Settled by the Dutch in 1631, Lewes is a charming coastal community and as the earliest settlement in Delaware goes by the nickname of ‘The First Town in the First State’. Nestled between the beautiful beaches of Cape Henlopen State Park and wetlands of the Great Marsh Preserve, the town is centered around the Lewes and Rehoboth Canal and populated with picturesque historic buildings like the Ryves Holt House, built in 1665 and thought to be the oldest structure in the whole state. Far from a sleepy seaside town, Lewes is home to a vibrant community of local restaurants and boutiques and events like the Historic Lewes Farmers Market.
Located at the start of the Broadkill River, Milton’s short distance from Delaware Bay and riverside setting made it an important shipbuilding town in the 18th and 19th century and today the quaint small town’s Victorian heritage is still evident – Milton’s Historic District is home to nearly 200 registered historic buildings. The town has plenty for lovers of the outdoors too, with canoeing and fishing opportunities awaiting on its ponds and waterways and for fans of fine ale, Milton is also the home of the Dogfish Head Brewery which offers tours its facilities and tastings of its popular craft beers.
For quintessential small town America in northern Delaware, look no further than Smyrna – a picturesque community just a short drive north of the state capital Dover. Located on the banks of the beautiful Duck Creek and Lake Como, Smyrna is both proud of its past – evident in its beautifully preserved historic buildings like within the Duck Creek Village historic district – and forward-looking with cultural venues like Smyrna Opera House, which first opened over 100 years ago and added an art gallery in 2003; while the salt marshes of the nearby Bombay Hook National Wildlife Refuge are an easy getaway for lovers of nature.
Dating back to the 1660s and rich in history, Odessa boasts claim to one of the most unspoiled colonial townscapes in the nation – in fact much of the town is a National Historic District and the Corbit-Sharp House, a grand Philadelphia Georgian-style structure built in 1774, is a National Historic Landmark. Home to just under 400 people, Odessa is small but full of charm with a friendly vibe with the Appoquinimink River which flows past the town providing kayaking and wildlife-spotting opportunities and the historic Cantwell’s Tavern, first opened in 1822, perfect for dinner and a few well-deserved beers after a hard day on the river.
Located to the south of Lewes and Cape Henlopen, Rehoboth Beach is a much-loved seaside town that despite having just under 1,500 year-round residents sees its summertime population swell to around 25,000 during peak season when visitors flock the lovely community. Known for its pristine coastline, Rehoboth Beach has been bestowed with a whole host of accolades testifying to its beauty including being listed amongst USA Today’s 10 Best Coastal Small Towns and its mile-long boardwalk named one of Coastal Living Magazine’s 10 Great Coastal Boardwalks in 2013, while the picturesque town is also home to an eclectic community of shops and restaurants and events like the annual Sea Witch Halloween and Fiddler’s Festival.
Just a few miles downriver from Delaware’s biggest city Wilmington is New Castle – an historic town home to just over 5,000 people located on the banks of the Delaware River. Founded in 1651, the town became Delaware’s first state capital in 1776 before status was handed over to Dover the following year and the state’s first capitol building – the stately New Castle Court House built in 1775 and now a museum – can be visited today. Many of New Castle’s most beautiful places are clustered around the Court House and the river edges in an area referred to as Old New Castle including the Old Library Museum and Amstel House Gardens.
Boasting small town charm and a rich history, Georgetown was first founded in 1791, when residents in the Sussex County area petitioned to have the county seat moved from neighboring Lewes to a more central location. Georgetown’s central hub, The Circle, is listed on the National Register of Historic Places and home to a lovely fountain and the beautiful redbrick Sussex County Courthouse, built in 1839. The town has a lively cultural scene too: every other year, Georgetown is the site of Return Day, a traditional festival unique to Delaware, which kicks off with a concert and ox roast at The Circle.
Located on the Delaware River across from New Jersey, Delaware City is a beautiful town rich in history and culture. Nestled around the eastern banks of the Chesapeake and Delaware Canal, the pretty port town is home to a whole host of quaint buildings such as the Sterling Building, a hotel dating back to the early 19th century located on Delaware City’s scenic waterfront, while Pea Patch Island – home to Fort Delaware, a Union fortress dating back to 1859 used as a prison for captured Confederates during the American Civil War – is just a short ferry ride away.
Nestled on the banks of the Indian River, the rural riverside hamlet of Millsboro is amongst the prettiest towns that southern Delaware has to offer. Although the town was officially founded in 1860, the land on which Millsboro lies was actually settled as early as 1792 and before that, was home to the Nanticoke tribe whose traditions and culture are celebrated at the town’s Nanticoke Indian Museum. Today, boating, fishing and crabbing can be enjoyed on the Indian River during warmer months, while Millsboro’s charming downtown is home to cute antique stores and restaurants offering seafood and good old southern fare.
With its beautiful views out over the Atlantic Ocean, tiny but scenic boardwalk and lively summer cultural calendar, Bethany Beach – which alongside the neighboring coastal communities of Fenwick Island and South Bethany is often nicknamed The Quiet Resorts – offers a peaceful, laidback alternative to the more bustling towns of Lewes and Rehoboth Beach. Fun activities come in the form of the summertime Bethany Beach Farmer’s Market and the Bethany Beach Boardwalk Arts Festival held each September while lover of nature take advantage of the town’s proximity to the beautiful Assawoman Bay State Wildlife Area.