Martha’s Vineyard

Edgartown Harbor Light.

(Photo taken by Hunter on 35mm film)

Martha’s Vineyard is one of the iconic destinations and oases of the New England area. It feels like a rite of passage to make at least one trip out to the island as a true New Englander, and the experience does live up to the hype. Hunter and I visited for a long weekend to celebrate our anniversary a few years ago. Most recently, we took a day trip out to the island with a group of friends this past summer. It is on our bucket list to someday rent a house and spend a week out there with friends. I read Summer on the Bluffs by Sunny Hostin this summer, and it inspired me to someday explore more of the ‘wild’ and less tourist-y places on the island when we return.

Standing in front of the beach in Oak Bluffs, before heading to dinner in Edgartown.

(Photo taken by Hunter on 35mm film)

Oak Bluffs

For our long weekend, we paid to bring a car over on the ferry into Oak Bluffs. This was super convenient for a longer stay, and allowed us to explore the island a lot and have flexibility to our plans. We stayed at a bed and breakfast right across from the beach on Oak Bluffs. Oak Bluffs is one of the biggest towns on the island, with a main street full of restaurants, bars, and shops. One place you’ll have to visit is Back Door Donuts, but make sure to get there early so that you have your pick of the best options. We ate at Lookout Tavern and enjoyed the food and the views immensely. A historic and iconic stop downtown is the Flying Horses Carousel, the oldest operating carousel in America. It was originally from Coney Island, and it features a challenge to grab a brass ring and win a free ride.

The two popular beaches in Oak Bluffs are Oak Bluffs Town Beach and Inkwell Beach. Across from the Town Beach is Ocean Park, an expansive green space with a gazebo, surrounded by beautiful homes. Oak Bluffs is also home to the ‘gingerbread houses’, originally a 19th century Methodist campground and now a collection of 300 summer cottages that provide the illusion of stepping into a neighborhood from a fairy tale. The open air tabernacle at the center is also impressive, and still houses public events and religious meetings. There is a museum that you can tour to see what the inside of one of these homes looks like. It is well worth at least walking around to see all of the unique homes and see some residents enjoying their beautiful porches.

I highly recommend a drive along the slim Beach Road between Oak Bluffs and Edgartown. This will take you over Jaws Bridge, where you will inevitably see people jumping into the water. The beaches along this stretch are crowded but beautiful.

Gingerbread houses in Oak Bluffs.

(Photo taken by Hunter on 35mm film)

Vineyard Haven

This summer, we took the ferry into Vineyard Haven and then took advantage of the public bus system to make our way around the island a bit. This is also a cute town on the island, with more restaurants and shops to peruse. We ate brunch at Sweet Bites when we arrived. We then worked through where to head first on the bus. The public transportation is cheap, often air conditioned, and pretty efficient. There are some routes that only run every hour, so you have to plan accordingly to give yourself enough time while also not doing too much waiting around. We encountered a mix of friendly and completely unfriendly people during this most recent day trip – not sure if that was the normal New England affectation or if it was pandemic induced stress, but the day certainly required a bit of patience. I thoroughly enjoyed seeing so much of the island from the bus, and loved the small town feel of the bus stopping at random locations along the road to pick up passersby.

Black Dog Campus features shopping, delicious food, and oceanside views. We ordered takeout from the Attic that we all enjoyed - quick turnaround, fresh ingredients that are worth the price. We also visited Island Alpaca Company which was fun and educational. And I had the best strawberry rhubarb pie of my life from Pie Chicks!

Tisbury

The West Tisbury Farmer’s Market is worth a trip as well. It is the oldest and largest farmer’s market on the island, “founded in 1934 by farmers in response to the Great Depression” (https://www.wtfmarket.org/about). We also visited the Scottish Bakehouse to buy some goodies during one of our drives across the island, and visited here multiple mornings when we were staying in Tisbury during our recent trip. Their breakfast sandwiches are so good.

