Like many of the places I have visited, Martha’s Vineyard first found its way onto my bucket list through a story. I had heard Michelle Obama mention in interviews and podcasts that the island was one of her family’s favorite summer destinations, and naturally, I became curious. More recently, seeing Martha’s Vineyard featured in the Netflix series Forever only made me want to experience it for myself even more.
This summer, I finally made it to the Vineyard, and it completely lived up to the picture I had created in my mind. The charming towns, and relaxed summer atmosphere particularly impressed me from the get go. And, as usual whenever I visit somewhere beautiful, I immediately began planning my imaginary life there and thinking, I should buy a summer house here, oh if only wishes were horses!
Getting to the Vineyard
The drive from Boston to Falmouth is about an hour and a half without traffic, although summer traffic heading toward Cape Cod can easily stretch it to two hours or more. For the ferry, I used the Steamship Authority, which is one of the most common and generally most affordable ways to reach Martha’s Vineyard. It is also the ferry service to use when you want to take your car onto the island, although vehicle reservations must be made in advance. I decided to leave mine behind. Since there is no parking directly at the Woods Hole terminal, we parked at the Thomas B. Landers lot for a daily fee. From there, a complimentary shuttle picked us up and dropped us off at the ferry terminal. The process was much easier than I had imagined, although I would still recommend arriving early so you are not rushing between parking, the shuttle, and boarding the ferry.
After taking two Dramamine tablets, I settled into a sunny spot and spent the 45-minute ferry ride basking in the summer sun. Before long, we arrived in Oak Bluffs.
Arriving in Oakbluffs
Our ferry arrived in Oak Bluffs, one of the island’s seasonal ferry ports. Stepping off the boat placed us right in the middle of one of Martha’s Vineyard’s liveliest and most recognizable towns. Oak Bluffs has a fun, historic feel, with its colorful gingerbread cottages, Ocean Park, busy streets, restaurants, and waterfront views. It felt cheerful and full of character without losing the relaxed atmosphere I had come to the island hoping to find.
The hotel I booked was in Edgartown, so after arriving in Oak Bluffs and taking a little time to look around, I boarded one of the Vineyard Transit Authority (VTA) buses and continued across the island. I had already planned to rely on public transportation, since the buses were free during my visit, and that made it much easier to leave the car behind in Falmouth. It turned out to be a great decision, the ride was simple, convenient, and saved me from having to worry about traffic or parking once I was on the island.
Edgartown felt noticeably different from Oak Bluffs. While Oak Bluffs was colorful, lively, and historic, Edgartown felt quieter and a little more polished. Its beautiful white homes, boutique shops, waterfront restaurants, and peaceful harbor gave it the feeling of an elegant little seaside town. It was calm, walkable, and exactly the kind of place that makes you begin casually checking summer-house prices you have absolutely no intention of paying
Staying at the Richard
I stayed at The Richard in Edgartown, and it ended up being such a lovely part of the trip. The boutique hotel has that elegant Martha’s Vineyard look. Located on Main street also made it easy to walk around Edgartown, explore the nearby shops, and return to the hotel whenever I wanted a break.
One of my favorite things about staying there was the breakfast – I probably had the best freshly made croissants of my life!
Martha’s Vineyard is much bigger and more varied than I had expected, and each town has its own personality. In Oak Bluffs, you can walk through the historic Campground to see the brightly painted gingerbread cottages, relax at Ocean Park, visit the Flying Horses Carousel, or simply stroll along the harbor and enjoy the energy of the town.
In Edgartown, some of the best things to do are also the simplest: walk along Main Street, admire the historic homes, explore the shops, visit Edgartown Lighthouse, and spend time by the harbor. You can also take the small ferry across to Chappaquiddick, where you will find quieter beaches, Mytoi Garden, wildlife areas, and Cape Poge Lighthouse. While exploring Edgartown, be sure to stop by Edgartown Books, grab a burger at Quarterdeck, and end your day with ice cream from Vineyard Scoops.
Farther across the island, the Aquinnah Cliffs are one of Martha’s Vineyard’s most memorable sights. The dramatic clay cliffs overlook the Atlantic and offer a completely different view of the island from the busy harbor towns. Beach hopping, biking, hiking, visiting farms, taking boat tours, and exploring the island’s galleries are also popular ways to spend your time.
What I loved most, though, was that Martha’s Vineyard did not feel like a place where I needed to rush from one attraction to another. Some of the best moments came from simply walking through the towns, looking at the houses, sitting near the water, and enjoying the peaceful pace of island life. Wrapped up my last night in the vineyard with a scrumptious grilled branzino at the 19 Raw Oyster Bar & Prime Steakhouse.
Until next time,
Happy Wandering!