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Chilmark: A Bucolic Up-Island Oasis
Martha's Vineyard Towns

Chilmark: A Bucolic Up-Island Oasis

Chilmark is a beauty of a town, home to seemingly endless rolling hills and rambling stone walls, as well as the rural fishing village of Menemsha.

Last Updated November 12, 2022

Chilmark is a beauty of a town, home to seemingly endless rolling hills and rambling stone walls, as well as the rural fishing village of Menemsha. Chilmark is quiet and tranquil, but it boasts a storied history. Chilmark was the first of the up-island towns to split from the original two towns of Martha's Vineyard, Edgartown and Tisbury; Chilmark was incorporated in 1694.

Interestingly Chilmark once had one of the highest instances of deafness in the world. At one point in the 1800s, it was said that one in every 25 people in Chilmark was deaf. Martha's Vineyard Sign Language was developed in the early 18th century and was used in daily life by both deaf and hearing people alike until as recently as the 1950s. The language served as a precursor to what we know of as American Sign Language today.

Today Chilmark is home to just over 1,200 residents, and is known for its stunning views and rural landscape. Many Chilmark homes are tucked away out of sight on multi-acre properties. Think more sprawling rustic estate, less contemporary beach houses. While other parts of the island are places to show off, Chilmark is a place to hideout. Many celebrities have homes in Chilmark and enjoy the anonymity of its untouched landscape.

Where to Stay in Chilmark

Chilmark is home to the Beach Plum Inn and Menemsha Inn & Cottages, both located atop a hill in the island's fishing village of Menemsha. These properties offer exceptional views at sunset and are among some of the only hotels in Chilmark. There's also the historic Captain Flanders House, a renovated farmhouse that takes pride in combining the modern comforts of today with the old-fashioned hospitality of days gone by.

When it comes to home rentals there are all sorts of vacation rentals available in Chilmark on both the North Shore and South Shore. From local realtors to Airbnb, Vrbo and more, there are everything from quaint country cottages to multimillion dollar mansions available for your Martha's Vineyard vacation.

Where to Eat in Chilmark

Like the other up-island towns of West Tisbury and Aquinnah, dining options are limited and spread out in Chilmark.That does not mean there is nothing to eat, but it doesn mean having a car is going to be the most convenient way to satisfy your hunger locally.

Chilmark is remote and places to eat are spread out. Having a car when visiting is recommended.

The Chilmark General Store

Chilmark is home to the legendary Chilmark General Store. Downtown at Beetlebung Corner, the town's unofficial town square, this general store offers a variety of pantry items, beach essentials, and a very extensive prepared and quick-service food options. If you are looking to grab something to take to the beach, look no further than Chilmark General Store, from salads and sandwiches, to homemade pizza, you are sure to find something at this up-island institution. Enjoying a slice of pizza on their porch is a rite of passage during your Vineyard vacation. Look out for unassuming celebrities who might be doing the same.

The Chilmark Tavern

Located next door to the Chilmark General Store is Chilmark Tavern, Chilmark's only full service restaurant. This local favorite is a BYOB establishment, however they are happy to mix you a cocktail with your own liquor, or provide a chilled glass for the beer you bring. This upscale eatery focuses on classic New England style dishes driven by local ingredients and inspiration.

Menemsha - Chilmark's Iconic Fishing Village

Lobster roll from Menemsha, Martha's Vineyard

Then there's Menemsha, the iconic fishing village and the ideal place to eat in Chilmark, assuming you like seafood. Menemsha is home to two fish markets that offer a full selection of fresh seafood, as well as freshly prepared seafood favorites like lobster rolls, clam chowder, shucked oysters, and more. Many people venture down to these markets in the late evening and enjoy some fresh seafood while they watch the legendary sunset at nearby Menemsha Public Beach.

Warning! Leave early if you're hoping to do that in the summer months as parking spots often fill up hours before the sun goes down.

Menemsha is also home to Menemsha Deli and Menemsha Galley for good quick eats. Menemsha Deli is open early and offers traditional deli and breakfast sandwiches. The Galley is open for lunch and dinner and has great hamburgers, sandwiches, and even soft-serve ice cream.

