The Laid-Back Charm and Hidden Gems on Martha’s Vineyard

The family text thread blows up with non-negotiables as we plan our summer visit to Martha’s Vineyard:

“Back Door Donuts!”

“South Beach!”

“Farmers Market!”

“Mad Martha’s Ice Cream!”

It’s hard to fit in all our favorites.

You’ve probably heard about all the famous politicians and celebrities who have houses on Martha’s Vineyard – the Kennedys, the Clintons, the Obamas, Spike Lee, Joni Mitchell, and David Letterman, to name a few.

However, as someone who as been going to the island for over 30 years, its reputation as an exclusive summer resort for the wealthy is only half the picture.

A seaside dock area featuring wooden walkways, a prominent American flag, and colorful nautical flags. Various buildings with blue awnings are visible, along with individuals walking and enjoying the outdoors on a sunny day.
The dock in Falmouth, Cape Cod. Board here for the ferry, The Island Queen, to get to Martha’s Vineyard

There’s a laid-back quaintness to the island that’s hard to describe. Even when the island is in full swing—from late June through Labor Day—you can find a quiet spot to bike or read a book.

You’re more apt to park next to a beat-up Jeep than a Mercedes or encounter a makeshift farm stand with an honor-system money tin and bunches of freshly picked flowers than a shop selling designer duds.

A grassy coastal landscape with a wooden signpost in the foreground, a small pond in the middle, and blue sky above.
Biking on Edgartown Bay Road

Locals may feel differently but Martha’s Vineyard remains refreshingly unchanged year after year. My husband’s family has been coming to Martha’s Vineyard since 1962, and the summer apartment they rented back then is still going strong! Many of the businesses have been around for decades and when one closes, the locals mourn.

A calm beach scene with golden sand, gentle waves, and a bright sun in the clear blue sky. A person is lounging on a chair near the shoreline.
South Beach, Edgartown

Edgartown

Our family house is near Edgartown, where classic colonial and neo-gothic architecture from the 18th century mix with art galleries and shops to explore.

A white colonial-style house featuring black shutters, a welcoming front porch with steps, and an American flag displayed. The house is surrounded by lush greenery and flower pots, with a tree partially visible on the right.
Quaint Edgartown Streets are perfect for wandering

We like to walk to town and grab a clam chowder at the Quarterdeck food shack and meander over to the big dock where my husband fished as a kid. It’s fun to watch the five minute ferry go back and forth to Chappaquidick Island.

A ferry named 'On Time II' is approaching a dock with a 'Ferry Caution Crossing' sign. In the foreground, a travel mug sits on a post draped with an orange cloth that reads 'Travel Freely'.
Taking the ferry to Chappaquidick is a fun outing
A weathered wooden door with various signs indicating different beach locations, including 'South Beach,' 'Chappy,' and 'Amity Island.' A white shirt hangs on the door, along with colorful jackets visible in the background.
Shops in Edgartown
A night scene featuring a bright moon illuminating a landscape with lush greenery and flowering plants, alongside a sign that reads 'Harbor View.'

One night, we eat at the Harbor View Hotel, a five star luxury resort with views of the lighthouse.

A cup of light purple ice cream with a white spoon, placed on a textured surface.

After dinner, we walk to Mad Martha’s Ice Cream. I opt for my usual blueberry ice cream (despite the usual calls and urging for me to try something new). No way! It’s the best in the world.

West Tisbury

The sun is shining the morning after we arrive, so we head “up-island” to grab sandwiches at 7a Foods and have an impromptu picnic at the Field Gallery among the sculptures on the lawn.

Outdoor sculpture garden featuring white sculptures and a gallery building with colorful artwork on the walls
The Field Gallery in West Tisbury

Then it’s off to Menemsha to get clam chowder from the fish market to eat with fresh swordfish for dinner that night which will include a thorough discussion about said clam chowder, is it the best, where is the best on the island, how does it rate with Larson’s or Edgartown Seafood Market…lol….

Exterior of Menemsha Fish Market featuring blue trim and a wooden sign, with people sitting outside and nearby tables.

Preservation is at the heart of Martha’s Vineyard

Much of the island has been preserved in its natural state, thanks to the work of the Martha’s Vineyard Land Bank, Sheriff’s Meadow Foundation, and the Trustees of Reservations. These organizations preserve land for public use, allowing wildlife to flourish. We’ve become avid birders, and during our trip, we saw flocks of geese flying overhead, a gaggle of wild turkeys ushering their young across the road and an osprey guarding her nest. We also saw wild deer, ducks, and horseshoe crabs roaming in the shallows at the beach. Those things are huge!

