I've spent family summer vacations in Wellfleet, Massachusetts every few years since I went away to college. Wellfleet is tucked into the outer reaches of Cape Cod, bordered by the Atlantic Ocean to the east and Wellfleet Harbor (and Cape Cod Bay beyond) to the west. It's wild and rustic in a way that I really love, and it's a narrow strip of land that creates the most beautiful light throughout the day that culminates in enchanting sunsets.
The ocean side is part of Cape Cod National Seashore, which protects the dramatic dunes and has prevented the area from being built up. That cell service all but disappears when you dip over the dune and head to the beach is just a bonus. For reference, those are some pretty big dunes.
My favorite spots include Box Lunch, which makes sandwich wraps (called "rollwichs") that are perfect for toting to the beach. My go-to is the Chix Mex (with onions, no hots), and I've been ordering it (and nothing else) for years. Mac's on the Pier serves up a delicious seafood feast in my favorite outdoor setting anywhere, and the Beachcomber is great for happy hour as you just come off the beach.
PB Boulangerie Bistro serves up French pastries for breakfast (as evidenced here) and opens in the evening for full dinner service in the Bistro. And if that's not enough, there's incredible bread from the bakery and the whole exterior is pink! There's usually a line for breakfast, but I promise it's worth the wait.
Cahoon Hollow Beach, as seen from the Beachcomber (above and below), a legendary bar tucked into the dunes. It's only open seasonally (i.e. Memorial Day to Labor Day) and offers a great raw bar and live music.
Mac's on the Pier, which is perched right between the Wellfleet Marina and the bay. Grab a picnic table and take in the view below.
Mac's is BYO, so be sure to take along your favorite beer or wine to pair with seafood.
Lobster rolls, Wellfleet oysters, and clam chowder - oh my! Eating Wellfleets in Wellfleet is everything is cracked up to be.
Hiking around Wellfleet Harbor.
Sunset at Duck Harbor Beach, looking west across Cape Cod Bay.