Another week, another trip to a fabled New England destination! And for good reason – Martha’s Vineyard is filled with breathtaking island charm, from the stark cliffs of Aquinnah to the quaint cottages of Oak Bluffs to the stately streets of Edgartown. Wherever you go, you’re surrounded by heart-stopping views of the Atlantic and stunning, sweeping fields – often filled with farm animals. Just a quick 45-minute ferry from Cape Cod, it’s well-worth the journey from the mainland to experience all that the island has to offer, and I’m here to help you plan the perfect trip!
Where to Stay
Each area of the Vineyard has its own charm, but if you’re looking to be at the heart of a quintessential New England town with all of the shopping, exploring, and dining you can imagine, my recommendation would be to stay in or around Edgartown. There are plenty of hotels and Airbnbs in the area to choose from, and having done both myself, you really can’t go wrong either way.
I recently enjoyed an off-season weekend trip to the island, and I would be remiss not to share the wonderful experience I had staying at one hotel in particular. Located just ten minutes from Edgartown while having the feel of a secluded oceanfront estate, Winnetu Oceanside Resort truly has it all. The property is complete with an expansive lawn, a hot tub and pool, tennis courts, and a private path to South Beach. And there’s more than enough activities to keep anyone busy, from yoga on the lawn to tennis to a game room. To add to the convenience, the Winnetu provides an hourly shuttle AND a boat service to get you to Edgartown in no time. The rooms are luxurious and our stay was filled with smiles, room upgrades, free champagne and more. If you’re looking for an elegant experience with five-star service, housekeeping, and dining, I couldn’t recommend a better place.
What to Do
It doesn’t take much to have a perfect day on the Vineyard. A simple beach day could suffice, or a day of shopping in town. But that’s not all, folks! The island is larger than you might think, with plenty of room to explore and some of the best meals you may ever experience. See below for a more comprehensive list of all the best things to do, see, and best of all eat on Martha’s Vineyard!
Activities:
- The obvious choice is to spend the day at the beach during the warm months of the year. My personal favorite is South Beach, but there are truly no wrong choices. You can even let the air out of your tires and drive on at Norton Point for an added adventure.
- You can also spend hours wandering the streets of Edgartown, admiring the homes, stopping in countless shops and galleries, and of course, eating and drinking to your hearts’ desire. My favorite stores are SALTE and SLATE, and keep reading for a few of my favorite restaurant recs.
- Take the ferry over to Chappy for the day to explore, hit the beach, walk the trails, and even visit the Mytoi gardens.
- Jump off the Jaws bridge – this one is pretty self explanatory. Just watch out for sharks! 😉
- Take a trip to Oak Bluffs to wander around the gingerbread houses, do a little shopping and, most importantly, go to Back Door Donuts.
- Visit Morning Glory farm to experience the cutest farmstand filled with flowers, produce, treats, coffee, and the best banana bread you’ve ever tasted.
- Explore Vineyard Haven and its many shops, galleries, and cafes located along yet another picturesque harbor.
- For the outdoor adventurer, there are many biking and hiking trails to get the heart rate pumping while you explore to your hearts’ desire, including Great Rock Bight Preserve and Menemsha Hills Reservation.
- Drive out to Aquinnah to watch a sunset from the cliffs and you won’t be disappointed. Bonus points if you pack a picnic for dinner.
For a Cup of Coffee:
- Espresso Love for a classic brewed blend – best enjoyed with a breakfast sandwich on the side.
- Toccopuro for a delicious iced latte.
- Rosewater for a gourmet coffee or latte in a cozy, upscale setting. The vibes, dare I say, are immaculate, and the coffee is even better.
For a Beverage (or three):
- Port Hunter is the go-to destination for craft cocktails, complete with live music and a shuffleboard table that can provide hours of entertainment. I went here for four days straight during my last visit and it truly became my favorite place.
- The Newes for a casual cozy pub vibe in an elevated setting.
- Lookout Tavern in Oaks Bluffs to enjoy beers or cocktails in a lowkey setting with a beautiful ocean view.
- Bad Martha’s is a staple Vineyard brewery with a quaint patio for all the best beer to be enjoyed.
- The Wharf for a lively night cap in a dive bar setting.
For a Bite to Eat:
- Breakfast:
- Behind the Bookstore for the cutest outdoor brunch spot nestled in the trees behind – you guessed it – Edgartown Books. Their yogurt bowl is one of the best I’ve ever had and the shakshuka is in a league of its own.
- Katama Kitchen for a diner experience located on an airfield. You can watch the planes take off while you enjoy your omelet.
- Waterside Market for a delicious, classic breakfast in a quaint cafe setting. I am still dreaming about their french toast.
- Back Door Donuts for the most delicious donuts you’ve ever tasted. Enough said.
- Lunch:
- The Seafood Shanty for a casual (but delicious) ocean-front meal with the self-proclaimed biggest and best lobster roll on the island. I’d have to agree.
- Morning Glory Farm to experience the cutest farmstand you’ll ever see complete with a food truck offering quick bites and sandwiches.
- Rockfish for an upscale pub vibe with an excellent bloody mary, chowder, and lobster roll – what more could you ask for?
- Dinner:
- The Atlantic Fish & Chophouse offers oceanfront dining at its finest. The interior is sleek with just the right amount of nautical touches, complete with an unbeatable view overlooking the harbor. Known for its exceptional service and five-star food, this is one of the most coveted reservations on the island for locals and guests, and for good reason.
- Alchemy is an elegant bistro with a menu teeming with seafood and steak – and of course, specialty cocktails. Their menu is refreshed seasonally, and their dishes are filled with unique local flavors.
- 19 Raw for arguably the best seafood selection the island has to offer. The interior is small but sophisticated, and this is one case where size does not matter. They have a robust raw bar and seasonal seafood specials, plus plenty of options from the mainland and a plethora of gourmet side dishes. I cannot recommend this spot enough.
Whether you’re hoping to find a peaceful staycation, a scenic adventure, or a destination for upscale dining, Martha’s Vineyard is a truly magical place with a little bit of everything for everyone. It’s hard not to be won over by the island’s charm. Hopefully this guide is helpful in planning your new favorite New England trip, and until then, happy Fall! ☼
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