Wild turkeys

Aquinnah

While we do have our perennial favorites, we seem to always find something new to do. The “big deal” this summer is the recently formed Squibnocket Pond Reservation, a 330-acre property formerly owned by Jackie Onassis now open to the public in Aquinnah. Scoring one of their 10 parking spots at the reservation is nearly impossible. So, my husband and I decide to bike there from Aquinnah Beach which is a couple of miles away.

Map and informational sign for Squibnocket Pond Reservation South, including trail options, access points, and details about the collaboration between Sheriff’s Meadow Foundation and Martha’s Vineyard Land Bank.

Following the windswept road above the cliffs, with the ocean stretching on our right, its a relaxing and beautiful ride.

A serene landscape featuring tall grass in the foreground, leading to a calm body of water surrounded by lush greenery and distant dunes under a clear blue sky.

When we arrive at the reservation, we check in with a friendly attendant at the booth who shows us where to park our bikes. We hike down to the water along a series of trails built to help keep the forest in its pristine state.

Martha’s Vineyard new preserve

After about a mile, we emerge on a cliff over the beach. We pause in the listening to the surf and seagulls occassional squacks. I imagine little Caroline and John Kennedy building sandcastles here when they were children.

A person walking along a wooden boardwalk through lush green vegetation under a blue sky.

After our three-mile hike and five-mile bike ride, we’re exhausted, so we hit the Aquinnah beach. It’s one of the most stunning places in the world. Multicolored cliffs look down on us as we splash in the surf and take in the scenery.

A beach access point sign for Moshup Beach with a pathway leading to the beach. Nearby, there are beach chairs, umbrellas, bags, and a bench surrounded by greenery.
A sandy beach with colorful clay cliffs in the background, featuring various earth tones and green vegetation on top.

Chilmark

On Saturday, we take a field trip with my brother-in-law. He brings us to the flea market and farmers market before we stop at Chilmark Pottery to pick up a soap dish.

Housed in a weathered barn, Chilmark Pottery has been around since 1982 and is run by veteran potter Geoffrey Borr. Inside, you’ll find him and his apprentices hard at work, shaping pieces on their wheels as you shop.

A variety of ceramic pottery and blue-glazed vases displayed on tables in an art studio or shop, featuring a large statue with a hat in the center.
A scenic rocky beach with smooth pebbles and large boulders, set against a backdrop of a blue sky with fluffy clouds and a green hillside.
Hiking to Great Rock Bight in Chilmark

Oak Bluffs

This year, we go see the Indigo Girls perform at the Tabernacle, an open-air event space in Oak Bluffs. The Tabernacle’s roots reach back to the religious revival movement that took place on the island in the 1850s. we enjoy a beautiful night of live music then weave our way through the historic district of gingerbread cottages to Back Door Donuts to get a piping hot apple fritter.

A group of people waiting in line outside a small shop at night, with various items displayed for sale, and a signboard visible.
Back Door Donuts in Oak Bluffs

Vineyard Haven

In Vineyard Haven, we eat at Salvatore’s one night. I’ve been home for three weeks and I can’t stop thinking of their linguini and clams!!!

Vineyard Haven is full of unique shops and restaurants. I like to head to LeRoux at Home to pick up gifts for the house, while Adam heads to the Bunch of Grapes Bookstore. We meet up for lunch at the Black Dog Bakery overlooking the water. Don’t leave without buying some classic Black Dog gear, which is instantly recognizable and beloved worldwide.

A black travel mug with a silver lid, featuring the logo of 'The Black Dog Tavern Co.' on its front, placed on a countertop next to a coffee machine.

While biking on our last day, I finally spot the elusive llamas on the lawn of the Boch property, a massive waterfront estate on Katama Road. They are quite famous and beloved by all who pass by. Even though I’ve seen them year after year, I still can’t resist stopping and snapping another picture! After all, its a tradition.

A llama resting under a tree on green grass, with a picturesque house and water in the background.
Llama sighting on Katama Road

Contemplating a summer vacation? Martha’s Vineyard has six unique towns, miles of beach and offers an endless basket of fun and delights for families and couples alike! Reach out to book.

Lillian Martin is a Senior Travel Advisor at Reece Worldwide Travel. To book your next trip, click here.

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