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Chilmark

Nestled on the enchanting Vineyard, Chilmark, MA, is a charming escape bursting with coastal beauty! Explore stunning cliffs, pristine beaches like Menemsha, and delightful art galleries. Embrace local seafood at cozy eateries and soak in breathtaking sunsets. Perfect for relaxation or adventure, Chilmark is a hidden gem inviting you to unwind and savor the island life!

From the Community

Recommendations

Landmark4.5/5

Chilmark Harbor Master

Nestled in picturesque Chilmark, the Harbor Master offers stunning coastal views and a gateway to serene beaches, making it a must-visit spot for those seeking a quintessential Martha's Vineyard experience.

Outdoor4.6/5

Menemsha Public Beach

Renowned for its stunning sunsets and tranquil atmosphere, Menemsha Public Beach in Chilmark offers visitors a picturesque escape with its sandy shores, vibrant fishing village charm, and breathtaking coastal views.

Outdoor4.4/5

Lucy Vincent Beach

Welcome to Lucy Vincent Beach, a hidden gem on Martha's Vineyard! This stunning beach charms with its soft sands, breathtaking cliffs, and crystal-clear waters. Grab your sunscreen and enjoy sunbathing, swimming, or beachcombing. Keep an eye out for dolphins frolicking nearby! With its laid-back vibe, it’s the perfect spot to unwind and soak in the island's natural beauty.

Outdoor4.6/5

Squibnocket Beach

Famed for its stunning cliffs and serene sands, Squibnocket Beach offers breathtaking ocean views and a peaceful retreat, making it a must-visit destination on Martha's Vineyard for nature lovers and beachgoers alike.

Outdoor4.8/5

Menemsha Hills

Welcome to Menemsha Hills in beautiful Chilmark, Massachusetts! This hidden gem boasts stunning hiking trails that wind through lush woodlands and lead you to breathtaking ocean views. Trek up the Trustees Ln for a chance to spot chirpy birds and maybe even some adorable seals! Don't forget your camera and a picnic, as this adventure is sure to make memories that'll last a lifetime. Come explore nature's playground!

Landmark4.8/5

The Brickyard

Nestled in Chilmark, Brick Yard is an iconic destination known for its stunning coastal views, tranquil beaches, and rich history, making it a perfect escape for nature lovers and those seeking serenity.

Outdoor4.8/5

Great Rock Bight Preserve

Nestled in Chilmark, Great Rock Bight Preserve offers stunning coastal views, rugged cliffs, and serene hiking trails, making it an iconic destination for nature lovers seeking tranquility and breathtaking scenery on Martha's Vineyard.

Eat4.8/5

The Grey Barn and Farm

Nestled in the charming Chilmark, The Grey Barn and Farm is a delightful slice of New England’s agricultural charm! This picturesque farm boasts fresh produce, artisanal cheeses, and a vibrant farmstand. Wander through lush fields, meet adorable farm animals, and revel in the rustic beauty. It’s the perfect spot for a whimsical adventure and a farm-fresh picnic!

Outdoor4.1/5

Nomans Land

Landmark4.4/5

Chilmark Community Center

Nestled in the scenic beauty of Chilmark, the Chilmark Community Center serves as a vibrant hub for local culture, hosting events and activities that celebrate the island’s rich heritage and foster community connections.

Culture4.5/5

Chilmark Free Public Library

Nestled in the scenic Chilmark, the Chilmark Free Public Library offers a cozy retreat with stunning views, unique architecture, and a vibrant collection, making it a must-visit for book lovers and nature enthusiasts alike.

Landmark4.6/5

Chilmark Flea Market

Chilmark Flea Market is a charming coastal gem, offering a delightful mix of antiques, handmade crafts, and local produce, all set against the picturesque backdrop of Martha's Vineyard. A must-visit for unique finds!

