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An Amateur's Guide to Martha's Vineyard

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Hob Knob Luxury Boutique Hotel, Martha's Vineyard, Edgartown

You might recall that it was my birthday last month? The hubs and I figured it was the perfect excuse for a weekend getaway. We chose to head to Martha's Vineyard for a few reasons: we wanted to do something relaxing but different from what we normally do. We also wanted somewhere that was close enough to drive to and since we'd only be there for a long weekend, it had to be worth it. I also have a not-so-secret obsession with New England and have had Martha's Vineyard on my bucket list for years.

It was our time.

Needless to say, we had a total and complete blast. Hopefully you were following the adventures on Instagram? To complete the journey, I decided I'd compile a list of things we really enjoyed doing on the Island, should you be thinking of heading over there on vacation and need to be pointed in the right direction.

Without further ado, here is my mini amateur guide to Martha's Vineyard. (Amateur because this was my first time there and it wasn't even peak season, which means that a few things were still closed, which makes me by no means an expert on the place and I'm certain that I'll be leaving out a ton of amazing things that I didn't get to do.)

Hob Knob Luxury Boutique Hotel, Martha's Vineyard, EdgartownMartha's Vineyard, Edgartown, New England, J Brand Jeans Houlihan, Soludos espadrilles

Where to Stay

I'm going to repeat what people recommended to me and say that you should most definitely stay in Edgartown. It truly epitomizes coastal New England charm. The architecture is what dreams are made of, the shopping is plentiful, the seafood is stunning and the activities are boundless.

We had the pleasure of staying at the Hob Knob Inn on Main street and I can't recommend it enough. We wanted something private that felt luxurious yet unpretentious. That's exactly what the Hob Knob is. The place is absolutely beautiful, their attention to detail was beyond, as was the level of service and friendliness of the staff. I wouldn't stay anywhere else if I went when I go back.


Martha's Vineyard, Edgartown, New EnglandHob Knob Luxury Boutique Hotel, Martha's Vineyard, EdgartownHob Knob Luxury Boutique Hotel, Martha's Vineyard, Edgartown, Happy Socks, Eberjey robe

What to Do

There really is no lack of things to do on the Island. Even though we were there a couple of weekends before the regular season started and not all businesses had opened yet, we were far from bored. Even if that meant chilling out on the Hob Knob's sprawling patio with a good book. As luck would have it, the Martha's Vineyard Wine Festival was happening while we were there and we spent an afternoon sampling delicious local fare and more importantly: really, really good wine. Tee hee.

Here were some super fun things we did that I would highly recommend:

- Bike rentals. Head to Wheel Happy in town and rent bikes for the day to explore around. Take the very short ferry ride over to Chappy Island to bike around uninterrupted by traffic. It's super pretty and so remote, you'll almost feel like you're in an episode of Lost. For real tho.

- Menemsha sunsets. Holy shit, I meannnn. We did this as many times as we could: drive over to the beach in Menemsha as the sun is going down, grab some rosé or champagne, and watch as the sun disappear into the water while parked cozily on a blanket. On of the best parts? The smell of the sea and the sound of the waves crashing on the beach.

- Gay Head Cliffs. Talk about an insane view. Getting up there is truly special, like you're stepping directly into a postcard. Warning: the wind can be quite intense - don't wear a hat!

Hob Knob Luxury Boutique Hotel, Martha's Vineyard, EdgartownHob Knob Luxury Boutique Hotel, Martha's Vineyard, Edgartown, Kaufman Mercantile bag, We Are Summer round beach towel


- Aquinnah. This up-island area is as remote as it is charming.

- Orange Peel Bakery. This place is a real trip and totally worth popping into. Be very attentive as you're driving past because it's a blink-and-you'll-miss-it spot on a sparse road. They make everything from scratch in their crazy brick wood fire oven that sits outside the tiny cabin where the bounty is sold. Speaking of sold, you basically walk in, put the money for what you take in a jar, and go on your merry way. Honor system (we don't see much of that in Brooklyn)! We had a nice chat with one of the owners, who told us all about their mantra. It's incredibly refreshing to meet great people who care about good things. Anyway, we left with the most amazing bread and yummy granola.

