Leave the car behind and set out along flat bike paths along the coastline as you ride from Oak Bluffs to remote Chappaquiddick Island (“Chappy”). Relax on the windswept beaches on the small island made famous by the Kennedys. The total ride is about 18 miles (9 miles each way), with a very short bike ferry to cross the water.
Embark on a delightful cycling adventure starting in the charming town of Oak Bluffs. Your first task of the day involves securing your trusty two-wheeled steed. Make your way to Anderson’s Bike Rentals, a local favorite known for its well-maintained bicycles and friendly service. There, you can select the perfect bike to accompany you on your island exploration. If, by chance, you spent the previous night closer to the scenic locale of Vineyard Haven, fret not! You’ll discover a variety of alternative bike rental options available within Vineyard Haven itself, ensuring a convenient start to your cycling escapade, no matter where you choose to reside.
The inaugural leg of your journey spans approximately six miles, leading you towards the captivating destination of Edgartown. Before setting off, consider packing or purchasing some delicious sandwiches to enjoy as a midday repast. As you pedal onwards, be sure to follow Seaview Ave, a picturesque route that hugs the coastline and offers truly breathtaking vistas of the sparkling ocean. Along this scenic path, you’ll encounter several soft, inviting sand beaches. Feel free to pause your ride and indulge in a relaxing break, soaking up the sun and enjoying the refreshing sea breeze. Approximately 3.5 miles into your ride, a significant landmark awaits: the iconic Jaws Bridge, forever immortalized in cinematic history as the location for the filming of the classic movie, Jaws. This bridge is a popular spot, and you’ll frequently witness locals and visitors alike taking exhilarating leaps into the cool water below.
Arriving in Edgartown:
As you approach Edgartown, Seaview Ave gracefully transforms into Beach Rd, which subsequently merges into Main Street, guiding you into the heart of this quaint and charming town. Edgartown exudes a distinctly different atmosphere compared to the bustling energy of Oak Bluffs, offering a more tranquil and serene ambiance. Take some time to wander through the town’s delightful streets, exploring the diverse array of shops and art galleries that showcase local talent and unique treasures. Alternatively, you can make your way to Lighthouse Beach for a pleasant stroll that leads to the iconic Edgartown harbor light, a beacon of maritime history and a picturesque sight to behold.
Before venturing onward to the serene island of Chappaquiddick, make a strategic stop at the Rosewater Market, a culinary gem renowned for its delectable offerings. Here, you can curate a delightful picnic basket filled with freshly made sandwiches, crisp salads, and a tempting selection of other delicious side dishes, perfectly complementing your island adventure. With your picnic provisions secured, prepare to embark on a brief but memorable ferry ride aboard the Chappy Ferry. This quick ride provides a seamless transition to the unspoiled beauty of Chappaquiddick, offering a unique perspective of the surrounding waters.
Exploring Chappaquiddick:
Upon disembarking the Chappy Ferry and setting foot on Chappaquiddick, you have just three miles to travel before reaching the idyllic shores of East Beach. To get there, simply stay on Chappaquiddick Road, which eventually becomes Dike Rd. Be aware that the final stretch of the road leading to the beach is unpaved, adding a touch of rustic charm to your journey. This road will lead you to the infamous Dike Bridge, a location forever etched in history due to the unfortunate incident involving Ted Kennedy in 1969.
Once you arrive at East Beach, find your perfect spot amidst the warm, fine sand and let the soothing sound of the waves wash over you. This pristine beach offers an ideal setting to unwind, relax, and immerse yourself in the natural beauty of Chappaquiddick. Feel free to spend as much time as you desire on the beach, whether you choose to simply bask in the sun, read a book, or take a leisurely stroll along the shoreline. You can walk for miles in either direction, discovering hidden coves and enjoying the tranquility of this unspoiled paradise.
More Adventures in Oak Bluffs:
Upon your return to Oak Bluffs, a wealth of additional activities and attractions awaits your exploration. Immerse yourself in the whimsical charm of the Gingerbread Cottages, a captivating village of brightly colored, cookie-cutter houses that seem straight out of a fairytale. Alternatively, find a comfortable spot on the grass in Ocean Park, a vibrant green space where you can often enjoy live music performances emanating from the picturesque Gazebo.
And of course, no visit to Oak Bluffs is complete without indulging in a well-deserved ice cream treat. Treat yourself to a jumbo-sized cone from one of the town’s numerous ice cream shops, such as the renowned Mad Martha’s Homemade Icecream, a local institution famous for its delectable flavors and generous portions. If you’re seeking a more substantial meal, Oak Bluffs offers a diverse selection of restaurants catering to a wide range of tastes and preferences.
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