Outdoor5/5

Waskosims Rock Reservation

Nestled in Chilmark, Waskosims Rock Reservation offers breathtaking coastal views, serene walking trails, and unique geological features, making it a perfect escape for nature lovers and photographers alike.

Outdoor4.8/5

Tisbury Great Pond

Landmark4.8/5

Menemsha Beach

Known for its stunning sunsets and tranquil atmosphere, Menemsha Beach in Chilmark offers visitors a picturesque escape with soft sands, charming fishing shacks, and breathtaking views of the harbor.

Outdoor

Squibnocket Point

Renowned for its breathtaking coastal cliffs and stunning ocean views, Squibnocket Point offers a perfect blend of natural beauty and tranquility, making it an iconic destination for nature lovers and photographers alike.

Eat$$$$$4.4/5

Chilmark Tavern

Nestled in the picturesque Chilmark, Chilmark Tavern offers a cozy atmosphere and a menu brimming with fresh, local ingredients, making it a perfect spot to savor the flavors of Martha's Vineyard.

Eat$$$4.6/5

Larsen's Fish Market

Eat4.7/5

Menemsha Fish Market

Eat4.3/5

Chilmark General Store

Stays

Stay4.3/5

Menemsha Inn & Cottages

Stay4.1/5

Beach Plum Inn & Restauraunt

Stay3.9/5

The Captain R. Flanders House

The Captain R. Flanders House, a charming example of early 19th-century architecture in Chilmark, MA, captivates visitors with its rich history, rustic coastal charm, and scenic views of the picturesque surrounding landscapes.

Stay5/5

Nobnocket Boutique Inn

Nestled on Martha's Vineyard, Nobnocket Boutique Inn is a charming escape that feels like home! With cozy rooms, stunning gardens, and a delightful breakfast, it’s perfect for travelers seeking relaxation and local flavor. Adventure awaits at nearby beaches and shops, making this boutique gem a must-visit for an unforgettable getaway. Come for the tranquility, stay for the memories!

Things To Do
Provided by

5/5

Electric Bike Tours on Martha Vineyard

Explore the beauty of Martha's Vineyard on an electric bike tour designed just for you. It offers unique experiences tailored to your interests: secluded beaches, historic farms, the iconic Gingerbread Houses, and more. Let us take you there. Choose 4-6 hour private tour, where every detail is curated to ensure you see a few of the island's gems: lighthouses, Downtown Edgartown, Oak Bluffs, Chappaquiddick. Or call us and inquire about our 3-day Tour De L'ile for an in-depth adventure across the island's six towns. All tours include e-bike use, helmet, water, snacks, and admission to select attractions. - Explore top attractions like the Campground Cottages in Oak Bluffs and Chappaquiddick Island. - Private tours available for groups up to six riders, ensuring a personalized experience. If you have more riders, give us call a week in advance and we will try to accommodate you.

$200.00

5/5

Self Guided Walking Tour of Oak Bluffs Marthas Vineyard

Unearth the charm of Oak Bluffs on this self-guided walking tour, where the rich history and vibrant culture of this New England seaside town come alive. Wander among whimsical gingerbread cottages, enjoy stunning harbor views, and learn how this area evolved from a Methodist camp meeting site to a celebrated resort. This tour highlights the unique blend of architecture, community spirit, and African American heritage that defines Oak Bluffs, making it a delightful exploration of summer memories and local stories. — Discover the distinctive Victorian architecture and intricate cottages — Explore the historical significance of Oak Bluffs as a cultural hub — Enjoy scenic ocean views and shaded park paths during your stroll — Perfect for history buffs and those seeking a unique coastal experience

