5 Things to Do in … Nantucket

The small island offers big charm and lots of cool things to do, from strolling cobblestoned Main Street to pedaling along the beaches. PEOPLE photo editor Regan Stephens shares her top picks for maximum fun


Rent a bike downtown at Young’s or Cook’s and choose your adventure. With 32 miles of scenic bike paths covering the Island, head for the rose-covered cottages of Sconset, the secluded beaches of Dionis or my favorite 6-mile cruise to Madaket. On the way out of town, stop by Something Natural on Cliff Road and grab a sandwich – made on freshly baked bread (get the herb!) – and a chocolate chip cookie to go. You’ll pass ponds, untouched conservation land and the Madaket Mall (the "take it or leave it" treasure trove found at the Island’s trash dump). Once you get to the end, stay for a picnic and a dip before pedaling back. Pro tip: Madaket beach is also Nantucket’s prime place to see a spectacular sunset.