As with much of the North Shore, Riverhead’s early inhabitants were Algonquin-speaking Native Americans when settlers arrived in the 1600s. But it took until the aftermath of the American Revolution for the town to be mapped out and founded in 1792. The 19th century saw Riverhead the hamlet emerge as the commercial hub. That history of commercial strength laid the foundation for a cultural scene you might not find elsewhere on the North Shore. The jewel in the cultural/historic crown is the lovingly restored Suffolk Theater on East Main, which brings in established comedians like Bob Saget and Paul Reiser; old-timey chart-toppers like Mary Wilson and Art Garfunkel; and novelty acts such as the Chippendales male revue and a woman who impersonates Barbra Streisand. On the same street is the well-regarded Long Island Aquarium. Today, Riverhead is on the move, a 21st-century success story with a welcome diversity and attractive property values.

Main Street is replete with options. Jerry & the Mermaid is the quintessential spot for seafood, with Blue Point oysters, lobster rolls, seafood bisque, and baked stuffed clams. Farm Country Kitchen has a pretty patio, fresh salads, and a water view. The Star Confectionery Luncheonette is just as it sounds, a nostalgia trip in a corner location serving open hot turkey sandwiches, malted milk, and banana splits. There’s ethnic food to be found as well: Il Giardino for Italian, Haiku for sushi, and Turkuaz Grill, which is top-rated for shrimp and lamb — and for its waterfront location. Tanger Outlets is the go-to for retail therapy. There you’ll find high-end apparel (Perry Ellis, Armani, Polo Ralph Lauren, Steve Madden, Ann Taylor), sportswear (Puma, Asics), and young adult clothing (Hollister, Abercrombie & Fitch). And you can fill your new home with housewares from West Elm, Pottery Barn, and Restoration Hardware.