A Weekend In Martha’s Vineyard

We just got back from the most relaxing and dreamy long weekend in Martha’s Vineyard.

We packed our bags and the car and headed to the Vineyard with the boys and dogs for Indigenous People’s Day Weekend.

I wasn’t planning on sharing this trip here on the blog but Martha’s Vineyard really is too beautiful not to share. This trip marks our last October family weekend before John leaves for college next year. He brought his trusty polaroid and captured many memories.

Want to take a trip to the Vineyard with us? Read on for more!

What is Martha’s Vineyard?

Martha’s Vineyard is an island off of Cape Cod. It is part of Massachusetts. The island is 87.48 square miles and the 57th largest island in the United States. It’s a popular destination in the summer, particularly known for it’s beautiful beaches, the Black Dog, some filming locations for Jaws, and it’s famous residents, but there’s so much to know and love about the island.

The original inhabitants of Martha’s Vineyard were the Wampanoag people. In 1641, the Vineyard was purchased by Thomas Mayhew, an Englishman, and it is reported that he paid $200 for Martha’s Vineyard and Nantucket (another island off the Cape).

The Vineyard is composed of 6 different towns and each has it’s own unique feel and flavor. They are Edgartown, Oak Bluffs, Vineyard Haven, West Tisbury, Chilmark, and Aquinnah.

During my sophomore year of college I lived in Vineyard Haven and I took part in the Island Actors’ Workshop, stage managed plays and worked at the Black Dog Café. What a fun place to be in the summer!

Getting to the Island

We live on Boston’s South Shore in Scituate. So the ride was only about an hour and twenty minutes and then we took the ferry which is 45 minutes. It was a quick and easy journey to such a special spot.

By Boat

We took the ferry from Wood’s Hole to Oak Bluffs and our return crossing was Vineyard Haven to Wood’s Hole. When I was a student I only had a bike on the island but with a family and two dogs we decided we wanted a car. It’s pretty easy to book a spot for your car. You drive on and then for the 45 minute journey you can enjoy sunning yourself on the deck. See more about the ferry!

By Air

Martha’s Vineyard also has an airport and many commercial airlines fly here. Learn more about the airport here.

Where We Stayed

We rented the sweetest cottage in Menemsha (in Chilmark) for the weekend. It was important for us to bring our dogs. Max and Poppy LOVED it so much!

Menemsha is a small fishing village Up Island and we wanted to go here because it’s quiet and peaceful. The cottage was beautiful and had such a relaxed vibe. See more about the cottage here. The views were absolutely amazing from the cottage. Panoramic water views from the upstairs room and back deck.

We woke up to gorgeous sunrises and finished the day with glorious sunsets. I’ll share more about the area in a second, but first I want to share more about the cottage.

Marilyn, the owner, was a wonderful host. She provided such a beautiful home for us to relax but gave lots of suggestions for things to do and restaurants, too.

The cottage has two bedrooms and a funky little bar upstairs.

We played trivia up here and Conor enjoyed doing homework / video games from the round table.

I enjoyed reading on the front porch on the daybed. The lighting was lovely!

Meanwhile, Poppy’s favorite spot was the deck where she could watch the people and boats.

Menemsha

I think this has to be my favorite spot on all of Martha’s Vineyard. It’s so relaxing here. From the cottage we could could walk to so many places:

The Beach

Meneshma Beach is lovely. The boys played on the beach for ages. It was lovely that it was so close to the cottage.

Larsen’s

Larsen’s (for fresh seafood) – we had so many lovely things from here – crab cakes, lobster bisque, clam chowder, and warm lobster rolls for our last meal on the island. They have a mix of fresh caught seafood and fish and prepared food in their kitchen.

Shops & Galleries

There were two antique shops, two or three galleries, and two or three boutiques in walking distance to the cottage. The Homeport Restaurant and The Galley (ice cream stand) were already closed for the season. John and Luke got some fun shirts from Beatlebung and we loved Menemsha Blues.

The Coast Guard

As you know, Conor is thinking he’d like to be in the Coast Guard and considering the Coast Guard Academy. It was lovely to see the old Coast Guard station in Menemsha.

Menemsha Hills

One of our favorite spots was Menemsha Hills.

We drove here, but it’s a beautiful wooded walk that leads down to beach trails. Poppy hasn’t been able to walk as far but she LOVED this so much! I would have thought she was 6, rather than 13 on the walk!

Poppy living her best Vineyard life!

More of Our Favorites

Okay I feel like I’m rambling but I want to make sure to share all of our island favorites with you!

More Favorites in Chilmark

Well, Menemsha is in Chilmark so see above, but we also loved the following:

The Grey Barn – We’re longtime been fans of their Prufrock Cheese but didn’t realize it was made on the Vineyard. My friend, Sara, told me that they do tastings in the summer. They have a farm shop that is phenomenal.

We went on a rainy morning and it was humming. Fresh baked bread and pastries, delicious cheeses, and veggies. Highly recommend!

John made a friend outside while we filled our basket with goodies.

Chilmark General Store – This is the sweetest little general store with a lovely front porch to watch the world go by. They have great cookies and pizza, by the way!

Squibnocket Beach – This beach is really for residents of the town during the season but anyone can park off season. Conor wanted to go to this beach because his camp cabin was named after it. He loved it there. The day we went it was really windy and people were parasailing and surfing.

Lucy Vincent Beach – You also need a sticker from the town for this beach, but this was another stunning beach with lots of and lots of sand.

Favorites in Oak Bluffs

The boys rode on the oldest carousel in the country. I stood outside with the dogs. The gingerbread cottages are adorable to see in person! The history of Oak Bluffs is really interesting.

Conor enjoyed a swim in the ocean on Oak Bluffs Beach and we all enjoyed lunch at the Offshore Ale Company. They were so nice letting us eat outside with the dogs. The food was delicious and the decor inside was pure coastal Americana.

Favorites in Vineyard Haven

Vineyard Haven is a fun town full of great shops. One of our favorite shops is Coastal Supply Company. The owner, Anne-Marie, is so lovely and she has the shop filled with lovely gifts, apparel and home decor. It isn’t the best photo because it was raining but you get the idea.

Favorites in Aquinnah

Aquinnah is such a special place. We started off in the town looking at Gayhead Lighthouse.

The red clay cliffs are amazing. The Legend of Moshup says that the giant would bash whales against the cliffs making them red.

Aquinnah is home to the Wampanoag. You can feel such a sense of peace here.

We spent many hours up by the cliffs and walking the beach.

There was this really cool foam coming in the tide. It felt so cool and the seagulls were floating on the wind.

A Magical Trip

We were only on the island for 3.5 days but it felt like so much more. We spent so much quality time together and it felt wonderful to be in nature with our boys and our dogs. We all want to go back for another family visit. You can see a video of some of the beaches here.

Let’s Stay In Touch

On this trip we didn’t get to explore Edgartown that much. If you want to see more of Edgartown, you can read more about the HGTV Dream Home and see more of the beautiful town here.

Are you planning a visit to Martha’s Vineyard? If so, was this post helpful? Or, do you have some Vineyard favorites? If so, leave it in the comments section. It’s nice to share recommendations here!

Let’s stay in touch! Join our newsletter for access to exclusive content, our favorite projects, easy recipes, and fun tutorials. You’ll receive the best design secrets delivered directly to your inbox! Sign Up Here!