Martha’s Vineyard

With summer in full force it was time to take a weekend trip to a classic New England destination: Martha’s Vineyard, or better known as simply, “the Vineyard” to locals. After coordinating with our summer trip friends, Emily and JC (Block Island in 2015!), we soon locked down a weekend. While we did not realize it at the time of booking, we later found out we were not the only ones with this great idea; the first family vacationed on the Vineyard during our time there.

Friday August 5th

While flights in the summer are easy to find, they can be quite pricey, so we decided to travel via ferry. This option is a quick and efficient means of transportation to get to the Vineyard. The SeaStreak ferry leaves the pier at East 35th street at 4:00pm on Friday and returns Sunday evening, leaving the Vineyard at 4:00pm. While the journey is just over five hours, the boat is enjoyable, and includes a cash-only bar for drinks and snacks.

We opted to bring our own snacks and alcohol (technically not allowed, but didn’t seem to be enforced) and passed the time with card games, books, and Opening Ceremony of the Olympics on one of the several TVs on board. The boat claimed to have Wi-Fi, however it never worked. Also, at $240 per person roundtrip, it can seem pricey but was more affordable than flying and less of a hassle than driving or taking the train. The ferry travels through the Long Island Sound before entering into waters of the Atlantic Ocean, at which time the ride can get very choppy. So if you get seasick this is probably not the option for you!

Martha’s Vineyard is not your typical small, New England island; it is quite larger than one might think. Measuring over 20 miles at its widest point, it is possible to explore a part of the island via bike. If you are looking to explore the entire island you will need a moped or car. We opted to forgo a car and booked a bed and breakfast in the main island town, Oak Bluffs, where the ferry drops off. As we were only going to be on the Vineyard for the weekend, renting bikes and using those as our primary means of transportation to get to the beach, etc. seemed to be the appropriate action.

Martha's Vineyard | Ocean Park

Ocean Park greets you off the dock and is a hub of activity.


Once arriving on the island we made the quick 10 minute walk to our bed and breakfast, Brady’s, to check in and drop luggage before heading out for dinner. From reading reviews of Brady’s online we knew it would be a great spot to set-up headquarters for two nights. Reviews of the B&B were all around good, however nothing to blow us out of the water, which is what we were expecting considering the steal we were paying ($200/night in the dead of summer). Upon arriving Brady greeted us and showed us around. He lives on the first floor and left the second floor to us (a total of four bedrooms and two bathrooms), which made it feel less like a typical B&B and more like staying at your distant great uncles for the weekend.

The house was quaint and definitely had a rustic feel. It was well maintained, and nearly every square inch of wall space happened to be covered with framed pictures, posters, etc. After settling in, Brady welcomed us back downstairs with a shot of whiskey to get the night started off right. He also started on one of many “Brady stories” we heard throughout the weekend (another thing we picked up on while reading reviews), which we enjoyed before finding a great place to cut in and excuse ourselves as our stomachs started growling.

Martha's Vineyard | Bradys NESW Bed & Breakfast

Bradys B&B – 10 minute walk from the ferry.

Martha's Vineyard | Brady's Interior

Four bedrooms, two baths, and more frames on the wall than we could count!

We walked back into town with a few options for dinner and saw Martha’s Vineyard Chowder Co., featuring plenty of seafood. The menu flaunted the “Best Chowder in New England” so we ordered a bowl to share. Wow! The menu didn’t lie, and we would highly suggest ordering a bowl for each person in the group. All of our plates were delicious, especially the local scallops, all complemented by the beer selection.

Looking for somewhere to grab a night cap, we walked down Circuit Avenue after hearing the sounds of a live band playing their hearts out. We quickly realized the music was coming from The Ritz, and paid the cover charge to join the party.

Martha's Vineyard | The Ritz

Lively music and a dancing crowd at The Ritz.

As the night was drawing to an end we decided to make our way back to the B&B and ended up walking right by Back Door Donuts. After realizing what it was, we hopped in line and each picked out a different, freshly made donut. We had read about this/were told about this before our trip, and it did not disappoint! Make sure you head for this back door when visiting.

Martha's Vineyard | Late Night Donuts @ Martha's Vineyard Gourmet Cafe' & Bakery

Late night lineup…for the donuts!

Martha's Vineyard | Late Night Snack @ Martha's Vineyard Gourmet Cafe' & Bakery

Garret opted for the strawberry filled donut, but Emily’s “Supreme” cake donut won by unanimous decision.

Saturday August 6th

Another thing we learned about Brady’s from the reviews is that the second “B” (breakfast) in Brady’s B&B was lacking, therefore we decided to pass up on his breakfast offer and head into town to find somewhere to eat. Quick research online led us to find a cute breakfast place in Edgartown, the next town south. First though, we needed to rent bikes in order to get to Edgartown. We walked to downtown Oak Bluffs and found a rental shop, King’s Rentals, with reasonable prices for a two day bike rental (see recommendation regarding King’s below). We hopped on the bikes and headed south for what we thought would be an easy, <30 minute ride to breakfast.

Martha's Vineyard | King's Rentals

Mopeds, bikes, and some suspect returns.

