Martha’s Vineyard in October: A Cozy Honeymoon Escape (and What to Expect)

When we were planning our honeymoon, Cabo San Lucas was the dream. But fate had other plans. Just two weeks before our wedding, Hurricane Odile devastated the Baja California Peninsula. We shifted gears and found ourselves on Martha’s Vineyard in October. It wasn’t the sunny beach vacation we envisioned, but it turned out to be a magical, cozy escape, and we’re excited to share our experience planning a trip to Martha’s Vineyard without a car.

Note – all photos in this post are from early October 2014!

From Cabo to Cozy: Our Martha’s Vineyard Honeymoon Story

Our original honeymoon plans were upended by Hurricane Odile, a truly scary time. We were so relieved to hear everyone was safe, but it meant scrambling for a new destination. My amazing work team even offered their Key West beach houses! Ultimately, we wanted something relaxing, somewhat local, and affordable. Martha’s Vineyard in October checked all the boxes. I thrive in coastal New England and Martha’s Vineyard is the perfect place. There’s something to do for everyone.

Martha’s Vineyard in October: Setting Expectations

Martha’s Vineyard in October is a different experience than the bustling summer months. We knew we weren’t going for beach weather, and that was key to enjoying our trip. We experienced a mix of weather: some rain, some clouds, and definitely some wind. There was even a storm offshore that briefly shut down the ferries. If you’re planning a trip to Martha’s Vineyard in the fall, be prepared for varied weather and pack accordingly (think sweaters, layers, and maybe a raincoat).

The Perks of Visiting Martha’s Vineyard in the Off-Season

Despite the unpredictable weather, visiting Martha’s Vineyard in October had its own unique charm. The island was much quieter, with fewer crowds. Sometimes we were the only ones on the bus! This created the perfect atmosphere for a relaxing honeymoon. We could explore at our own pace and truly soak in the island’s beauty. While we loved the tranquility, we did promise ourselves we’d return in the summer for a different perspective – more on that trip coming soon!

Martha’s Vineyard History: More Than Just Vines

It’s a common question: Why is it called Martha’s Vineyard when there aren’t any vineyards? The island’s original name, given by the Wampanoag Tribe, was “Noepe,” meaning “land between the streams.” When a British explorer “discovered” it, he renamed it after his daughter, Martha, and added “Vineyard” due to the abundant wild grapevines along the coast. It’s a fun piece of Martha’s Vineyard history.

Getting Around Martha’s Vineyard Without a Car

We flew JetBlue from JFK to Martha’s Vineyard Airport (MVY), a charmingly small airport. Getting on and off felt like a private jet experience! For getting around the island, we relied on the affordable and efficient bus system.

Martha’s Vineyard Bus System: A Car-Free Guide

The Martha’s Vineyard bus system was incredibly easy to navigate. Being used to public transportation in the city, it felt natural to us. You can now conveniently purchase tickets online and download them to your phone. Check out the Martha’s Vineyard Transit Authority (VTA) website for schedules and routes. If our parents can use it, anyone can!

Story time: when we were traveling, we took hummus with us. Brought it onto the plane in New York and snacked all the way to the vineyard. On the way back, we stopped at a grocery store, picked up some hummus, and went to the airport. Our poor hummus was confiscated because it’s defined as a ‘paste’! We were so mad and confused. While the airport is very tiny, nothing gets by their security haha.

Where to Stay on Martha’s Vineyard in October

We stayed at The Dockside Inn in Oak Bluffs. It was a perfect no-frills, boutique hotel with a great location. We could easily walk to shops, restaurants, the Gingerbread Houses, the ferry, and bus stops. The hot tub was a welcome bonus, especially with the cooler October weather.

Where did we stay on Martha’s Vineyard?

We stayed at a cute hotel called The Dockside Inn. It was a no frills, boutique hotel located in a convenient part of Oak Bluffs. You can walk to everything you want to explore in the town: the food, the Gingerbread Houses, the ferry, and bus stops. They even had a hot tub on premises. Much needed considering the weather was a little chilly.

Things to Do on Martha’s Vineyard in October: Our Itinerary

Oak Bluffs was our home base, but we made sure to explore other parts of the island.

Oak Bluffs Highlights:

• Gingerbread Houses in Trinity Park: A must-see!
• Inkwell Beach and Seaview Ave: A beautiful walk along the coast.
• Shopping: Plenty of souvenir shops to explore.
• Mocha Motts: Our daily coffee stop.
• Linda Jean’s Restaurant: Delicious for breakfast, brunch, and dinner.
• Lookout Tavern: Voted the best lobster roll on the island (and we agree!).

Exploring Edgartown:

• Downtown and North Water Street: Admiring the classic New England architecture.
• Harbor View Hotel: Drinks on the porch with stunning views.
• The Newes from America: Great for lunch and dinner (try the steak and cheese!).
• Mad Martha’s Ice Cream: A Martha’s Vineyard classic.

Adventures Beyond Oak Bluffs and Edgartown:

• West Chop Lighthouse: Our bus driver provided a fun history lesson on the way (did you know Martha’s Vineyard was once part of New York?).
• Menemsha and Larsen’s Fish Market: We rented a car for a day trip to Menemsha for Larsen’s lobster rolls (even though the sunset was cloudy).
• Aquinnah Cliffs and Gay Head Lighthouse: Absolutely stunning! We even brought a slice of our wedding cake to enjoy at the overlook.

Martha’s Vineyard in October: A Honeymoon to Remember

Our Martha’s Vineyard honeymoon wasn’t the Cabo trip we initially planned, but it was perfect in its own way. We embraced the cozy atmosphere, the quiet charm of the island in October, and the opportunity to explore at our own pace. We highly recommend visiting Martha’s Vineyard in the fall for a unique and relaxing experience.

Have you visited Martha’s Vineyard in October or any other time of year? What were your favorite experiences? Share your tips and recommendations in the comments below!