100% Island Time: August in Martha’s Vineyard

The time has finally come to catch up on my black hole of content from August of 2016 to April of 2017! I can’t wait to turn my detailed notes and journals into blog posts from Canada, the United Kingdom, Hawaii, Thailand and Bali! But first, my final stop in the continental US, Martha’s Vineyard.

My apologies for any confusion with the timeline, and thanks for sticking with me!

Martha’s Vineyard has a reputation as a summer retreat for the East Coast elite — which is only partly accurate. First of all, you can visit Martha’s Vineyard on a budget, and in fact the island’s year-round community is decidedly salt-of-the-earth.

Also, you can’t really just show up any time the sun is shining and expect the true Martha’s Vineyard summer “scene.” The island actually has a fairly short true peak season that kicks off around Independence Day and wraps up around Labor Day. But there is nothing, nothing like a Martha’s Vineyard August.

I’ve been visiting Martha’s Vineyard since I first started forming memories, but my two-week trip in August of 2016 was the most action-packed that I’ve ever had. Come to the island in June and you’ll find empty beaches, traffic-free roads, empty tables at the hottest restaurants in town and more. Come in August, and you’ll have no such luxuries — but you’ll also literally be spoiled for choice when it comes to choosing how to spend your precious summer days and nights.

I landed off a shockingly affordable flight from Chicago (just $120 one-way with a connection in Boston — seriously unheard of for that time of year!) and pretty much collapsed from a long day of travel.

But the next evening, after a day at the Campmeeting Association’s Cottage Tour (post to come!) my mom and I kicked off our event calendar with an evening at the Martha’s Vineyard Film Festival Summer Series in Chilmark. Martha’s Vineyard has a pretty impressive cinema scene for such a small island thanks to the number of celebrities that love the island and the laid-back reception they can get here. Even Jake Gyllenhaal has done chilled-out meet and greets after opening-week screenings of his new movies!

At the Chilmark Summer Series, each screening is accompanied by dinner from a different island food truck, and this time we lucked out with Mangku Food Truck, who was serving up lemongrass pork, cabbage slaw, and a local egg over organic brown rice. Honestly, I was glad we ate first as the documentary we watched was pretty gut-wrenching: Trapped is a must-see for anyone concerned with reproductive rights in America. We were very moved by both the film and the discussion afterwards with both the President of the National Institute for Reproductive Health and one of the film’s main subjects, Dr. Willie Parker. A serious and tough but so important topic — both my mom and I went home and made donations as a result. The power of film is incredible!

The next day, we lightened things up a little with a twilight barnyard screening of Zootopia at Barnyard Movie Night at The FARM Institute. My mom’s fiancé Miller joined for this one and pointed out that we were indeed the only crew there without a kidlet under the age of ten, but I for one believe you’re never too old for movies in which small animated animals teach big life lessons. We brought beach chairs, blankets and snacks, and they projected the movie onto the side of a barn. How sweet! At a suggested donation of $10 per family, it’s a super affordable Vineyard night out.

Not long after, Ian arrived from Canada and after ten weeks apart he was a sight for sore eyes. He was also, unsurprisingly, thrilled by Miller’s purchase of an old beater Jeep Wrangler that he fixed up as a car for us to keep on the island year-round.

After a few days of beach hopping and lolling around the house (and one outdoor barnyard yoga class, because Martha’s Vineyard), it was time for a major date night. We spiff up pretty good for two kids who live in the Thai jungle!

I had made us a reservation at Down Island, a buzzed-about new restaurant in Oak Bluffs. With a five course tasting menu changing once a week, I’d been nervously refreshing their Instagram for ages hoping we’d both love what was being served (okay, it was really only me I was worrying about.)

I shouldn’t have worried. Our waiter graciously offered to swap the two dishes involving fish for a chicken and a vegetable option, and we marveled over each and every inventive course. At $59 — without adding on tax, gratuity, and booze — it’s not a meal we would do every day but I would love to return once a summer. If it’s good enough for the Obamas, who had bought out the restaurant a few nights prior, it’s good enough for us!

Down Island will absolutely be on my next Where To Eat in MV edition.

After dinner, we rushed upstairs — literally, Oak Bluffs is tiny — to the Martha’s Vineyard Comedy Festival at The Lampost. I love stand up and was so excited to get a night of it in on my favorite island! The Vineyard jokes were spot on and I think we pretty much burned off our dinner calories just laughing. 

We were also, sans exaggeration, the only white people in the room aside from the bartenders. Martha’s Vineyard, or more specifically Oak Bluffs, is notorious as the elite summer enclave for African Americans and other Americans of color — especially in August. We love living in such a diverse neighborhood on Martha’s Vineyard and getting to be a part of such a unique cultural destination in America.

