This Quiet, Sandy Massachusetts Beach On Cape Cod Hides Behind A Difficult But Wildly Rewarding Trail

For anyone who loves a walk on the beach, the Great Island Trail on the Outer Cape region of Cape Cod may make both feet and heart go pitter-patter. That's because the 3.9- or 8.8-mile trail (depending on which loop you take) takes in some of the best ocean views and sandy dunes in Massachusetts. It starts a few miles west of downtown Wellfleet, the beachy beauty of Cape Cod without crowds. From the fast-filling parking lot of Chequessett Neck Road, the trail heads south through an aromatic pitch pine forest to reach the beach. A few steps in from the parking lot, find the grave of a Wampanoag woman, now covered with shells, pebbles, pinecones, and other talismans. Discovered in 1953, the 400-year-old bones below remind hikers that they are walking on Native land.

From the beach, the trail continues south along a tombolo known as "the Gut," for the stomach-shaped bulge of Herring River alongside. Here's where the Great Island Trail fully opens to rich salt marsh areas that are one of the hike's major features and a habitat for fiddler crabs, herons, egrets, and the famous Wellfleet oysters — one of the 12 top experiences in Cape Cod. From here on in, the trail remains somewhat open to the elements, magnifying whatever the weather is for the day, especially the sun, making protective lotions, sunglasses, head coverings, and water important accoutrements. On the flip side, gusty ocean winds may bring significant chill to an otherwise warm day — depending on the season of your hike, layers might be a good idea.

At the end of the Gut, Great Island begins with a fork in the trail — one branch heading east toward Samuel Smith Tavern Site and another south toward Jeremy Point. When judging distance and stamina, keep in mind the trek's terrain as well. The soft sand underfoot pairs one step forward with a half step back, increasing the effort. That tavern loop is the shorter of the two and leads to the Samuel Smith Tavern Site, where whalers congregated between 1690 and 1740. Nothing remains above ground besides a marker, but any disappointment is mollified by sweeping cliffside views of Wellfleet Harbor and the shade of the pine trees that cover this part of Great Island.

If you head straight at the fork, instead, the route takes you south on a longer stretch along the beach toward Jeremy Point. The closer you get, the more sandy and windswept the landscape becomes. How far you can go depends on the tide. When it's out, you can go much farther on the exposed sand; just be sure to return before the tide does. Otherwise, swing back east and north along the official trail and back among the pine trees before coming out among the sand dunes again. Eventually, this reaches another fork, where going right takes you to the tavern site, and straight, back toward the Gut. If you've still not reached your fill of beachside hikes, head 20 miles north to this wild Cape Cod stretch with sandy dunes and spectacular sunsets.