Kathleen’s Guide to Martha’s Vineyard

Edgartown Light

Pretty Edgartown, Menemsha’s real fishing village, rural Chilmark, Oak Bluffs’ Victorian Cottages and all in between- if you know me, you know I love Martha’s Vineyard. My family and I try and spend two weeks each summer on this island off Cape Cod, Massachusetts. Although this year’s vacation was a bit different than summer’s past, we still had an amazing time. Having just returned earlier this month, I wanted to share my guide to the island, including spots that I’ve been visiting for years and new places that I discovered this time around. 

The great thing about the island is it is super lowkey. Nobody cares about what designer-label shoes or sunglasses you are wearing. It is truly a spot that is about flip flops and a relaxed, but still stylish, way of life. 

First, the basics: To get to there, you take either a plane or ferry. There are hotels and inns and resorts of all kinds but we prefer a house rental which is easily arranged by the week, month, or entire summer. I am partial to renting in West Tisbury because we like to get beach passes for, and frequent, Lambert’s Cove Beach, a bay beach only available to town residents and renters. The sand is super soft, more like the Caribbean than New England, and the water is a bit warmer- perfect for little ones and people like me who prefer a hot summer to a cool one. My favorite part is that upon arriving at the beach, there is a quarter-mile walk through a tunnel of trees that takes you to the dune. As soon as you hit the top, you see the sky, the water, and the whole beach opens up. That moment is when our vacation really starts!

For house rentals, Coldwell Banker has plenty of listings in Vineyard Haven, Oak Bluffs and Edgartown. I also love Tea Lane Associates as they offer homes that are considered “up island” where we like to stay. Sand Piper Rentals and Martha’s Vineyard Vacation Rentals also have great brokers who really know the island and they’re great at helping you find slightly more nuanced properties. 

The Sweet Life

If you’re not ready for a house, Winnetu and the Harborview Hotel are resorts that cater to families and multiple generations. The Hob Knob Inn has both rooms and rental cottages and is walking distance from everything in Edgartown. For a more relaxed vibe, The Beach Plum Inn is sweet, a short bike ride to Menemsha beach where watching a sunset will truly take your breath away, and they offer passes to Lucy Vincent beach - one of the most coveted spots on the island. If you’re anticipating wanting to meet friends in for the day, The Mansion House Spa and Inn is super well-situated in Vineyard Haven where one of the island’s ferry docks is located. In Oak Bluffs, where the other ferry dock comes in, Summercamp Hotel is a modern vibe in a very historic place. 

While on the island, a car is really helpful, allowing you to easily discover all there is to offer across the six main towns. You’ll find plenty of identity on Martha’s Vineyard, due in large part to the fact that there are a ton of building restrictions to ensure the character of the island is preserved. 

When dining out, State Road is an absolute must for dinner. It is one of the best places to eat on the island and is open year around. Among the Flowers Cafe, which is in Edgartown, is the perfect spot for lunch. It is lowkey, the food is always delicious, and the outdoor patio is scenic. The Net Result is amazing for fried clams and steamed lobster. We bring dinner back to the house so we can indulge comfortably without the guilt of having to prepare the meal. A tip? They ship! If I need a winter fix, I can always get them. For a special evening, we also love The Sweet Life in Oak Bluffs and their patio garden is a special little spot.

Cheeses from The Grey Barn and Farm

Like most people, one of my favorite things about a vacation is the indulgences, and there are plenty to be had on Martha’s Vineyard. 

We visit Back Door Donuts at least once a summer. The bakery is open daily, but Backdoor Donuts is only open starting at 7 p.m. each evening. I try and get there at 6:45 p.m. to beat the three-block line. This trip, I discovered a chocolate company called Salt Rock Chocolate Company  The chocolate is old school, very delicious, and is only sold at the West Tisbury farmer’s market on Wednesdays and Saturday. Two young women started the company in 2019. They knew the owners of Chilmark Chocolates, which has closed, and they resurrected the original recipes - they are worth the calories. Pie is very popular on Martha’s Vineyard. I always make sure to visit Pie Chicks when on the island. It is hard to beat a double crust. This time of year, peach everything reigns supreme.

Shopping local while on the island should be a priority. Martha's Vineyard is rural and a good amount of the land is used for farming. My absolute favorite is The Grey Barn and Farm. They make the best cheese on the planet and their English muffins are second to none. Yes, there are places to get it off-island but there’s something magical when digging into a sumptuous round of their “Eidolon” while watching a sky transition from a late afternoon haze into a dreamy twilight when the fireflies make themselves known. Tea Lane Farm offers the loveliest assortment of flowers on the island, hands down. Morning Glory Farm and North Tabor Farm are other must-visit farms. Morning glory’s chocolate chip cookies are a rare find but super yummy and their fresh corn is pure summer.  Do stop and buy the baby arugula from North Tabor’s road stand if you’re up-island. Just bring a few dollars since they still use an honor-system.

Bowls from the Chappaquiddick Wood Company

On non-beach days, I love to either go for a hike, spend the day shopping or hit up an art gallery. My favorite hikes are Felix Neck Wildlife Preserve and Cedar Tree Neck Sanctuary. Both are stunningly beautiful and a fun way to try work off all of the aforementioned treats. Granary Gallery is amazing for both local and notable art and the staff are perfectly content to let you freely browse but are ready to answer questions when they arise.

For shopping, I always visit NOCHI, Rags  and CB Stark for clothing, jewelry and accessories. For home goods, I love Tracker Home Décor. This trip, I came back with some amazing ideas and pieces that I can’t wait to start using: Bowls from Chappaquiddick Wood Company, Tableware from Up-Island Pottery, counter stools for future use from Marshall Farm Woodworks and a pretty laundry or storage basket from Island Alpaca.

If your trip allows for a full daytrip, you must drive to Aquinnah which is on the far western end of the island. You will see the historic lighthouse and should walk down the dunes to the beach. The view is something special and reminds me of a moody English beach scene. Chappaquiddick is also a must-see. For a full surf-beach day, Long Point beach is perfect: it is less populated than some of the other public beaches and also has an adjacent swimming pond- a good spot for those with younger kids or when you just want to laze on a beach raft. A little indulgence that does not make a lot of sense, but I do anyway - I like an early evening drive up to West Chop to see some of the older and more historic summer homes on the island. There’s a private club up that way which makes me smile when I see the glow of lamplight in their shingle style clubhouse’s dining room windows - I'm a sucker for the gilded age and this little corner of the island. If any of you reading this ever buy a house up that way, please give me a shot at designing one! 

These are just a few of the highlights of this not - so-little island. For those of you who have been, I’d love to know what I missed and where should I make sure I visit next time. For those who haven’t been, I hope this convinces you to visit - just leave the designer bags at home and I hope to see you on the ferry!