Starting in the 19th century, Riverhead the hamlet began emerging as the commercial hub for Riverhead the town. However, since 2012—when the downtown area was recognized on the National Register of Historic Places—business, as it were, has been booming. A legacy of mercantile strength laid the foundation for a blossoming cultural scene you might not find elsewhere on the North Shore. Erected in the 1930s and lovingly restored, the Art Deco Suffolk Theater is the centerpiece of Riverhead’s arts district, hosting a lineup of musical acts, comedians, and other performers. Despite a lack of water-based endeavors—at least when compared to points further east—the Long Island Aquarium more than compensates with plenty of exciting exhibits for the aspiring marine biologist in your heart. After all, setting sail on a schooner is nice, but where else on the North Fork are you going to hang out with penguins?

When it comes to food, Main Street in Riverhead is positively packed with prospects. A vast array of cuisines are represented by countless formal and fast-casual eateries, some of which even enjoy a waterfront setting. Seafood, salads, banana splits—whatever you’d want, and more, are waiting there to be consumed. Good times are brewing in Riverhead as well, with craft beer makers pouring pints all over town. If you’re not so much into drinking ales, lagers, and the like, there are also vineyards for wine, distilleries for spirits, and orchards for hard cider. During the fall months, apple picking becomes an activity at those same orchards. For those searching for retail therapy, outlet stores for nearly every apparel or houseware brand you can think of are right outside downtown Riverhead.