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Wednesday, September 21, 2022

Chilmark , Martha’s Vineyard, 02535

Chilmark is a rural town located on the western side of Martha’s Vineyard known to the locals as “up-Island”. The English-speaking community in Chilmark dates back to the 1600s, with its original Wampanoag residents dating back many generations further. Today this quaint town is home to roughly 1200 residents, with numerous farms and hiking trails, and few commercial businesses, Chilmark still maintains the agricultural feel it has had for hundreds of years. 

Downtown Chilmark is a very small village located at the corners of South Road, Middle Rd, and Menemsha Crossroad, known as “Beetlebung Corner”. Though the town center is small, there are a number of exceptional offerings here. Chilmark General Store is an institution, with a section dedicated to groceries, beach staples, and some household items, it lives up to its “general store” name, but the real attraction is the epic food offerings. Freshly baked pizza, breakfast bites, baked goods, pantry staples, and everything you could need for a beach picnic make this outpost an up-island gem. Chilmark Tavern is the premier dining establishment in Chilmark, featuring indoor and outdoor seating, locally sourced thoughtful food, and classic Vineyard vibes. Make your reservations ahead of time as it’s a coveted spot given the town’s limited formal dining options. For those looking to imbibe, note that Chilmark is a “dry town” meaning you can’t purchase alcohol but Chilmark Tavern does operate a BYO (bring your own!) policy which enables diners to enjoy their favorite beverage while dining.

Home to two working dairies, vegetable, and animal farms, Chilmark is loaded with options for

locally-sourced ingredients. Mermaid Farm and Grey Barn Farm both offer locally-produced

cheese of exceptional quality. Mermaid Farm is still an ‘honor box-style’ farm stand on Middle

Road offering vegetables, raw milk, yogurt, cheeses, flours, flowers, and more! Grey Barn is a

more modern farmstand offering award-winning cheeses, vegetables, baked goods, home

goods, and surprisingly more. Beetelbung Farm, The Garden Farm, North Tabor Farm,

Milkweed Farm, and more all offer exceptional locally-grown vegetables at farm stands

throughout Chilmark. Spend a pleasurable and explorative day driving the quiet country roads of Chilmark, hopping from farm-to-farm to appreciate their beautiful landscapes and gorgeous

locally-grown goods.

Flanked by the ocean on two sides, Chilmark is home to a number of seaside activities that draw tourists and residents from around the world. Hiking the many trails in Chilmark is a great way to get a lay of the land. With deep woody trails, long walks to epic ocean vistas, and hikes through old farmland, there is a trail for every comfort level. Popular hikes include Menemsha Hills Reservation and Great Rock Bight Preserve. If you’re traveling with kids don’t miss the Island Folk Pottery Sculpture Trails, a fairytale walk through the woods of Chilmark embellished with sculptures and enchantments at every turn. Information about the many hiking trails of Martha’s Vineyard can be found on the TrailsMV app. This app has maps, information, and even GPS directions to hundreds of miles of hiking trails, managed by stewards of the Island’s conservation properties including the Trustees, Sheriff’s Meadow, and the Land Bank. 

Many visitors come to the Island for the beaches, and the beaches of Chilmark are home to some of the most storied and secluded stretches of sand on the Island. Lucy Vincent Beach and Squibnocket Beaches are the most coveted and both town beaches require a resident permit to visit in the summer months. These beaches are both on the south shore of the island and offer exceptional south-facing views of the seemingly endless Atlantic Ocean. 

On the north shore of Chilmark, you will find Menemsha, the Island’s working fishing village, which you may just recognize from the movie JAWS. Menemsha town beach is open to the public, and staying for sunset is an absolute must. It’s common practice to hear rounds of applause after a classic Menemsha sunset. This is a family-friendly beach, just steps from the parking lot with public facilities. With two fish markets serving fresh and prepared seafood largely stocked by the boats docked behind them, art galleries, shops, casual takeout restaurants, and a gas station, Menemsha is a quaint seaside New England Fishing village where time seems to standstill. The whole family will enjoy a perfect Vineyard day from sun up to sun down there, and generations of summer visitors make it an annual event to do just that. 

Menemsha not only faces the ocean, but is located at the entrance to Quitsa Pond, a large saltwater inlet that is a great place for kayaking, stand-up paddleboarding, or small boats. On windy days, you’ll see kite surfers riding the water in the pond. 

When it comes to real estate, Chilmark has some of the most secluded properties on the island. Celebrities and high profile visitors often prefer the privacy and low profile Chilmark offers. There are a handful of rustic inns and bed and breakfasts in Chilmark including the Beach Plum Inn and the Captain Flanders House, known for their expertise in hosting weddings, but the rental properties here are without question some of the finest retreats you will find. 


Chilmark is most easily explored by car, but the Vineyard Transit Authority (VTA) has buses that run regularly down all of the main traffic ways. The bus can get you to hiking trails, the village of Menemsha, and downtown Chilmark. Biking in Chilmark offers some of the hilliest terrain on-Island though avid cyclists rejoice in the challenge.  Some of the hiking trails are bike-friendly too but note there are no bike paths in Chilmark, so be prepared to share the road.  

If you’re looking for a taste of relaxation, natural beauty, and old-world charm Chilmark is the place to go when visiting Martha’s Vineyard

Funded, in part, by the Massachusetts Office of Travel and Tourism.

More Posts and  Videos About Chilmark

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