After a few days in Edgartown, driving “up island” towards Chilmark, I finally understood all the fuss about Martha’s Vineyard. The southwestern half of the island is less populated, more rural with rolling hills, stonewalls, farms and general stores. Turn a corner and you’d swear you’re in the English countryside. And the beaches - the reason that brought me to the Vineyard in the first place - are wilder with dramatic cliffs, rock outcroppings and fewer crowds: absolutely beautiful. Edgartown was a lovely first date, but the villages of West Tisbury, Chilmark and Aquinnah…well they were keepers.
It’s B.Y.O.B. in Chilmark as it’s a dry town… stock up on wine for your stay at MV Wine and Spirits by the airport. The staff is super friendly, knowledgeable and they have a large selection.
When renting a house…visit Beetlebung Farm for fresh produce, eggs and meats. It’s charmingly unmanned, pick what you want, write it down on the yellow pad and leave your money in the tin box.
Everyone claps when the sun goes down in Menemsha. An alternative to dinner is to head down to the beach, bring a bottle of Rose, get some lobsters and watch the sunset on the beach. (Or head to a late dinner after) Don’t think of driving as parking is impossible, instead take the path from the Beach Plum.
Way to go…book a ticket on the frequent ferries from Hyannis, (car reservations must be made well in advance) or avoid the summer traffic to the Cape and head to Quonset Point in Rhode Island to board the boat to Oaks Bluffs, an hour and a half fast ferry.
Stay: The Beach Plum Inn is sweet with just 5 rooms in the main house and 5 cottages scattered over its seven acres. It’s all lush gardens and ocean views of Menemsha Harbor with comfortable, beachy décor and a well-regarded farm to table restaurant that draws crowds for sunset dinners. The biggest bonus: the inn provides parking and walk on passes to both Lucy Vincent and Squibnocket beaches, two of the island's best beaches, private for residents of Chilmark. (Next door, Beach Plum’s sister property, the Menemsha Inn, is larger, more rustic and works well for families with larger cottages.)
On the Way: Driving from the ferry, the airport, or Edgartown, stop for breakfast in West Tisbury at 7a Foods. Order one of their tasty egg sandwiches on a homemade biscuit to eat on the porch with the morning bikers. Get a hippie cookie to enjoy later in the day and their iced coffee, made with a blend of Cocoa Hazelnut from Java Tree. Starting at 11:15 am, 7a starts selling their gourmet sandwiches and salads, perfect for a picnic hamper at the beach. (Vegetarians will be happy ordering the Shitake Umami Tsunami.)
Don’t Miss: Right next door to 7a, Alleys’ General Store has been serving the Vineyard since 1858; browse the aisles for a hit of nostalgia.
Farmers Market: On Wednesdays and Saturdays don’t miss the Farmers Market, held from 9-12, showcasing the goods from more than 40 farmers and purveyors from across the island.
Lunch: After checking into Beach Plum, it’s just a scenic, short walk down a woody path to the beach at Menemsha, a public beach known as the premier spot for sunset on the island. Wander around the working fishing harbor, the colorful fishing boats and shacks present endless photo ops. There is nothing more quintessential New England than eating a lobster on the docks at Larsen’s Fish Market or a basket of fried clams or shrimps at The Bite. Don’t forget to get extra napkins!
Beach: Load up on beach chairs and umbrellas at the inn and spend the rest of the afternoon at Lucy Vincent Beach--it doesn’t get much better. Take a walk down the beach and don’t be surprised when you get to the stretch of beach that’s clothing optional. Walk back along the clay bluffs admiring the rock formations below.
Dinner: State Road is one of those restaurants that you want to order everything on the menu—and you can’t go wrong—it is a delicious meal, from start to finish, right down to the excellent wines served by the glass.
Provisions: Have breakfast at Beach Plum or head to the Chilmark General Store and eat on the porch. Get some sandwiches and snacks to take to the beach. Buy a few of the 1 lb. bags of Chilmark Coffee Company, made on the island, to bring home.
To the Lighthouse: It’s a beautiful drive to Aquinnah, formerly called Gay Head, to visit the historic lighthouse and the Gay Head Cliffs on the westernmost point of the island. The light was dark for the last few months, as the lighthouse was carefully moved back 120 feet due to eroding cliffs. Climb the small hill past the shops of the Wampanoag Indians for incredible views of the cliffs and ocean below.
Back to the Beach: Another day, another unique beach—that’s what makes Martha’s Vineyard special. Go early to get a spot at the small parking lot of Moshup Beach. It’s a nice 10-minute walk down to the beach. This was my favorite beach; the multi colored cliffs a stunning backdrop, changing colors with the light. It’s also beautiful in the late afternoon. If you want to visit another beach venture to Squibnocket where the surfers hang out.
Dinner: It’s Chef Chris Fischers’ second season at the helm of the restaurant at the Beach Plum, with much of the produce coming from his nearby family’s Beetlebung Farm. At dusk the lawn starts filling with couples sipping wine, children playing ball or chasing the roaming chickens and wild turkeys; all getting ready to watch the day fade away and dine on the seasonal farm to table menu. Or head to Chilmark Tavern, Jenna’s Sprafkin’s casual American bistro, featuring a seasonal, creative menu using mostly local products. Highly recommended!
Don’t Miss: Before returning home, have breakfast at the Art Cliff Diner. Go early to avoid a long wait, it’s popular for a reason—you’ll understand after your meal of spicy chicken hash and eggs, breakfast tacos or delicious fresh made scones or waffles.