Shopping in Chilmark

Shopping opportunities in Chilmark are more limited than the bustling Main Streets of our down-island towns but its outposts are unique and beloved. The Chilmark General Store is an institution in its own right, offering groceries, provisions, and basic necessities. You'll find the freshest seafood around at Larsen's Fish Market and Menemsha Fish Market with local catches coming into the dock located right behind them daily.

Jewelry and Markets in Chilmark

Menemsha is also home to a handful of galleries and boutiques including the Ruel Gallery, home to the work of painter Colin Ruel and his talented jewelry designer wife Nettie Kent. The Chilmark Flea offers high-quality handmade items from Vineyard artists and craftsmen, antiques, imports, and vintage finds, on display at this open-air market at the Chilmark Community Church every Wednesday and Saturday in the summer season.

Local Produce and Farm Stands in Chilmark

For local produce and a quaint roadside farmstand experience head to North Tabor Farm, a small family farm that grows exquisite, nourishing food, much of what they grow as well as an expertly curated selection of beloved specialty items. There are also several other farm stands scattered throughout Chilmark, from rustic roadside honor boxes to high-end farm stands; so take the time to drive around and pop into these old-timey outposts. Chilmark is very rural and will require some driving time to get from place to place.

Things to Do

More than anything Chilmark is known for its scenic beauty, encompassing land and sea. When it comes to exploring the land we recommend taking a hike on the town's large network of trails. All of these trails can be found on the TrailsMV app. This app gives detailed information, maps, and directions to properties managed by The Trustees, The Land Bank, and Sheriff's Meadow.

Hiking trail in Chilmark, Massachusetts

Chilmark's hiking trails range from the highest point on the Island, Peaked Hill, to stunning ocean views at Menemsha Hills, and Great Rock Bite. From Menemsha Hills, you can take a long wooded walk down to the Brickyard, the ruins of an 1860's water-powered brickworks that provided bricks to construction projects in New York, Boston, and Newport.

Take a hike to the top of Peaked Hill and see if you can spot the fishing village of Menemsha from the highest point on the island.

Water Sports

If you're up for enjoying water sports, Chilmark's picturesque Quitsa Pond, Stonewall Pond, and Menemsha Harbor offer excellent places for stand-up paddleboarding, or kayaking. With protected clear water this is a great place to spend the day. Check out Book-A-Boat which offers rental options for Boston Whalers, skiffs, kayaks, canoes, sunfish, and more.

Photography Buffs

No trip to Chilmark is complete without catching a legendary sunset at Menemsha Public Beach. We've mentioned this a few times, and for good reason. It is a mecca for photographers and sunset aficionados. Don't be surprised if the whole beach starts clapping after a spectacular show. JAWS aficionados will likely recognize their surroundings while exploring Menemsha harbor, which was the filming location for Quint's (Robert Shaw) shack, and the last resting place for his boat Orca.

Cycling Chilmark

Avid cyclists will love the windy roads of Chilmark, though bikers beware there's limited shoulder area on Chilmark roads so ride with caution. We love to take the Bike Ferry from Menemsha to Lobsterville Beach in Aquinnah for more desirable cycling terrain. Bike miles of secluded road, or walk the secluded miles long Beach.

Warning! Bikes and cars share the roads up-island. Be sure to leave enough space for each other.

Chilmark Road Race

If you're more into running than cycling, the Chilmark Road Race, which has occurred since 1978, is a beautiful but oh-so-hilly course through Middle Road. Proceeds from the race are donated to the Town Affairs Council to assist in the operations of the Chilmark Community Center and make scholarships to year round residents possible.

Fishing in Chilmark

If you're into fishing, or if you want to just give it a try, Chilmark is the place to do it. Charter boats will take you from Menemsha, as well as many other places on the Island, for a day out on the water. You can also bring a rod down to the fishing pier or Menemsha jetty and try your luck from shore. Menemsha Texaco carries a small selection of fishing supplies if you forget a lure or a sinker. For the more serious striped bass fisherman, Chilmark holds some legendary secret honey holes, but we can't spill those tips here.

