Top Things to do in Martha’s Vineyard for First-Timers

Things to do in Martha’s Vineyard 

Reunited for a weekend in Martha’s Vineyard and it feels so good!

You may recall that Alex, Kristin and I haven’t been in the same place since our dive trip to Bonaire and subsequent R&R trip to Aruba in August 2015. Or perhaps you’re thinking… “You three are ALWAYS together!” Not so, grasshopper. Sure, I danced with Alex in Vegas for Bachelorette 2.0 a few weeks after our Caribbean adventure, and I’ve seen Kristin in the Bahamas for my magical beach wedding (lol), in Jacksonville and in Panama City Beach, but the trifecta has not been wholly reunited since last year. (Hilarious group texts don’t count.)

As we wound down last year’s beachy dive trip, we agreed that our next trifecta squad jaunt would take place upon Alex’s return from Koh Tao.

And here we are! The stars aligned in all of our schedules and after a quick stop on the way home from TBEX in Minneapolis (where I spoke about how to stay off the press trip blacklist) to empty my business casual wardrobe all over the floor (sorry, honey!) in exchange for appropriate New England attire, I was off to Boston to meet up with the gals.

Our first night as spent at Alex’s lil sis, Olivia’s apartment, just a few minutes from Boston Common.


We didn’t have long to wander the city. Bit of a bummer because I’ve only spent a day there in the past and it has so much to offer. We did get to eat at Red Lantern, an Asian fusion place with great ambiance.

Lobster fried rice? When in New England…


marthas vineyard

Early the next day we were scheduled to drive to Woods Hole to catch the ferry over to Martha’s Vineyard. Lucky for us, it just so happened to be National Doughnut Day, a ridiculous and welcome excuse to road trip while gorging on carbs from the famed Blackbird Doughnuts.


marthas vineyard

marthas vineyard

marthas vineyard

With Boston in the rear view, we made the easy journey over to Martha’s Vineyard – Oak Bluffs, to be exact. First impressions? It looked exactly how I expected it to look!

Dripping with adorable, preppy New England charm.




The Perfect Weekend in Martha’s Vineyard

Before visiting, my knowledge of Martha’s Vineyard was embarrassingly limited. It consisted of a hazy link to the Kennedy curse, Vineyard Vines lobster-embellished pants, and Jaws. You know, that feel-good film about a cuddly sea critter just mind his own business and flashing his million dollar smile to vacationers.


marthas vineyard shark

marthas vineyard shark

marthas vineyard shark

Though this summer blockbuster of epic proportions filmed on Martha’s Vineyard more than 40 years ago, the connection hasn’t lost its power over time. Not only are their little reminders scattered all over the island like a scavenger hunt for any true Carcharodon Carcharias-lover, but Jaws plays every Sunday at the movie theater in Edgartown. I’m crossing my fingers for a revived Jawsfest in the future.

Here’s to swimmin’ with bow-legged women.

While I think the Jaws connection is fabulous, others, namely my severely galeophobic friend Kristin, were more into other aspects of Martha’s Vineyard. As such, I quickly learned that there’s a lot more to the island shaped like Pharrell’s hat.

marthas vineyard

marthas vineyard

Marthas Vineyard

First things first – where to stay in Martha’s Vineyard?

I was fortunate enough to be an invited houseguest in one of a few hundred gingerbread cottages within the Martha’s Vineyard Camp Meeting Association. Located in the heart of Oak Bluffs, the MVCMA is the cutest little community I’ve ever seen. It dates back to the early 1800s when it developed as a religious camp for Methodists. What once was a mass of tents eventually lead to the building of more permanent structures. And, thus the colorful neighborhood of whimsical houses came to be.



marthas vineyard

In the summer months, the neighborhood is filled with residents and visitors, who come together for a weekly singalong in the central Tabernacle.

Shark memorabilia and a weekly singalong?! I may have found my place in this world, y’all.


Speaking of my place in this world: if Alex’s mom will have me, I intend to move into their pretty yellow cottage for the rest of time. Mmmmk. That might be overstaying my welcome, but guys, I had SUCH house envy visiting their place!