$9.99

4.9/5

3 h

#1 Best Martha's Vineyard Private Tours for up to 6 people

This private tour for up to 6ppl will introduce the history of our 6 unique towns! Oak Bluffs, a Victorian seaside, built around the Methodist campgrounds with its beautiful open air tabernacle and the Victorian gingerbread cottages once used for summer revival meetings,and the Flying Horse Carousel. Edgartown's stately white Greek Revival houses, The Old Whaling Church, the Edgartown Harbor Lighthouse, the historic Harborview Hotel. Vineyard Haven, the entry port to Martha’s Vineyard The scenic up-island country-side, historic farming towns of West Tisbury and Chilmark, a 15-min stop in Menemsha an Idyllic fishing The multi-colored clay cliffs of Aquinnah (Gay Head), with its impressive lighthouse where you will have an opportunity to get out take pictures and stretch your legs. island is so diverse, glimpse century old stone walls, The Atlantic shoreline, grazing livestock, rolling hills and historic homesteads. You well go over the bridge used in the filming of the movie Jaws!

$550.00

4.9/5

3 h

Private, Guided Sightseeing Tour of Marthas Vineyard Island(3hrs)

-Offering private tours of beautiful Marthas' Vineyard Island specifically for small groups of people (5 max) looking for a truly unique experience. -Relax and enjoy this narrated tour as we drive along the scenic coast, stop for photos, talk about famous people, learn about local history, all while passing through the 6 island towns. -For those travelers coming over for the day with limited time, who would like to see the whole island, this is the perfect tour.

$650.00

4.7/5

12 h

Boston: Martha's Vineyard ICONIC Small Group Day Escape w/Ferry

Leave Boston behind and set out on a full-day journey to Martha's Vineyard, one of New England's most beloved islands. This experience blends a scenic ferry crossing, historic seaside villages, and the laid-back charm of island life. Board the Island Queen ferry in Falmouth and cruise across Nantucket Sound to Oak Bluffs, where colorful gingerbread cottages surround the historic Tabernacle at the Martha's Vineyard Camp Meeting Association. Enjoy time to explore the island's most iconic spots, with an optional sightseeing bus tour covering the Flying Horses Carousel, the refined harbor town of Edgartown, Gay Head Light atop the dramatic Aquinnah cliffs, and Nobska Point Lighthouse. Return via the Steamship Authority ferry from Woods Hole, rounding out a full day of coastal views, ocean breezes, and authentic New England island character.

$108.00

4.6/5

3 h

Best of Martha's Vineyard 3 hour Full-Island Tour

Perfect tour to see all six towns on Martha's Vineyard in 3 hours, and to stop and get out to see the the beautiful seaport of Menemsha and the cliffs in Aquinnah. Customers will be engaged by great, "five star" local guides providing narration about the history, culture, celebrities, lighthouses, beaches, Jaws, gingerbread cottages, whaling captain's homes, and much more. Conducted in very nice, comfortable, air-conditioned, high top Ford Transit vans with large windows.

$65.00

4.6/5

3 h

#1 Best 3hr Martha's Vineyard shared Island Tour from Oak Bluffs

Experience our famous 3-hour full Island tour for a budget friendly rate! Our tour drivers - native Islanders & long-time "wash-a-shores" have years of tour driving experience and the best reviews to show it! This 3-hour tour will introduce you to our 100 square mile island by giving you the history, both past and present, of our 6 unique towns. In all, 2 ½ hours of the tour is narrated, and you'll have a stop at the beautiful Cliffs of Aquinnah. Top highlights on this tour include Oak Bluffs, Edgartown, Vineyard Haven, Aquinnah, West Tisbury, Chilmark, and Menemsha. So join us in our comfortable air-conditioned vans & get ready to make memories for a lifetime - your Martha's Vineyard tour! (Children under 10 excluded from this tour.)