I can be guilty of seeing the Vineyard as too much of a “home” destination and can put my head down and work from the time I wake up until the the time the sun goes down. My mom, luckily, is quite convincing at pulling me away from my laptop and herself and Miller and Ian away from home renovations for an hour of beach time a day.

It’s good for the soul — especially when we borrow the neighbor’s stand up paddleboard for a spin around the bay at State Beach.

The evening after the comedy festival was The Grand Illumination, but that’s so special it’s getting a post of its own! And the night after that — I told ya August is packed — Ian and I followed a long bike ride gathering info for my budget guide with an evening at Thursday Night Jazz at Featherstone. Ian is an enormous jazz fan, and I’ve long been wanting to catch a performance here, where you’re welcome to again, bring a beach chair and a blanket and a picnic of your own making.

At $10 a person, it can make for a pretty magical and affordable date night. We followed our wine and appetizers up with dinner at Brick Cellar Bar, another new restaurant for us. A friend who’s family visits Edgartown every summer had sung the praises of the restaurant’s amazing burgers and craft cocktails, and always eager for a new Edgartown find, we happily set off to try it. Tucked down in the basement below the much stuffier Atria restaurant, it was a hit. I’d go back!

The next day, the house popped off as the whole crew arrived for the weekend! My sister and two of our best family friends arrived to celebrate her birthday (a month late, natch) while she was in town for a political fundraiser. We kicked off their visit with yet another new restaurant, and one I’d been dying to try for years.

Lola’s is an absolute island institution serving up upscale yet casual, creole-infused soul food. Their Sunday Brunch is their most famous meal, but we were thrilled with their dinner menu and vowed to come back again for omelettes and oysters soon.

Then we were off to Ocean Park, where Oak Bluff’s beloved annual August fireworks were about to pop off. Our amazing neighbors had secured excellent edge-of-the-park seating for us to plop down our beach chairs (BYO beach chair and snack events are very popular on Martha’s Vineyard, clearly.)

The fireworks that followed were nothing short of fantastic, nor was the company we spent it with.

The next morning, while Olivia was hard at work setting up for an event that night, we were back in our favorite bay showing our guests Ashlee and Nina what the stand up paddle life is all about. Even my mom came out on a board!

Of course, I couldn’t resist getting a little yoga in.

We couldn’t linger at the beach too long — we had a fundraiser to attend. As many of you know, Olivia spent two years working on the Hillary Clinton campaign, and we were proud to attend many fundraisers and rallies by her side.

This was without question the most scenic and we were absolutely honored to hear Mrs. Clinton speak on issues close to all our hearts. My dad even flew in from California to be with us — it was a really special day.

While Olivia had planned to hang around the rest of the weekend, duty called, and she had to head off to another fundraiser that very same night! Guys, I don’t know if I’ve ever seen someone work so hard as that girl worked in the final year before the election. You think you were exhausted by the election near the end? Try the people who staffed them!

We were gutted to see her go as our time together that summer was scarce, but we happily took on the entertaining torch and after a morning at the beach shuffled off to one of my favorite island August events as a child, The Martha’s Vineyard Agricultural Fair.

Martha’s Vineyard is surprisingly agrarian, and this summer highlight truly shows off the best of it. I have such incredibly fond memories of this event as a kid and it had been years since I’d been back, so I was thrilled to return with not just both my parents but Ian as well to bore with childhood memories and gush over random jolts of déjà vu.

In addition to the usual 4H competitions and carnival rides, this particular fair features gorgeous island food, impressive works by local artists, and news and updates about the island’s efforts to go green, like the plastic bag ban that proudly passed in five out of the six island towns (and has since gone through in all six — woo hoo!)

That night, we rounded out the politically-minded week with a showing of Capital Steps, a musical theater satire group who was performing their recent album “What To Expect When You’re Electing.” Most of the performers have at one point or another worked on Capital Hill, and it shows! The whole thing reminded me of an intellectually-minded, long-form SNL skit. It was also my first time — that I can remember — checking out the Martha’s Vineyard Concert Series.

Whew! Can you believe we fit that all in to two short weeks — alongside a healthy heaping of work days? I loved this Vineyard August so fiercely I vowed to make it back again for another soon. While I adore the shoulder seasons of early-June and mid-September and the peace and solitude they come with, there is something truly magical about the buzz and the chaos and culture and crowds of a Vineyard August that reminds me why this little island means so much to so many people.

I’m grateful it’s been such a big part of my past, and will continue to be such a big part of my future.

Stay tuned for a Vineyard cottage update, and then onward to Newfoundland!

If you’d like to see Martha’s Vineyard through my eyes, my family’s historic Oak Bluffs gingerbread cottage is available for weekly rentals. We renovated each room by hand and I’d love to share its magic with you!

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