An hour later we finally made it to Edgartown. While the ride was relatively smooth, the road is right on the water, which created both a windy and slow ride. It was a beautiful route, but would suggest grabbing breakfast in Oak Bluffs before attempting to ride. By the time we walked around and found where we wanted to eat it was nearly noon. Luckily, breakfast-turned-lunch at The Wharf was delicious! This might sound weird, but they truly know how to fry seafood the right way (as in not overly crunchy/burnt like Long John Silvers). Everything, especially fish and chips, were amazing.

Fully refueled and restocked after The Wharf plus a stop at the liquor store, we rode a few miles to South Beach, where the afternoon was spent under the sun. The beach itself is the bare minimum, so make sure you pack snack and drinks. Important to note there are several port-a-potties and changing areas for public use.

Martha's Vineyard | South Beach

Hittin’ the dunes with JC.

Martha's Vineyard | Right Fork Diner

A diner with bi-planes on the way to South Beach.

Martha's Vineyard | Cheers!

Cheers to multi-tasking.

As the clouds started to roll in we headed back to civilization and stopped for a lobster roll at the Right Fork Diner on our way back to Edgartown. Unfortunately, the diner was already closed for the day. We made it back to Edgartown and couldn’t get the thought of lobster rolls out of our head, so we strolled along the water and spotted The Seafood Shanty. On their large second floor deck overlooking the water we enjoyed a seafood feast that hit the spot! An original plan of “just a quick snack”, since we had dinner reservations at the highly recommended Red Cat Kitchen, quickly turned into a full-on attack on the menu after we saw the dishes being served around us.

The seafood was complimented by delicious ice cream from nearby Scoop Shack, along with window browsing (definitely go beyond the window at Portobello Road). At this point it was late, and a storm was threatening to stop by, so we snagged a taxi (bikes strapped onto the back) which drove us back to Oak Bluffs just as a light summer rain hit the area. We enjoyed the rest of the evening on the wraparound porch at Bradys.

Martha's Vineyard | The Seafood Shanty in Edgartown

Fresh Lobsta’.

Martha's Vineyard | Scoop Shack

Grab a scoop at Scoop Shack.

Martha's Vineyard | Scoop Shack

Not just ice cream at Scoop Shack.

Martha's Vineyard | Brady @ Bradys

Brady, JC, and a hatful of stories.

Sunday August 7th

Sunday morning we found a close restaurant with good reviews and settled on breakfast at Linda Jean’s. The wait time was worth it, and the sausage, egg and cheese biscuit puts McDonald’s in its place.

Martha's Vineyard | B&B Lounging

Good morning from the balcony off the bedroom!

One piece of advice we received was to check out the gingerbread houses in Oak Bluffs, so after lunch we wandered around until we found ourselves surrounded by over 300 quaint, beautiful, miniature houses. It is a fascinating story of how they came to be, and very cool Oak Bluffs worked to preserve the area through the years.

Martha's Vineyard | Wesleyan Grove

Over 300 “gingerbread” houses confined in a small part of Oak Bluffs.

With the boat back to Manhattan not until 4pm, we had time to squeeze in some of our favorite summer vacation drinks – mudslides! We went to Nancy’s to try out their famous Dirty Banana. It was very delicious, especially when enjoyed on their second floor patio overlooking the many boats and yachts floating in the harbor.

Martha's Vineyard | Nancy's

We found the Society summer classic, mudslides, at Nancy’s.

Martha's Vineyard | Deck on Nancy's

Great views of the harbor from Nancy’s deck.

Martha's Vineyard | Nancy's Mudslides

People watchin’, boat watchin’, and mudslidin’.

Martha's Vineyard | Crew at Nancy's

A couple of Emilys and their guys.

After heading back to the B&B to pick up our bags and say goodbye to Brady we headed back into town on our bikes with all bags aboard. We were quite a hilarious site and even more so when Garret was “pulled over” by a police woman on a Segway who told him he needed to dismount. After telling the officer he was unable pull luggage plus a bike, she shook her head and said to not go the wrong way down one way streets.

Martha's Vineyard | Rolling Along

Return the bikes + get your luggage to the dock.

Check in for the bikes went from simple to quite an adventure, as Garret was accused of losing the key to our bike lock. We had kept the bike lock in Garret’s bike basket all weekend, with the key in place, while riding around, only removing it to lock our bikes up at each stop. A bike lock is designed to hold the key in place even while riding. It seemed very suspicious as soon as we turned our bikes in and began to walk away, we were loudly accused of losing the key and charged a $20 replacement fee. So if you do rent from King’s, just make sure you confirm your lock and key are turned in before turning your back. Or just don’t rent from King’s.

As we knew the boat had limited food we ordered pizzas to go from Giordino’s before hopping on the boat and making the trek back to Manhattan. Another great part of the Northeast explored!

(De)Parting Words of Advice:

  • The island is huge! Biking did the job for our two day trip but we aim to go back for a week and rent a jeep to fully explore.
  • Order seafood often, it is so fresh and delicious.
  • Because of its size there are things to do for everyone – bike around, shop in the towns, rent a jeep or moped, head for the beach, or post up and drink a mudslide.

Martha's Vineyard | Abandoned Movie Theater

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