Welcome to Chilmark
The rural feel and low-key community is a welcome change of pace.
Although this rustic fishing town was first settled in 1660 by James Allen, William Peabody, and Josiah Standish, it wasn’t officially incorporated until 1694, making it the first Vineyard town to separate from neighboring Tisbury and Edgartown, the two Vineyard originals. Now known for rolling hills, pastoral meadows, and pristine beaches that are mostly unchanged since those early settlers arrived, Chilmark offers a laid-back lifestyle and spectacular beauty.
The land’s wild, untouched quality may evoke images of early settler life, but the homes here are another story entirely. Often set on sprawling acreage and designed with every amenity in mind, the architecture ranges from quaint saltbox styles to modern farmhouse structures with floor-to-ceiling windows to take in every last inch of that unbelievable scenery.
What to Love
- Scenic beaches
- Laid-back charm
- Stunning views
- Tranquility and elegance
People and Lifestyle
A favorite among both young professionals and retirees, Chilmark has been named one of the best places to live in Massachusetts. The rural feel and low-key community is a welcome change of pace for those plagued by the stress of business or corporate life. A cherished respite for its highly successful, affluent residents, Chilmark has seen everyone from titans of industry to politicians lounge out on its remote beaches, their eyes closed, heads tilted back, relishing the feel of the salt air against their skin.
Dining, Entertainment and Shopping
Life in this serene setting may be quiet and peaceful, but make no mistake — Chilmark provides the best of the best when it comes to cuisine and shopping. Fill your kitchen with the bounty of Chilmark’s local farms and gardens at The Grey Barn and Farm, an organic, sustainable farm offering an incredible selection of farm-fresh cheeses, eggs, produce, and pastries. Hand-picked and brought immediately to the shop, these ingredients are the absolute height of freshness and quality.
Sit back and relax at the Chilmark General Store, an old-fashioned community market featuring island-grown produce, a charming covered porch, and rocking chairs. Get the freshest fish straight from the sea at the family-owned Menemsha Fish Market.
Life on the island may not require dress shoes or suits, but residents do indulge in the most luxurious fabrics and fashions. Relaxed summer wear is the specialty at Pandora's Box, a designer boutique offering jewelry, chic outfits for a night of fine dining, and that perfect bag you haven’t been able to find anywhere else.
Things to Do
Chilmark is a close-knit, affluent community, and residents enjoy organizing fundraisers and celebrations to support worthy causes. The Chilmark Road Race has been a town fixture since 1978 and is an important fundraiser for the Chilmark Community Center — not to mention one of the highlights of every Chilmark summer. The race is run along the scenic but very hilly Middle Road, and proceeds from the race are donated to assist the Chilmark Community Center and to create scholarships for year-round residents.
Celebrating diverse filmmakers and stories, The Martha's Vineyard Film Festival showcases the best in indie films and documentaries. Highlights include the drive-in, the Cinema Circus, and outdoor screenings. Stop by the iconic Chilmark Flea Market for antiques, imports, vintage finds, and handmade items from Vineyard artists and craftsmen. Supporting the worlds of dance, theater, and music, The Yard offers acclaimed performances and community programs to spark creativity and encourage a love of the arts.
Take in the stunning Menemsha sunset, watch the waves crash over the rocks at Squibnocket Beach (called Squibby for short), or grab your surfboard and head to Lucy Vincent Beach. Even if you don’t so much as dip a toe in the water, the incredible view of the clay cliffs is worth the trip.
Another scenic must-see is the Menemsha Hills, a protected nature reserve boasting an impressive lineup of special events, farmhouse dining, and scenic hiking trails.
Established in 1663, the illustrious Chilmark School specializes in multi-age classrooms, S.T.E.A.M., and a project-based environment for students in kindergarten through 5th grade.
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