Rad’s Ultimate Travel Guide to Cape Cod, Massachusetts

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The Must-See Destinations of “The Hook”

As you load up an old rusty, four-door jeep with beachware and travel bags, a multi-hour drive seems much more bearable when you have one thing on your mind. Destination Cape Cod, Massachusetts. 

Nothing quite matches up to the anxious excitement of running directly to the water upon arrival. The appreciation of the trip lies within the scenic treasures filled by waterfront cottages and shadows of sinking telephone poles lining Route 6A.

Known for its magical dune-lined beaches, charming history and incredible seafood cuisine, the Cape delivers a captivating experience to travelers looking for a true escape. Timeless appeal, unique culture and geographical wonders equate to the ultimate beach getaway.  The hooked-shaped peninsula extends far into the Atlantic and contains dozens of towns each with their own distinct personality.

Historically, the Cape was the original landing point for the Pilgrims. After exploring the area during a five-week span in 1620, they decided to officially settle on Plymouth. Hyannis is famously known as home to the Kennedy’s who also played an essential role in preserving the historic Cape Cod National Seashores.

Above all, there is certainly no shortage of things to do here. Snap a few photos of the classic lighthouses in Chatham, take a ferry out to Martha’s Vineyard or have yourself a time in the Tip of The Cape known as Provincetown. The family-friendly and LGBT-friendly atmosphere creates a wonderful destination fit for a flawless weekend getaway or dreamy summer vacation.

Cape Cod Bars – A dive lover’s dream..

The high-end cocktail bars in the hotels of Wequassett and Chatham may suite the luxurious taste of some, yet the true bar scene of Cape Code is found in the dimly-lit, unadulterated dives of The Hook. From billiards and old jukebox tunes, to live music and karaoke with cross-dressing drags, Cape Cod has a nightlife with an oddly satisfying feel.

Rad’s Top Three Dives of The Cape

1. The Bombshelter – Wellfleet, MA

This cash-only watering hole serves ice cold beer from the grizzly owner named Steve who has a ferocious handshake. Put your name on the chalkboard for your line in pool. Also, don’t be surprised if a 30-person wedding after-party crashes the tiny venue during your game. This happened to me last time I was there when I was on the 8 ball..

Location: 50 Kendrick Avenue, Wellfleet, Massachusetts
Opening Times: Mon – Sun 11am – 11pm

2. Land Ho! – Orleans, MA

With its close connections to the community, this old-time favorite is as genuine as it gets in the Cape. The facade is covered with local business signs for a unique finish. Grab a brew and head to the Captain Walker Function Room which pays homage to the brave seamen who traveled through the northeast throughout history. Land Ho! is also known for its wicked seafood entrees and appetizers. Make sure to come hungry.

Location: 38 Main St, Orleans, Massachusetts

3. The Old Colony Tap – Provincetown, MA

This classic P-town dive comes equipped with a sunken ceiling, ancient nautical decorations and a kick-ass jukebox playing everything from The Doors to Kool and the Gang. Did I mention really loud live music is played by old hippies from the 60’s? It’s true, and it’s quite the entertainment. This dive bar treasure never fails as the place to go for a cold beer and a great time.

Location: 2202, 323 Commercial St, Provincetown, Massachusetts

Cape Cod Dining – The finest seafood in New England

Nothing quite captures Cape Cod cuisine like a succulent lobster roll or fresh-caught steamed lobster. Just by driving by the endless amounts of restaurants you will quickly find out that Cape Codians take their red crustaceans very seriously. Aside from lobster, the Cape offers every type of dish for the true seafood lover. From five-star dining to the quick bites of family grubbing, Cape Cod has it all.

Rad’s Top 3 Seafood Restaurants

1. PJ’s – Wellfleet, MA

This local family favorite has held its identify for generations, and is the perfect stop for a chowder on-the-go or seafood bucket for dining in. The seafood platter compromised of flounder, shrimp, scallops, whole clams with fries and slaw is a salivator at PJ’s. Top it all off with a classic cone of soft-serve ice cream.

