A Weekend in Martha’s Vineyard

Although Martha’s Vineyard is only a short ferry ride from the mainland, the pace and feel of the island is worlds away. My family and I recently spent a few days on the Vineyard for a getaway. Traveling in April, we risked rainy weather. Luckily though, on our three days stay on the island we had perfect weather.

Leaving from Woods Hole on the Steamship Authority boat, we made sure to book our car reservation weeks in advance. Having been to Martha’s Vineyard many times before, I knew for our crew (including my two sons) a car would be a needed amenity. If you don’t want to pay for the extra cost of the car, Martha’s Vineyard has a transit system that is efficient and cost-effective.

During our first day, we visited with friends at their house in Edgartown. We were also able to stop at Edgartown Books, a fine village bookstore where we purchased Goodnight Martha’s Vineyard to add to their “Goodnight Books” collection. After dinner at their house, Dairy Queen was in order for dessert. It was the only ice cream place open in Edgartown!

 Harbor View Hotel

The grand dame of hotels in Martha’s Vineyard is the Harbor View Hotel in Edgartown. Since travel has been on hold during the Covid pandemic, we decided to splurge and book this wonderful hotel for two nights. The Harbor View is located less than a mile from downtown Edgartown and is located across the street from Lighthouse Beach. 

Our room was absolutely perfect. It was spacious, with two king-sized beds, a porch, and a window seat in front of a picture window. Quite honestly this was the most comfortable bed and pillows that I’ve ever slept on. The hotel itself has an expansive wraparound porch with rockers to sit on, soaking in the view of the water beyond.

On the second day, we got a decently early start but spent over an hour exploring Lighthouse Beach, right across from the hotel. A meandering path through beach plum bushes leads out to a lighthouse, picturesque in black and white on a peninsula jutting out into the harbor. The kids all enjoyed romping all around the base of the lighthouse and exploring the nooks and crannies of the beach. One highlight was seeing the seagulls smash shellfish onto the lighthouse’s cement platform to access their next meal. Lighthouse Beach is magical and just a few steps away from the hotel!

Island Alpaca

Finally on the road, one of our first stops was Island Alpaca. The kids were able to get up close and personal to a number of these fuzzy animals. They also enjoyed picking out a stuffed animal alpaca to take home with them. 

A Geography Lesson about Martha’s Vineyard

After that, we drove “up island.” Martha’s Vineyard consists of a few distinct towns. Vineyard Haven is the primary landing place for ferries arriving from Woods Hole and New Bedford. Vineyard Haven is a nice mix of a main street with quaint shops, along with essentials such as a grocery store, gas stations, and restaurants. Oak Bluffs is another one of the three main towns. This has a summery feel of candy stores and t-shirt shops. With the Flying Horses Carousel, I would say that Oak Bluffs is the most popular for kids. Oak Bluffs also is the site of the gingerbread cottages. Built for a Methodist Camp Meeting in the 1800s, these colorful beauties are now a symbol of the whole island.

Edgartown is a gorgeous former whaling town. Its downtown is bathed in white paint with stately former captains’ homes some of which have been turned into inns. Of course, the Vineyard is known for its beaches such as South Beach in Edgartown and State Beach between Oak Bluffs and Edgartown. 

“Up Island” are the smaller towns including Aquinnah, Chilmark, and West Tisbury. Aquinnah is historically the home of the Wampanoag tribe and was, until somewhat recently, known as Gay Head. In Chilmark, the village of Menemsha has a handful of seafood shacks and is picture-postcard perfect. West Tisbury is more agrarian in nature is home to Alley’s General Store and a popular farmer’s market. To make things more confusing, there is also a town of Tisbury whose main village is Vineyard Haven which is described above.

Alley’s General Store

As I always want to take advantage of my surroundings in full, I wanted to make sure to go Up Island, especially since we had a car. The first stop was Alley’s General Store. This homey store would not feel out of place in northern New England! Grab a few groceries, some Vineyard t-shirts, and some toys here. My kids walked away with a bubble gun and a Care Bear.

Gay Head Cliffs

Driving all the way to the farthest point of the western side of the island, we reached Gay Head. The brick lighthouse gives it away that you are close. I’ve been here a few times but its majesty is unrivaled. Unfortunately, both kids slept through this portion of the ride, so my wife and I had to alternate visits to the cliffs. Parking at the end of the road, walk through the small village of shops for the best viewing area of the cliffs. The views are dramatic, as the surf meets the sand with rising clay cliffs protruding toward the sky.

Menemsha Fish Market

Back on the road, we had to drive three sides of Menemsha Pond to get to the village of Menemsha in Chilmark. There is also a small ferry here too for a more direct trip. Most of the restaurants that I had read about in Menemsha such as Larsen’s and Home Port were either closed for the season or closed for good. The only game in town was Menemsha Fish Market which, other than selling fish, is a seafood stand. With both kids still asleep, we ordered two lobster rolls for ourselves. They woke up in just enough time to watch us eat them next to Menemsha Beach. These were hot lobster rolls! The meat was delicious, the bun perfectly grilled with a generous amount of butter complementing the lobster. 

Heading back, we drove through Vineyard Haven and Oak Bluffs before heading back to the hotel.

The Wharf

After a few hours of lounging around and playing catch outside at the Harbor View, we chose to eat at the Wharf in Edgartown. The Wharf is a classic family restaurant and pub. With a dark interior and an extensive bar, it really feels cozy and would be perfect in wintertime. The menu had something for everyone, including chicken fingers for the kids and a seafood and pasta dish for me. 

Murdick’s Fudge

Trying to satiate our sweet tooth, we had to stop at Murdick’s Fudge which is close by to The Wharf in Edgartown. We picked a piece of chocolate and a piece of chocolate peanut butter to take with us.

Mocha Mott’s

After checking out of our hotel, we had a few hours to spend before heading back to the ferry in Vineyard Haven. Oak Bluffs was our destination. Walking along Circuit Avenue which is the main commercial drag in the town, we grabbed coffee and breakfast at Mocha Mott’s. Given its name, my wife and I split an iced mocha and I had a satisfying Morning Glory muffin. The kids both had cookies and proceeded to smear chocolate all over themselves.

Martha’s Vineyard Camp Meeting

The majority of our time was spent walking around the side lanes and alleys of the Martha’s Vineyard Camp Meeting Association homes. These gingerbread cottages are all unique. Painted in bright colors, no two look alike. As part of the Second Great Awakening in the 1800s, camp meetings for revival events took place all over the country. Cottage groves were built for housing, but these in Oak Bluffs have to be the most impressive. In the center of the community is a stage that is still used today. My kids enjoyed running around the green area. After expending a bit of energy, it was time to head back into the car toward Vineyard Haven.

Leaving Martha’s Vineyard

When leaving the island, my older son, looking downtrodden, proclaimed “I’ll miss Martha’s Vineyard.” Both boys had such a good time that they can’t wait to go back! Although the ferry is only 45 minutes away from my house and only a 45-minute ride to the island, it is an adventure. The boat ride alone intrigued the kids. Although I have been to the island many times, it was spectacular to see it through their eyes. We all want to return soon!