The Zwaanendael colony lasted barely a year. Captain de Vries had sailed from the Netherlands with twenty-eight men to harvest right whales from the Delaware Bay and ship the oil back to Amsterdam. The settlement included a small fort, a brick smokehouse, and a tin coat of arms hung as a territorial marker. According to de Vries's later account, a Lenape chief took the tin coat of arms to make a tobacco pipe. The Dutch settlers complained. The chief was killed by other tribal members trying to appease the Dutch. The killed chief's family, in turn, retaliated by attacking the colony. When de Vries returned in December 1632, the colony was burned and his men were dead. The Zwaanendael Museum, a small brick building in downtown Lewes built in 1931 to commemorate the 300th anniversary of the founding, holds artifacts recovered from the colony site. The building is modeled on the town hall of Hoorn in the Netherlands - the home port of the original settlers. Delaware's first European settlement is now a small museum a block from a candy shop.

During the War of 1812, a British squadron blockaded Delaware Bay, demanding that the town of Lewes supply provisions. The town refused. On April 6 and 7, 1813, the British bombarded Lewes for twenty-two hours. The town held. One British cannonball lodged in the brick wall of the house at 118 Front Street, where it still sits, visible from the street - the house is now known as the Cannonball House and operates as a museum of the bombardment. The local militia, led by Colonel Samuel Boyer Davis, fired back from a small earthen battery and successfully drove the British squadron off. The historical preservation has kept Lewes layered with these moments. The Lightship Overfalls, a 1938 floating lighthouse moored on the Lewes-Rehoboth Canal since 1973, was the last lightship constructed by the United States Lighthouse Service. The Fort Miles Historical Association preserves the World War II coastal defense complex at Cape Henlopen, where the U.S. Army stationed sixteen-inch coast artillery to defend the Bay. Walking through Lewes is walking through four centuries of American military history.

Cape Henlopen, the headland just east of Lewes, marks the south side of the Delaware Bay entrance. The cape was crucial to colonial navigation - the first American lighthouse south of the Delaware River stood here from 1765 until it was destroyed by erosion in 1926. Cape Henlopen is now a Delaware state park with five miles of Atlantic beaches, the World War II Fort Miles complex, and a nature preserve with the largest piping plover population in Delaware. The Cape May-Lewes Ferry, a 70-minute crossing of the Delaware Bay between the two former whaling ports, has operated continuously since 1964. Three large ferries shuttle cars, trucks, and walk-on passengers between the two beach towns. The terminal at Lewes is at the mouth of the Lewes-Rehoboth Canal, near the Roosevelt Inlet. The ferry traffic alone keeps Lewes's economy partly nautical - the Cape May ferries arrive and depart roughly every two hours through the summer season. The Harbor of Refuge Lighthouse, built in 1926 to replace an older damaged structure, stands on a stone breakwater visible from the ferry. Lewes is one of the few American small towns where you can still take a working ferry instead of an interstate.

Downtown Lewes is organized around Second Street, the main commercial corridor that runs parallel to the historic harbor. The street holds small specialty stores, restaurants, ice cream parlors, the Zwaanendael Inn (built in 1926 and renovated multiple times since), and the Dogfish Inn - a trendy retro motel associated with the Dogfish Head Brewery, which is technically in nearby Milton but anchors much of the region's hipster cultural identity. Lewes Beach, on the Delaware Bay side of town, has calmer water and shallower drop-offs than the Atlantic beaches further east. It is popular with families and surf-cast fishermen. The Cape Henlopen ocean beach, a few miles east, has the surf. The town's overall feel is Colonial-historic refurbished into modern beach-town small-business: Federal-style brick houses converted to boutiques, the canal lined with shipyard-era buildings that now hold restaurants, the Lewes-Rehoboth Canal Towpath providing a walking and cycling route. The town is small enough to walk in an afternoon. The history is dense enough to take days to absorb.

Lewes runs on small-town annual rituals. The Great Delaware Kite Festival, held on Easter weekend at Cape Henlopen, has drawn kite enthusiasts and stunt-kite demonstrations to the Bay shore for over forty years. The Overfalls Lightship Opening Party, held the Friday before Memorial Day, commemorates the start of the summer season with live music, food, and a cash bar on the deck of the 1938 lightship. The Lewes Historical Society Complex on Shipcarpenter Street operates a Marine Museum, a country store, and walking tours of restored homes. The downtown Christmas parade takes place the first Saturday in December. The town has the kind of recurring calendar that builds long memory - the same families come to the same events year after year, and visitors who choose Lewes over Rehoboth tend to come back. The 2020 census recorded 3,266 year-round residents. The summer population easily quadruples. The historical layering, the working ferry, the Colonial brick - it all adds up to a Delaware town that feels older and quieter than its more famous neighbors to the south. The First Town has held that title for nearly four centuries.