A Day on Martha’s Vineyard: Our Journey with New England Trips
Our adventure began early in Boston, where we boarded a comfortable shuttle provided by New England Trips. As we journeyed south, the scenic drive took us over the Cape Cod Canal via the impressive vertical-lift railroad bridge, a marvel of engineering that connects the mainland to Cape Cod. The bridge, known as the Buzzards Bay Railroad Bridge, is one of the largest of its kind in the world.
Arriving in Woods Hole, a quaint village renowned for its marine research institutions, we caught glimpses of the bustling harbor where dolphins, sharks, and whales are often subjects of study and rescue operations. The village is home to the Woods Hole Oceanographic Institution, a leader in ocean science and exploration.
From Woods Hole, we boarded the Steamship Authority ferry for a 45-minute ride across Vineyard Sound to Oak Bluffs on Martha's Vineyard. The ferry ride offered panoramic views of the Atlantic, with the salty breeze setting the tone for our island exploration.
A Brief History – Tribal Land
Martha’s Vineyard, known as Noepe by the Wampanoag people, has a rich history that predates European settlement by thousands of years.
The Wampanoag, the island’s original inhabitants, are believed to have lived on Noepe for over 10,000 years, sustaining themselves through fishing, farming, and seasonal migrations. Their deep connection to the land and surrounding waters shaped the island’s culture long before colonists arrived.
Today, the Wampanoag Tribe of Gay Head (Aquinnah) continues to preserve its heritage and maintain a strong presence on the island, particularly near the iconic Gay Head Cliffs.
Exploring the Island
Upon arrival, we opted for the three-hour narrated island tour, while some fellow travelers chose to explore independently. Our tour guide provided a wealth of information about the island's history, culture, and notable residents. The tour included stops in two of the island's six towns, offering a glimpse into the diverse character of Martha's Vineyard.
For those who prefer to explore Martha’s Vineyard at their own pace, a free island shuttle service is available, making independent touring both easy and accessible. Operated by the Vineyard Transit Authority (VTA), this seasonal service offers frequent routes connecting major island towns such as Oak Bluffs, Vineyard Haven, Edgartown, and Aquinnah.
Travelers can hop on and off at various points of interest, from lighthouses and beaches to shops, galleries, and scenic trails. It’s a flexible option for visitors who want more time at specific locations or simply wish to discover the island’s charm without the structure of a guided tour. Be sure to check current schedules and route maps at the ferry terminal or online before setting out for the day.
Edgartown
Our first stop was Edgartown, a picturesque town known for its well-preserved 19th-century architecture and charming harbor. We had 50 minutes to explore, during which we visited a local coffee shop and a unique bookstore. The town's harbor offered stunning views, and we took a leisurely stroll to the Edgartown Lighthouse, a historic beacon that has guided mariners since 1828.
Edgartown Books is a charming independent bookstore on Main Street in Martha’s Vineyard, known for its thoughtful selection of fiction, children’s books, and local titles.
Tucked just behind the shop is Behind the Bookstore (BTB), a cozy café offering breakfast, lunch, and craft coffee in a peaceful garden setting. It’s the perfect spot to sip a latte, browse new reads, and soak up the relaxed Edgartown atmosphere—all in one visit.
Gay Head Cliffs - Aquinnah
Our second stop brought us to the stunning Gay Head Cliffs in Aquinnah, where we had 15 minutes to soak in the sweeping 360-degree views of the Atlantic Ocean and the surrounding landscape.
These striking, multicolored clay cliffs are not only a geological marvel but also a sacred site for the Wampanoag Tribe of Gay Head, the island’s Indigenous people.
After admiring the breathtaking scenery, we explored a nearby cluster of native arts and crafts shops, where my wife found a few unique souvenirs to remember the visit.
Lunch at Lookout Tavern
After the tour, we returned to Oak Bluffs for lunch at the Lookout Tavern. Overlooking the harbor, the tavern is known for its fresh seafood and relaxed atmosphere. We enjoyed a bowl of clam chowder and fish tacos, savoring the flavors of the island.
Notable Residents
Martha's Vineyard has long been a retreat for notable figures. Our guide shared stories of celebrities and politicians who have called the island home, including:
- Jacqueline Kennedy Onassis: The former First Lady purchased a 340-acre estate in Aquinnah in 1979, known as Red Gate Farm.
- Barack and Michelle Obama: The former President and First Lady own a home in Edgartown, where they have spent several summers.
- Ted Danson and Mary Steenburgen: The actor couple resides in Chilmark.
- Spike Lee: The acclaimed director owns property in Oak Bluffs.
- Carly Simon and James Taylor: The singer-songwriters have deep ties to the island.
Our driver shared a remarkable personal story that underscored the island's tight-knit and welcoming nature. He explained that the Clintons while vacationing at a nearby mansion, extended warm invitations to his family for social gatherings. Their connection grew strong enough that the Clintons even arranged for the family to visit the White House—a gesture that left a lasting impression and highlighted the unique bonds formed on Martha’s Vineyard.
Martha’s Vineyard Land Bank
The Land Bank is a unique and vital organization dedicated to preserving the island’s natural beauty, rural character, and open spaces. Established in 1986, the Land Bank is funded through a 2% fee on most real estate transactions, which allows it to purchase land for conservation, public use, and recreation. Its mission is to protect the island from overdevelopment while ensuring that residents and visitors alike can enjoy its trails, forests, beaches, and farmlands.
Today, the Land Bank manages over 3,000 acres across Martha’s Vineyard, offering access to walking trails, scenic overlooks, and preserved habitats. Whether you're hiking through wooded paths, birdwatching in quiet meadows, or simply taking in the views, Land Bank properties help ensure that the Vineyard’s natural treasures remain open and unspoiled for generations to come.
They Kennedy Connection
Martha’s Vineyard has long been associated with the Kennedy family, who have deep ties to the island and nearby Cape Cod. Perhaps the most prominent connection is Jacqueline Kennedy Onassis, who purchased a large estate in Aquinnah in 1979. Her property, known as Red Gate Farm, became a private retreat where she spent her later years, and it remains one of the most iconic homes on the island.
Two notable tragedies also tie the Kennedys to the area. In 1969, Senator Edward “Ted” Kennedy was involved in the Chappaquiddick incident, where he accidentally drove his car off a bridge on Chappaquiddick Island, just off Edgartown. His passenger, Mary Jo Kopechne, tragically drowned. The incident raised questions about Kennedy’s actions and had lasting political repercussions.
In 1999, John F. Kennedy Jr., son of President Kennedy and Jacqueline Onassis, died in a plane crash along with his wife, Carolyn Bessette, and her sister. Their small aircraft went down in the waters off Martha’s Vineyard as they were flying to attend a family wedding. The tragedy marked another somber chapter in the Kennedy legacy, one deeply tied to the Vineyard’s history.
Return to Boston
After a day filled with exploration and discovery, we boarded the ferry back to Woods Hole and then the shuttle to Boston. The journey offered a perfect blend of natural beauty, rich history, and cultural insights, making it a memorable day trip.
Visitor Tips
- Book your trip with New England Trips in advance, especially during peak season. (New England Day Trips from Boston)
- Wear comfortable walking shoes and be prepared for changing weather.
- Respect local customs and the natural environment, particularly in areas of cultural significance.
- Consider exploring other towns on the island, such as Vineyard Haven and Menemsha, if time allows.
Martha's Vineyard offers a unique blend of scenic landscapes, historical landmarks, and a vibrant community, making it a must-visit destination for travelers seeking an authentic New England experience.