Fenwick Island is part of a string of small Delaware beach towns - Fenwick, South Bethany, Bethany Beach - that locals call the Quiet Resorts. The shorthand distinguishes them from the louder Delaware beaches further north: Dewey Beach is famous for spring break crowds, Rehoboth for its cosmopolitan restaurant scene. The Quiet Resorts are something else entirely - family beaches with low-rise rental cottages, no boardwalk amusements, and only a handful of restaurants and shops. Fenwick is the southernmost of the three. Its proximity to Ocean City makes it slightly less quiet than the Bethanies, since some visitors stay in Fenwick to walk to Ocean City's nightlife. But the contrast at the state line still amazes first-time visitors. The Delaware side is dunes and one-story houses. The Maryland side is condos thirty stories tall.

The town is named for Thomas Fenwick, an English planter who settled in Maryland in the seventeenth century. Fenwick himself never lived on the island; the name came from his land claims. The whole peninsula was disputed territory during the eighty-year-long Penn-Baltimore border conflict, which ran from the late 1600s until Mason and Dixon finally surveyed the line in 1763-1767. The Calvert family, Lords Baltimore, claimed the entire Delmarva Peninsula. The Penn family, founders of Pennsylvania, claimed everything north of the Transpeninsular Line at the latitude of Cape Henlopen. Fenwick Island sat in the disputed zone. After the surveyors did their work, the island ended up split: most of it in Delaware, the southern portion in Maryland - the tip of Maryland's Atlantic coast at Ocean City. The state line still bisects the long sandy spit that the maps no longer call a barrier island, since a man-made boat canal inland disqualifies it on a technicality. Geographers argue about whether it counts; vacationers do not.

Local legend holds that Cedar Island, in Little Assawoman Bay west of Fenwick, was used by colonial pirates to bury treasure. The Delaware coast was a known haunt for outlaws hiding from authorities, and Cedar Island offered a small, marshy refuge with limited mainland access. No documented treasure has ever been recovered, but the local story has the right ingredients for a coastal legend. Cedar Island has almost washed under the bay now - the small island has shrunk steadily as sea levels rise and storms erode its low edges. Seal Island, also in Little Assawoman Bay, disappeared around 2010, its last sandbar submerged. Whatever pirates left here is now under three feet of brackish water. The vanishing islands are a small visible piece of the climate-change shoreline transformation that is reshaping the entire Delmarva coast - faster than any colonial pirate could have anticipated, and faster than the people who built houses here in the 1950s and 1960s expected.

Delaware Route 1, known as Coastal Highway, runs the length of the Delaware coast from the Christina River in Wilmington south to its terminus at the Maryland border in Fenwick Island. The road is the spine of the Delaware beaches: it serves Dewey, Rehoboth, the Bethanies, and Fenwick before crossing into Maryland and continuing south through Ocean City as Maryland Route 528. Between May 15 and September 15, every street in Fenwick Island requires a parking permit. The town does not want day-trippers from Maryland walking across the line to take its sand. DART First State's Beach Bus Route 208 runs in summer between Fenwick and Rehoboth, connecting to other Beach Bus routes and the Wilmington-to-Rehoboth Route 305. Inland from Fenwick, Delaware Route 54 heads west toward Selbyville, a small mainland town that handles most of the grocery and gas needs of the beach resorts in summer. The infrastructure is built to serve a town that triples in population on summer weekends.

In 2020, when the White House Coronavirus Task Force coordinator Dr. Deborah Birx was photographed at her Fenwick Island beach house during the Thanksgiving holiday despite the federal travel advisories her own task force had issued, the town briefly became national news. The photographs showed Birx walking on the beach with family members from out of town. The political fallout was significant; Birx eventually announced she would retire after the inauguration in January 2021. The Fenwick Island beach house, like many of the homes in town, is a family compound built for multigenerational summer visits. It is the kind of house that Birx and her husband had owned for years before her national appointment. The town itself drew no political conclusions; it kept being Fenwick Island. But the episode underscored something the town's residents already knew: Fenwick is a quiet resort because the people who own homes here want it to stay quiet, even when the people who own those homes happen to be coordinating a national pandemic response. The houses pass between generations. The town stays small.