We visited the Polly Hill Arboretum and absolutely adored this experience. There are a few different trails through either forest or fields, a wide variety of plants and trees, and some wildlife. The history of the buildings on the property and their continued use is also fascinating.

One of my new favorite spots is North Tisbury Farm Stand! We went back three times during our five day stay and had the freshest fruit and vegetables. They also have freshly baked goods delivered every morning around 8:30 am. I had a baguette from here that was perfection and some other pastries that were equally divine. The unassuming front of this building has roses creeping all along the doors and porch, and then you enter into a haven of curated local goods that will not disappoint.

On the deck at the Seafood Shanty in Edgartown.

(Photo taken by Hunter on 35mm film)

Edgartown

Edgartown is another large town on the island, and in my experience it is the more upscale location on the island. It is a beautiful place to wander. You can walk along the main downtown street to visit shops and restaurants. Even the government buildings, like the town hall and district court, are gorgeous. We also walked down the residential streets along the water, which featured stunning homes and gardens. We walked out to Edgartown Harbor Light, which is on a beach surrounded by water. We saw many yachts moored around the lighthouse. One day, we ate at the Seafood Shanty out on the upper deck. It offered views of Chappaquiddick, and great food and drinks. The Chappaquiddick car ferry is a truly one of a kind experience to watch in action. I definitely want to make it out there one day! One of the best and most indulgent meals we have ever had was at the Atlantic Fish & Chop House to celebrate our anniversary. We shared appetizers, and ate entrees and desserts accompanied by ice wine and dessert ciders. It was a lovely meal and one of the best experiences I’ve ever had.

We also went to South Beach one morning to enjoy some ocean time and relaxation.

View of the Chappaquiddick car ferry dock from the Seafood Shanty.

(Photo taken by Hunter on 35mm film)

Aquinnah

If you’re on the Vineyard, you absolutely have to make the trip out to Aquinnah to see the cliffs and visit the Gay Head Lighthouse. I still want to travel down to the beach below the trips, but the view from the top is stunning! You can see across the water to nearby islands on a clear day. We also paid to walk up the lighthouse when we first visited, which we enjoyed. During our day trip this past summer, we were all looking for a refreshment and a chance to sit down. We ordered drinks and some onion rings to sit at the Aquinnah Cliff Restaurant. It has a deck overlooking the water and the cliffs as well. There are shops with various local goods here as well.

During our most recent trip to Martha’s Vineyard, we walked down to the beach at the base of the cliffs. I can’t believe it took me so long to do this and I highly recommend you make the walk down while you’re at the cliffs! As long as your whole visit is under two hours, you should be able to stay in the same parking lot or you can move your car down to the beach parking lot. The beach is full of beautiful rocks, soft sand, and the cliffs themselves are made of the softest clay in beautiful spectrums of color. We were a large group and walked along the beach for quite a while - but did not realize that the end of this section is also a nude beach until after! There weren’t many people on the beach because the morning was quite overcast - but during the course of our walk, it cleared up and became another stunning sunny day on the island!

We also stopped at Orange Peel Bakery and got some goodies - but it’s on my bucket list to go back and get pizza from here on one of the days they make it!

At the Aquinnah Cliffs.

(Photo taken by Hunter on 35mm film)

There is so much to do and see on the island! There are a few popular ice cream shops, including Mad Martha’s. For all your tourist needs and goodies, visit Soft as a Grape or Black Dog. We also visited as many lighthouses on the island as we possibly could.

I also saw the Martha’s Vineyard airport for the first time recently. We drove through while on the bus, and it was by far the cutest airport I had ever seen and was so quintessential Martha’s Vineyard, with the Cape style signature shingle siding and white accents. Flights were recently announced from my town’s airport right to the Vineyard, so we’ll see if those are ever something we can afford or indulge in ;)

I look forward to expanding my knowledge about all things Martha’s Vineyard on my next trips – and I hope that this guide will help you on your own adventures!