- Back door donuts. This place in the town of Oak Bluffs serves freshly baked donuts outside of a bakery's back door after midnight. Hot. Donuts. OMG. Get the apple fritter, that's their specialty. It'll blow your doors off. Pun inteded.

- Alley's General Store. This place is such a trip. You either feel like you've entered a time machine or a movie set. Or maybe a little bit of both. Knick knack fans, this one's for you.

- Get some fudge at Murdick's Fudge. So much variety you'll have a hard time choosing. Allow me to help you: the butter praline is the way to go.


Hob Knob Luxury Boutique Hotel, Martha's Vineyard, EdgartownHob Knob Luxury Boutique Hotel, Martha's Vineyard, Edgartown

Where to Eat

- Menemsha Fish Market. It's literally a shack and it's right on the beach. Get the lobster roll/soup special combo. Probably the most delicious clam chowder I've ever had in my life, no exaggeration. Eat it at their tiny counter or grab it to go and enjoy right on the beach. Bliss.

- Atria. This restaurant is right across the street from the Hob Knob and it was the bomb dot com. The regular restaurant on the main floor is a little bit more upscale and has a fine dining vibe, so request to be specifically seated in their basement, which they call the Brick Cellar Bar. You'll feel like you happened upon a perfectly art-directed, cozy old English manor. They have the most incredible selection of burgers, which is only offered downstairs (as if you needed another reason to not go with the fancy dining room). I highly recommend the Rip Off - that's the name of the burger - think Big Mac but made with quality ingredients. It's ridiculously off the hook. The service was also fantastic. Not only did they greet us at our table with bubbly (thank you to the best hubby in the world who mentioned my birthday when making the reservation), but our waiter was attentive and awesome in a cool friendly and super authentic way, as opposed to annoyingly formal.

- Wharf Pub. This completely unassuming bar totally surprised us in the best way possible. We were looking to get a lobster roll at the Seafood Shanty by the water in Edgartown but it hadn't yet opened for the season. We weren't in the mood for anything fancy for lunch, and we love a good chill pub, so we decided to grab two seats at the bar for a seafood feast that was pretty exceptional in both taste and simplicity. I still salivate over the fish and chips, clam chowder and cod cakes we had. I'd recommend the bar section as opposed to the dining room, but it's a matter of preference. Worth adding that service was so incredibly friendly and seamless. You can tell that this place is a riot at night.

Hob Knob Luxury Boutique Hotel, Martha's Vineyard, EdgartownMartha's Vineyard, Edgartown, New England, J Brand Jeans Houlihan, Soludos espadrilles

- Offshore Ale. Great bar with great food in Oak Bluffs. We had the lobster roll (duh). It was excellent and chock full of lobster meat, as well as accompanied by deliciously seasoned crispy homemade chips. Their portions are absolutely insane - saw other dishes go by and they were just as ginormous as our lobster rolls, if not more - so it'll be difficult to stop yourself from eating the entire thing. The place has kind of a barn atmosphere thanks to peanut shells discarded all over the floors from the baskets they hand every table upon arrival, and is super lively at night.

- Alchemy. This is more of a casual fine dining spot. Really delicious food.

- L'Étoile. Fine dining French restaurant. Really delicious but fancy AF, so know what you're getting yourself into! Definitely more of a special occasion kind of place.

Edgartown, Martha's Vineyard, New EnglandMartha's Vineyard Wine Festival, Edgartown New EnglandMartha's Vineyard, Edgartown, New England, J Brand Jeans Houlihan, Soludos espadrilles


There were other spots that we were really keen on trying, but unfortunately had yet to open for the season, such as the Outermost and the Seafood Shanty where we couldn't have the lobster rolls, which are both apparently lovely. Have you been to Martha's Vineyard before? Did I miss anything? Do you feel my list? Let me know in the comments!


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