Embarking on a whirlwind adventure, my partner and I spent an unforgettable two days on Cape Cod, reveling in the unique blend of coastal charm, outdoor activities, and cultural delights that this New England gem has to offer.

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Day One: Coastal Exploration and Culinary Delights

Morning: Biking the Cape Cod Rail Trail

Eager for adventure, we drove down to the Dennis parking lot for the Cape Cod Rail Trail. We chose this location to start with as it provides access to two great bike routes: Orleans/Wellfleet or Chatham. If you don’t have bicycles with you, don’t worry, there is a small bike shop adjacent to the parking lot where you can rent bikes, Barbs Bike Shop. Based on the time of year and day of the week, I would suggest calling a head to secure your rentals.


Using the route of old railroad tracks, the Cape Cod Rail Trail is a safe and leisurely way to enjoy a bike ride and see the Cape. Pedaling through quaint villages, cranberry bogs, and lush woodlands, the trail offered a perfect blend of nature and history.

Seaside Stroll in Chatham

Our adventure had us riding the Rail Trail toward the sleepy fishing village of Chatham. This took us about an hour to complete. Once there we secured our bikes and kicked off with a leisurely morning stroll along Chatham's Lighthouse Beach. The brisk sea breeze, coupled with panoramic views of the Atlantic, set the perfect tone for our coastal getaway.


Lunch: The Chatham Squire

Step through our doors, and you'll be enveloped in the cozy ambiance of a traditional New England tavern. Adorned with rustic woodwork, antique memorabilia, and nautical accents, The Squire is a place where stories are shared, laughter echoes, and friendships are forged.


They had lots of great choices including my favorite, a mouthwatering lobster roll, while my partner got a savory, juicy burger and we split their famous clam chowder! Good thing we were biking back to work off the meal!

Taking a leisurely ride back down the Rail Trail, it was just as fun as heading out. This really is an unbelievable resource that takes you on a safe, paved path, for more miles than most would want to ride! As I understand it, the path not only goes to Chatham but also Wellfleet via Orleans. That was definitely a longer ride than to Chatham. Next time, for sure! As we arrived back at the Dennis trail head, we returned our bike rentals and set off for the next adventure.


Evening: Sunset in Hyannis Harbor

We ended up driving into Hyannis main street, where we parked to take full advantage of the sights and sounds. As the sun began to dip below the horizon, we found ourselves in Hyannis Harbor. Boarding a sunset cruise, we enjoyed the changing hues of the sky and the silhouettes of docked sailboats, and even views of the Kennedy Compound! A perfect ending to our first day.

Dinner: The Naked Oyster

After our sunset cruise, we took a walk down Main Street in Hyannis where our culinary adventures continued at The Naked Oyster. We savored a delectable seafood dinner featuring locally sourced oysters and pan-seared Atlantic cod. The intimate ambiance and creative dishes made for a perfect evening. 


All in all, a great day seeing lots of what the Cape has to offer!


Day Two: Cultural Immersion and Outdoor Pursuits

Breakfast: The Kitchen Café

Located in the heart of Brewster on Route 6a, The Kitchen Café offers a great selection of tasty items to help fuel the day. My choice was the Bacon, Avocado and Goat Cheese on Pain D’Avignon Toast, so yummy!

Morning: Cultural Exploration at Cape Cod Museum of Art

Day two began with a visit to the Cape Cod Museum of Art in Dennis. Admiring works inspired by the region's landscapes and seascapes, we immersed ourselves in the rich artistic heritage of Cape Cod. Check their website out for the year-round events and exhibitions. They always have lots going on! Wish we had more time as I saw a few art workshops I would love to participate in.

Late Morning: Visiting Orleans

Stepping into Orleans, Massachusetts, felt like entering a coastal haven steeped in charm and tranquility. The quaint town greeted me with its historic architecture, lined with vibrant storefronts and blooming flower boxes that added splashes of color to the picturesque streets.

As I wandered through the town center, I was drawn to the inviting boutiques, art galleries, and locally-owned cafes, each offering a unique glimpse into the town's vibrant culture. The scent of salt air lingered in the breeze, a reminder of the town's close proximity to the sea.

Lunch: The Wellfleet Beachcomber

Ok…it’s not a trip to the Cape without a visit to The Beachcomber in Wellfleet. With an outdoor bar overlooking the Atlantic and an indoor bar in the heart of a former U.S. Lifesaving Station, it does not get any more authentic than the Wellfleet Beachcomber. Parking can be tricky and very limited depending on the time of year and day of the week, so plan a head.


Yeah, we bellied up to the bar…the RAW BAR! Nothing as good as Wellfleet Oysters when in Wellfleet! Partaking in the delicious food, while overlooking the Atlantic Ocean, with the sand in our shoes was simply amazing.

Afternoon: Adventure at Cape Cod National Seashore

As I stepped onto the golden sands of Marconi Beach, the salty breeze danced through my hair, carrying with it the invigorating scent of the sea. The rhythmic crash of waves against the shore echoed in the distance, creating a soothing soundtrack to accompany my stroll along the coastline. We sure walked off lunch!


The vast expanse of the Atlantic Ocean stretched out before me, its azure waters meeting the horizon in a seamless blend of sky and sea. Seabirds soared overhead, their cries mingling with the sound of the surf, while clusters of seashells and driftwood dotted the shoreline like treasures waiting to be discovered. With each step, I felt a sense of awe and reverence for the natural beauty that surrounded me, grateful for the opportunity to experience the untamed splendor of Marconi Beach on the Cape Cod National Seashore.

Evening: Dinner at the Ocean House in Dennisport

From the moment we stepped into the charming seaside establishment, we were greeted with warm hospitality and a relaxed coastal ambiance. The restaurant's panoramic ocean views provided a stunning backdrop for our meal, creating a serene and inviting atmosphere. From the succulent lobster bisque to the perfectly seared scallops, each dish was expertly prepared and bursting with flavor. Their attention to detail and commitment to quality ingredients was evident in every bite. To top off our meal, we indulged in decadent desserts that were the perfect sweet ending to a memorable dining experience. Damn, I love seafood…well actually, all food! Calories don’t count while on vacation, RIGHT?


Reflecting on our two days of fun and adventure on Cape Cod, we marveled at the diverse experiences the region had to offer. From coastal exploration and outdoor pursuits to cultural immersion and culinary delights, each moment was a celebration of Cape Cod's unique charm. As we bid farewell to this coastal haven, we carried with us cherished memories and a deep appreciation for the beauty and excitement that Cape Cod has to share.

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M. Parent

Written by M. Parent