Family Friendly Fun

If you're looking for family-friendly fun check out what's happening at the Chilmark Community Center or nearby Chilmark Library. This quaint library is more than it seems with regular programming for all ages, and with its connection to a much larger network, you can find more than books at this library.

The Beaches of Chilmark, Martha's Vineyard

Menemsha Public Beach

Menemsha Public Beach in Chilmark, Martha's Vineyard

Menemsha Public Beach is located in the heart of the Island's historic fishing village, Menemsha. This beach is the most iconic place on the island to watch the sunset. Famous for its unobstructed west-facing views, people of all ages flock to this place before the sun goes down (and many of them give it a round of applause!).

Just steps from shopping, and fish markets serving fresh fish, and cooked meals, this beach is a great place to spend the whole day. This is one of the few beaches on the island that has public restrooms in the parking lot. Easily accessible to all ages and abilities, a visit to Menemsha is a must. Parking is limited in Menemsha, and can fill up quite quickly.

Lucy Vincent Beach

Lucy Vincent Beach

Some of Chilmark's most exceptional beaches are private, which means you cannot access them in the summer months without a town-issued beach pass, and this applies to Lucy Vincent Beach. If you are fortunate enough to be a town resident, or staying in a home with a beach pass, Lucy Vincent Beach is an iconic beach just past the Allen Farm on South Road.

Lucy Vincent is known for the dramatic sand and gravel formations that pepper its landscape, which has shifted dramatically over the years due to coastal erosion. Lucy Vincent Beach is a photographer's paradise and you'll find plenty of tripods set up at sunrise eager to catch the magic of the sky here in the early morning.

Visit Lucy Vincent on a crisp night and you'll be astounded by the sounds of waves and the beauty of the sea under the stars. You might even catch a glimpse of the sand sparkling!

There is a section of Lucy Vincent beach that is famously clothing-optional. Legend has it that the namesake Ms. Vincent herself wanted certain standards maintained on her beach, and nudity was not up to her standards. Some believe that the tradition of disrobing on this beach harkens back to the freewheeling attitude of those that visited the beach before it was public.

Squibnocket Beach

Squibnocket Beach is a Chilmark town beach located along the shore of Chilmark. This is a very popular place among surfers, and a legendary place for striped bass fishermen. Squibnocket Beach at high tide is limited to the space in front of the parking lot, though its reach expands when the tide falls, there are large rocks and cliffs on the up island side. Surrounded by private property and private beach access, this is the only access to this stretch of beach for miles.

Arriving to Chilmark via Plane

Chilmark is accessible for air travelers as it's a short 15-20 minute drive to the Martha's Vineyard Regional airport (MVY), the only airport on Martha's Vineyard. Traveling by plane is the fastest way to get to Martha's Vineyard and the views once you approach are simply majestic.

Given the seasonality of the island more flights are offered in the summer months, but depending on where you're arriving from there are daily year-round flights available:

  • Cape Air offers daily year-round flights from Boston and other major cities, plus additional seasonal service from New Bedford, Hyannis, and Nantucket in Massachusetts, as well as New York locations.
  • Major airlines including JetBlue, Delta and American Airlines offer seasonal service as well.
  • Private air charters are another option for flying into the Vineyard year-round.

The MVY airport is not located within walking distance to Martha's Vineyard attractions, though there is a restaurant, seafood market, and liquor store nearby, but outside of those offerings, you'll want to arrange for a car pick up or the bus to bring you to your ultimate destination.

Arriving to Chilmark via Ferry

Traveling by ferry is what most visitors to the island decide as their mode of transportation, and ferries arrive into Vineyard Haven year-round, as well as Oak Bluffs and Edgartown seasonally. Please note if you are arriving via ferry and plan to stay in Chilmark, you will need to arrange for a car pick up or the bus to bring you to your ultimate destination.

For passengers considering bringing their car on the island, note that the only car ferry is the Steamship Authority vessels departing from Woods Hole, MA. These are the only ferries that are capable of bringing your car to Martha's Vineyard, so when booking ferries, be mindful of this. Check out our full list of Martha's Vineyard ferries.

Explore Martha's Vineyard Towns

Martha's Vineyard towns each have their own unique character and charm. Explore around and get a taste of everything the Vineyard has to offer!