tax community that focused on equality. Will Price, the hamlet's founder, was motivated by a dream for a society that accepted everyone. With an original foundation focused on the arts, Arden attracts creative types from all over the country. Covering 160 acres, each home has historical significance and protections.
An architectural utopia, guided tours include stops at residences including Friendly Gables, The Lodge, Rest Cottage, Green Gate, The Second Homestead, and The Fels House.
Arden Gild Hall attracts musicians and productions and is one of the area's biggest draws. During the summer, the town hosts Shakespearean nights where individuals, both professional and novice, appear in some of the Bard's most memorable plays.
Smyrna
Originally referred to as Duck Creek Cross Roads, owing to its location that opens onto the Smyrna River, this town is part of Dover. Renamed in 1806 after the biblical name of a seaport in Asia Minor, Smyrna is packed with small-town charm.
The Smyrna Museum dates back to the late 1700s. Formerly referred to as the Barracks, this structure housed soldiers during the War of 1812. During the Civil War, it was the site of Delaware's Civil War lottery. Visitors can view historic artifacts and paintings, as well as guided seminars on local history. Best of all, admission is free.
Are you in the mood for some classic culture? The Smyrna Opera House is a local favorite. Originally built in 1870, it was fully restored in 2003. It hosts a variety of musical events throughout the year.
For those who enjoy a bit of spirit with their experience, the Painted Stave is the first small-batch distillery in Delaware. Tour the site for history of spirits and brews, and sample favorites, including their eponymous whiskey.
Odessa
This colonial town celebrates its heritage in architecture and lifestyle. Owing to its Indigenous roots, it was originally known as Apequinemy. Dutch explorers first settled it in the 1600s.
The Historic Odessa Foundation is an 18th-century font of information. Offering classes from cooking to costume, visitors can spend the day learning how to make continental cuisine and create Americana tapestries. All of the structures in Odessa are on the National Register of Historic Places. Guided walking tours recreate a typical day in the life of the founding fathers.
If you are a fan of the holidays, Odessa's charm is amplified by its period decorations, caroling events in the town square, and Dicken's nights at Cantwell's Tavern.
The fact that Delaware is the second smallest state has not impeded its enchanting ability to become a much sought-after escape. From sandy beaches with biodiverse ecosystems to towns built upon Indigenous and colonial history, visitors have unlimited opportunities to fill their itineraries. Plan your next trip to this hidden gem of a state on the Atlantic coast to experience its charm for yourself.
