
CLASSIC SPOTS
Explore the
Best of Cape Cod
At Classic Cape Real Estate, we believe that Cape Cod is more than just a place to live—it’s a place to experience. Whether you’re a local or just visiting, there’s no shortage of beautiful spots and hidden gems to discover. Here are a few of our favorite Cape Cod destinations that capture the essence of this special place.

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Beaches
Nauset Beach
Nature at Its Finest | Orleans/Chatham
I've been driving out on Nauset and surfing the shifting sandbars since the '90's and perhaps no place holds the culture of this area better. Even if you don't have an oversand permit, this beach is a great experience for all.

Local Tip:
If you drive on the beach, lower your tire pressure, you don't want to be that guy.
Beaches
Nauset Light Beach
Where History Meets the Sea | Eastham
No trip to Cape Cod is complete without visiting Nauset Light Beach, home to the iconic Nauset Lighthouse. This is the perfect spot for a leisurely day by the ocean, whether you’re soaking up the sun, walking along the shore, or exploring the nearby historic lighthouse. As the waves roll in, you’ll feel the experience of Cape Cod’s maritime history, with the sound of the surf and the beauty of the surrounding dunes reminding you why so many have fallen in love with this coastline.

Local Tip:
Visit during the early morning or late afternoon for the most stunning views of the lighthouse at sunrise or sunset.
Beaches
Sandy Neck
Bayside | Sandwich/Barnstable
Stunning sunsets and campfires at dusk make this a unique experience. At the tip of the peninsula is a scenic village with private homes overlooking Barnstable Harbor.

Local Tip:
The beach is rocky so bring your flip-flops
Beaches
Nauset Spit
"The Cut"
Also known as, "The Cut" or "Inlet", it's a magical spot no longer accessible by off-road vehicles. You can access by boat or other watercraft, however. Emily's favorite access is through Cable Creek in a tin skiff.

Local Tip:
Keep your eye on your anchor as the tide rips
Entertainment
Wellfleet Drive-In Theater
Classic Fun Under the Stars | Wellfleet
Step back in time and enjoy a night at the Wellfleet Drive-In Theatre, Cape Cod’s only drive-in movie theater. Since 1957, this local treasure has been providing old-school entertainment for visitors and locals alike. Pack some snacks, gather your friends or family, and settle in for a movie under the stars. It’s a nostalgic, fun experience that captures the timeless charm of summers on the Cape.

Local Tip:
Arrive early to explore the flea market on the weekends or grab a bite at the on-site snack bar for the full vintage drive-in experience.
Market
Ring Brothers Market
Where Quality Meets Community | Dennis
Ring Brothers Market is more than just a local grocery store—it’s a community staple. Known for its commitment to quality, this family-owned market offers everything from fresh produce and local seafood to specialty gourmet items. Whether you’re grabbing ingredients for a beach picnic or browsing the extensive wine selection, Ring Brothers captures the spirit of Cape Cod’s local charm and hospitality.

Local Tip:
Don’t miss their fresh-made sandwiches at the deli—perfect for a quick bite before heading to the beach.
Market
Cape Roots Market
Farm Fresh and Locally Sourced | Harwich Port
From my good friends, Brooke and Gabe, who brought you The Hot Stove Saloon, Cape Roots Market is your go-to spot for deli sandwiches, prepared meals, beer and wine with private party space and even live music! Grab an espresso and pastry from the Coffee Bar. Cape Roots provides a refreshing alternative to your standard grocery run.

Local Tip:
Be sure to check out their rotating selection of local baked goods and grab a cup of fair-trade coffee to go.
Market
Chatham Fish Pier
A Taste of Cape Cod’s Finest | Chatham
For a glimpse into Cape Cod’s working waterfront, visit the Chatham Fish Pier. Every day, local fishing boats return with the day’s fresh catch, offering a unique look at the area’s thriving fishing industry. Watch as the fishermen unload their hauls and experience the authentic maritime life that has sustained the Cape for generations. It’s a great stop for seafood lovers and those curious about the region’s deep connection to the ocean.

Local Tip:
Grab lunch at the nearby seafood shack for some of the freshest lobster rolls and fried clams you’ll ever taste.
Restaurants/Bars
Las Chidas
Authentic Mexican
My go to when I'm feeling tacos and tequila but it's so much more with a fun vibe and real deal Birria Tacos, it's a must.

Local Tip:
You won't find more knowledgeable staff, Meredith and Paula will craft your experience.
Shops
Nauset Surf
The Original | Orleans
Having worked there in my youth, I have a lot of nostalgia for the family and shop. Phil is a Cape surfing legend and with his daughters, Molly and Jamie, they have a classic surf shop and more. All you need for beach essentials, skate and surf and stylish threads as well.

Local Tip:
The Penny Sale is a Holiday must