A getaway to Cape Cod should start with a place that already knows the tides, the trails, and the ice cream shops worth your time. At Inn at The Oaks in Eastham, MA, we have spent years pointing our guests toward the parts of the Cape that never quite make it onto the postcards.
This blog is our own local map, beaches, back roads, and the bit of windmill history that makes Eastham our favorite corner of the peninsula.
Which Beaches Are Worth Your Time?
Coast Guard Beach often lands on best-in-the-country lists, and locals will tell you it earns every one of them. Wide dunes, cold Atlantic water, and enough sand to spread out even in July make it an easy favorite.
When the ocean side feels like a bit much, First Encounter Beach on Cape Cod Bay offers calmer water and a sunset that draws a small, loyal crowd of regulars, us included. Pack a blanket and arrive an hour before the light turns gold. We will admit we’re biased, but we think this beach alone justifies a getaway to Cape Cod.
What’s Our Story?
Eastham has been quietly historic since 1651. That year, a small group of dissatisfied Pilgrims left Plymouth and decided to stay put here instead. The Eastham Windmill has been turning since 1680, making it the oldest working windmill on the Cape.
The Swift-Daley House Museum keeps the town's eighteenth-century daily life on display for anyone curious enough to ask. Did you know that First Encounter Beach carries its own weight of history, too?
It was the site of the first meeting between the Pilgrims and the Nauset people. Meanwhile, our own inn has a chapter in that story, as well. Sarah Chipman built this house in 1893, not long after she was widowed. She named it The Overlook for the water view it still has today. We just added the coffee. Guests still ask to see the original overlook the name refers to, and we’re always glad to show them.
Planning a Proposal, Anniversary, or Elopement?
Eastham has a way of making a moment feel bigger than it is, in the best way. Naturalist Henry Beston wrote some of his most quoted lines about this stretch of coast. It is easy to see why, once you have watched the light change over the dunes at Coast Guard Beach.
Couples planning an elopement or a quiet anniversary weekend tend to gravitate here, and we don’t blame them. There are fewer crowds and fewer people telling you what to do and where to go. If privacy matters most, our Carriage House sits just steps from the main house. It has its own entrance, its own charm, and its own quiet.
Where Should You Eat After a Day Outside?
Arnold's Lobster & Clam Bar earns its reputation honestly, with fried clams and a lobster roll worth the trip. In addition, Red Barn Pizza covers the rest of the week: pizza, burgers, and a beer list worth arguing over.
Start the morning at Hole-in-One for hand-cut donuts. End most nights at Nauset Ice Cream, which stocks more than thirty flavors and often runs out by Thursday. Finally, Eastham's stretch of Route 6 has more good food than any one visit can cover. Plan your appetite accordingly. Portions run generous, and seconds are more common here than anyone likes to admit. We will not judge a second trip.
What Else Is Nearby on the Outer Cape?
Eastham sits on the quiet end of the Cape, but Orleans, Wellfleet, and Brewster are all a short drive away. Then you have the ferries to Martha's Vineyard, and Nantucket is close by. Whale watching, extra shopping, and a change of scenery are all within easy reach if you want to wander further. The beaches and ponds outside the door tend to win. We’re always happy to point you in the right direction, whether that is a ferry schedule or more beach time.
Ready for Your Own Corner of Eastham?
Every good getaway to Cape Cod needs a place to come home to after the beach and the ice cream. At Inn at The Oaks, that is exactly what we have built. Quiet rooms, a porch made for evening conversation, and a staff that knows which beach lot fills up first. Come see it for yourself. We will have the porch light on and a getaway to Cape Cod waiting that feels entirely your own. Reserve your stay, and let Eastham, MA do the rest.
Updated 2026.
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