Alex’s mom – heretofore known as Kathryn, now that we’ve finally met in person – bought the historic house a few years ago. And to hear her tell it, it was a mega fixer-upper, filled with a mix of antiques and junk only a 100+-year-old house could possess.


Kathryn and team have spent the past few years revamping and restoring everything so now, in its present state, it’s one of the warmest, most welcoming cottages in the whole camp.

It’s seriously a Pinterest-lover’s dream come true, only get this – Kathryn doesn’t even use Pinterest. She got all these ideas from her own brain.






If you aren’t blessed with a cottage-owning squad member, you can reserve many of them during the busy summer months via the MCVMA website. But book early! Owners are only allowed to rent out the cottages to guests for a limited number of weeks each summer. This means that these babies are a hot commodity.

No room in the cottages? There are plenty of other options nearby, including the utterly precious and newly renovated Summercamp Hotel. It’s beautifully, brightly decorated. It’s a fun area and within walking distance to the ferry and all the shops and restaurants in Oak Bluffs. Convenient as can be, and there are board games and fun-tivities to be had around every corner.

Check here for prices & availability for the Summercamp Hotel


marthas vineyard

marthas vineyard

marthas vineyard

Another gorgeous place to stay on Martha’s Vineyard is the Harbor View Hotel in Edgartown. Built in 1891, this is an elegant property often used for weddings. It has a lovely view of the lighthouse and Chappaquiddick.

Check here for prices & availability




Where to Eat in Martha’s Vineyard

You know, if I’d just stop traveling to destinations with delicious food, I might actually be able to lose weight. Alas, girls’ weekend in Martha’s Vineyard is no time to stick to a diet. Beginning with the doughnut-related festivities in Boston, we continued on the island with some of Martha’s Vineyard’s hottest dining spots, including Red Cat Kitchen, Sharky’s Cantina, State Road, Art Cliff Diner and Slice of Life. There were dozens more restaurants we wanted to patronize. However, there is a limit to how much one can eat in a weekend, believe it or not!

My advice if you’re planning a visit to MV – map out where you want to eat well in advance, peruse Alex’s thorough recommendations and make reservations. Otherwise you may miss out on some of the tastiest experiences on the island.


More Things To Do in Martha’s Vineyard

1. Lobster ice cream (tried it, hated it)

I know, it doesn’t even sound appetizing. But when in Rome, do as the Romans do! Please tell me if this is something you actually enjoy…

2. The Edgartown Lighthouse

One of only five lighthouses on the island and a must when taking a trip to Martha’s Vineyard! 

3. Yoga at Yoga Barn

You know, to work off that bite of lobster ice cream!

4. Dancing with an interesting crowd at the Lamp Post


I can’t remember a time I had so many of my favorite things so naturally wrapped into one weekend. Jane Austen, sharks, lobster, yoga, home decor and two of my favorite people in the world. It was just the sort of escape I needed after several months of insanity.

As much as we did in a few short days, there’s still a ton we didn’t get to. This includes lobster rolls, Backdoor Donuts, bike rides, a singalong at the Tabernacle… Good thing, because I needed a quality excuse to show up at the cottage next summer. See you then, ladies!


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6 thoughts on “Top Things to do in Martha’s Vineyard for First-Timers”

  1. Absolutely loved reading and reliving this! Love your photos and descriptions of the campground. My fingers are crossed it isn’t your last trip to MV. We need to catch that community sing!

    And the post looks gorgeous — you’re doing great 🙂

  2. Loved the post! It took me back to my girls trip this past September when we all signed up (and finished!) the Zooma Women’s Half Marathon in Cape Cod. We then took the ferry over to MV and spent the day seeing the sights, eating, drinking and of course shopping at Vineyard Vines. I just loved the gingerbread charm!

  3. Angie, LOVED meeting you after hearing of your three musketeer adventures for so long. Thanks for all the love you’ve shot in the direction of my cottage. Definitely make sure you visit mid-week next time so you can experience the Wednesday night community sing, followed by a trip over to Backdoor Donuts.

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