Location: 2616 US-6, Wellfleet, MA
Opening Times: 11am – 9pm

2. The Impudent Oyster – Chatham, MA

An unrivaled raw bar that is sure to have you chomping at the bit for one seafood dish after another. The owner Peter bought the venue which was originally a dive bar named The Sign of the Surf. Within a few years he transformed it into an upscale restaurant that has become a go-to eatery in the Cape. Its unique charm is highlighted by the stained glass window above the entrance which was purchased from a church in Maine. It doesn’t hurt that the bustling bar scene promotes plenty of mingling after your superb seafood dinner.

Location: 15 Chatham Bars Ave, Chatham, Massachusetts
Opening Times: Thursdays – Mondays 11am – Late

3. Mac’s Seafood – Provincetown, MA

This Ptown gem serves incredible seafood plates and surprisingly delicious sushi. Mac’s Seafood’s open-deck patio is a great place to take in the cool breeze coming off the Cape Cod Bay. It has a bit of a modern, city-feel but the antique oars and fish paintings bring you right back down to earth.

Location: 85 Shank Painter Road, Provincetown, Massachusetts

Cape Cod Activities – An explorer’s sanctuary

From season to season, Cape Cod offers loads of things to do with activities that all seem to involve a picturesque backdrop. This geographical treasure truly embodies appreciating the simple things in life. Lace up some shoes, throw on some sunglasses and explore everything that the Cape has to offer.

Rad’s Top 3 Things To Do in Cape Cod

1. Explore the Dunes

Cape Cod is most known for its incredible lunar-like landscape. The golden dunes of the Cape make for the perfect off-road expedition allowing you to find your own peaceful paradise. Make sure to capture the draw-dropping views while you are out there. They are definitely Insta-worthy.

2. Cape Cod National Seashore Tours

Take a journey off the beaten path and explore over 40 miles of nature’s pristine beaches, trees and shrubs. Consider a guided tour with an expert such as Art’s Dune Tours to take part in kayak excursions and lighthouse tours during your stay. 

3. Biking in the Cape

The beauty of Cape Cod is the seemingly endless trails and roads that lead to marvelous lakes, ponds and other bodies of water. The relatively flat terrain makes for a perfect way to spend a day biking with friends and family. Local favorites include the seven-mile path along the Cape Cod Canal, four-mile Shining Sea Bike Path and the adventure-packed eight-mile course of the Cape Cod Province Land Bike Trail in Race Point.

Cape Cod Bike Hire
Denis Cycle Center Location: 249 Great Western Rd South Dennis, Massachusetts
Orleans Cycle Location: 26 main street, Orleans, Massachusetts

Pro-tip: Bring your bag of golf clubs and shoot a round at one of the three dozen golf courses on the Cape.

Cape Cod Golf Courses
The Captains Golf Course Location: 1000 Freemans Way, Brewster, MA
Cranberry Valley Golf Course Location: 1933, 183 Oak St, Harwich, MA
Dennis Pines Golf Course Location: 50 Golf Course Rd, South Dennis, MA

Whether you are planning a couples retreat, weekend getaway or extended summer vacation, Cape Cod is sure to deliver. It’s necessary to plan multiple trips throughout the year to truly explore the unique peninsula. Even if you’ve been spoiled by Southern California’s beaches for the majority of your life, I can attest that nothing quite compares to the memories made in the quaint beach-towns of Cape Cod Massachusetts. Head to the map below to book your stay today, you’ll be glad you did. 

Feature image: Race Point Lighthouse. Photo credit: m01229

Accommodation near Cape Cod

Rad Season is providing you with rentals and hotels at the lowest prices available online. Book your stay near Cape Cod using the map below!

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Harry R Bennett III

Harry R. Bennett III is a Los Angeles native who grew up addicted to playing sports. His love for the game of baseball eventually landed him several scholarships to play college ball across the United States. After receiving his B.A. in journalism, he pushed himself out of his comfort zone and moved to New York City in an effort to pursue his passion in the sports industry. Bennett has worked with major companies such as Fox Sports and Major League Baseball and has written for several online publications covering a variety of sports content. Although his playing days are over, he enjoys the endless pursuit of competition from athletics and action sports. In his free time, Harry can be found surfing, snowboarding, golfing, playing basketball and selling homes in Brooklyn. Follow him on Instagram @hb3_estates


    One thought on “Rad’s Ultimate Travel Guide to Cape Cod, Massachusetts

    1. Excellent site. A lot of helpful information here.
      I am sending it to some buddies ans also sharing in delicious.

      And naturally, thank you to your effort!

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