$70.00

4.6/5

4 h

All New Shared Jaws tour Budget Friendly

What better way to experience Martha’s Vineyard – take a Jaws tour with us and you will have access to many of the films’ locations. You will hear many non-published stories about the filming, the actors, as well as being able to stop to take photos. The Jaws bridge is one of the top 5 attractions on the island. Jaws Factoids: - Although the movie is set in midsummer, producers began filming in early May 1974 to avoid an actors’ strike that was scheduled to begin July 1. - Jaws was marred with so many technical problems that the originally scheduled 55-65 day shoot ballooned into 159 days, not counting post-production. - Most highly anticipated movies were released around Christmastime, back then, but Spielberg took so long filming that the movie had a summer release date, which was traditionally reserved for low-end movies. - Townspeople of Martha’s Vineyard were paid $64 each for playing extras who ran across the beach and screamed during the shark attack scene.

$130.00

4.5/5

4 h

New Budget Friendly Shared 4 hour African American Heritage Tour

Experience the rich African American history of Martha’s Vineyard. Your experienced tour guide will talk about the graveyard and the formation of the NAACP on MV, as well as the connection between the Vineyard’s Grace Church and the one in Mississippi. At North Road, you will hear about Rebecca Amos, her daughter Nancy, and great grandson William Martin. In Menemsha, you’ll hear about the Wampanoag’s helping slaves escape. And in Edgartown you will hear more about Nancy and William Martin, and the Chappaquiddick Plantation. And finally, the Overton House, and its connection to the Civil Rights movement. Your African American Heritage tour includes driving by and/or stopping: • Cottager’s Corner • the Tivoli (which used to be Aunt Georgia’s) • Bradley Square Memorial Church • Bunny Cottage, • Dorothy West house • Coleman Corners • Shearer Cottage. It takes almost 2.5 hrs to drive the island. You will be stopping at several sites for pictures and to experience the rich history

$130.00

4.5/5

12 h

Boston to Martha's Vineyard Day Trip with Optional Island Tour

We are proud to offer Boston's ORIGINAL Martha's Vineyard Day trip. Since 2011 we have been Boston's #1 day trip service to the island. Our professional guides, approved Boston Hotel pickups and newer air-conditioned mini-coaches will help provide you with the personalized passenger experience that our guests truly deserve. Transportation to the island has never been this easy! You will also receive complimentary snacks, bottled water, island guidebooks and a discount card with some island perks! Once on the island, explore on your own or upgrade with our 3 hour fully narrated island tour. Let us help you Discover Martha's Vineyard!

$129.00

4.1/5

3 h

Martha Vineyard Bus Tour

Please Note: During the summer of 2026, our family experienced a devastating medical emergency involving multiple immediate family members. A small number of tours were canceled on very short notice while we handled those circumstances. We sincerely apologize to those affected and are deeply grateful for the kindness and understanding shown by so many guests during this incredibly difficult time. We are, the only ones have four stops to get off the bus. We also offer a lot of amenities that no other tour offers. The tours keep you fully engaged and all we require is for you to be curious! We will not disappoint, what makes us entirely different is that we have a screen at the front of the bus that shows what certain sites looked like in the days of yore. The All Island Bus Tour takes you on an adventure you will never forget. Capture the beautiful vistas, the quaint little cottages, the amazing clay cliffs and everything in between.

$75.00

3.2/5

Oak Bluffs, Martha's Vineyard Audio Tour

Knockabout Travel takes you to Martha's Vineyard, with this self-paced audio tour of the most popular town on the island. Discover the origin story of how Oak Bluffs developed from its humble beginnings as a religious camp into a summer destination for business moguls, celebrities, and US Presidents. On the tour, we discuss the development of the Martha's Vineyard Camp Meeting Association, home to the "campground" and the famed gingerbread cottages. Learn how the area around Ocean Park and Circuit Avenue was developed with tourism in mind, and how that conflicted with the original Methodist campers. Along the route, you will be introduced to some of the finer points and lesser-known history of the town, as well as places to grab lunch or a drink. The tour is GPS guided with turn-by-turn directions and audio tracks that play automatically at the right time and place so you're free to simply enjoy the tour.

$12.99

Discovering Oak Bluffs: A Self-Guided Audio Tour

Discover how a small religious summer camp transformed into one of Martha’s Vineyard’s most popular island destinations on this walking tour through the town of Oak Bluffs. Starting in Ocean Park, you’ll follow the coast to Inkwell Beach before heading into the heart of the town. Along the way, you’ll hear its history and find out what makes this island paradise so alluring to everyone from the rich and famous, to curious Cape Cod vacationers that come for a day. Around Trinity Park, you’ll see Martha’s Vineyard Camp Meeting Association, its cottage museum, and the Tabernacle in Oak Bluffs which is a place of worship. After heading down Circuit Avenue, where I’ll show you the town’s famous Flying Horses Carousel, our tour will come to an end at the harbor. Whether you’re on the island for only a day, or calling Martha’s Vineyard home for the season, this tour is for anyone who wants to dig into Oak Bluffs’ past and enjoy its present.

$11.99

5/5

2 h

Marthas Vineyard Luxury Tour (2hrs)

Offering private tours of beautiful Marthas' Vineyard Island specifically for small groups of people (5 max) looking for a truly unique experience. Relax and enjoy this narrated tour as we drive along the scenic coast, stop for photos, talk about famous people, learn about local history, all while passing through the 3 down-island towns. For those travelers coming over for the day with limited time, who would like to see the down Island towns, this is the perfect tour.

$550.00

5/5

4 h

Martha's Vineyard Private 4 hour Tour for groups up to 6 people

Enjoy your Martha's Vineyard Private 4-Hour Tour - experience the full Island tour with a few added stops. For example, you might include a stop for lunch, or at scenic areas along the way for some photos, maybe a stop by an art gallery, farm stand, or beach. • Include a stop (or two) to shop in Edgartown, Vineyard Haven • Is Chappaquiddick on your ‘bucket list”? We can definitely include this in your tour. (please note that, depending on traffic for the Chappy ferry, a Chappy tour may take about to 2 hours…and you always have the option to extend your tour beyond 4 hours)Cost of ferry for van & passengers not included. • Experience a Martha’s Vineyard sunset – possibilities include: Menemsha, Cliffs of Aquinnah, West Chop beach or East Chop Light! Let us help you Customize can make your tour and make it special just for you

$700.00

5/5

Boston Haunted History Self-Guided Walking Audio Tour

Traverse Boston’s oldest neighborhoods and hear about the lost souls still trapped within—from the poor, perpetually burning victims of a gas explosion in Boylston Station to a spectral woman in the Boston Common who tries to convince children to follow her into the dark. Walk through uneasy graveyards where the bodies have been moved, dug up, or lost altogether, and learn the stories of their unquiet dead. After booking, check your email/text to download the separate Audio Tour Guide App by Action while connected to WiFi or mobile data. Enter the password, download the tour, and enjoy it offline. Follow the audio instructions and route from the designated starting point. New, Lifetime access, no expiry. Use it anytime, on any trip, as many times as you want. This is not an entrance ticket to attractions along the route. Check opening hours before your visit.

$14.99

4.7/5

48 h

Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

Get the full Massachusetts experience with this combo of walking and driving tours around Boston! You’ll find ten tours in one app - all highly entertaining, thoroughly researched and prepared by local guides. Self-Guided Tours are: 1- Boston Freedom Trail (Walking) 2- Harvard Square (Walking) 3- Boston Ghost (Walking) 4- Salem Witch Trials (Walking) 5- Boston Harborwalk (Walking) 6- Plymouth (Walking) 7- Cape Cod & Provincetown (Driving) 8- Cape Ann (Driving) 9- Battle of Lexington (Driving) 10- Martha’s Vineyard (Driving) This self-guided tour allows you to explore Boston’s historic wonders with maximum flexibility and value. After booking, check your email/text to download the separate Audio Tour Guide App by Action while connected to WiFi or mobile data. Enter the password, download the tour, and enjoy it offline. Follow the audio instructions and route from the designated starting point. New, Lifetime access, no expiry. Use it anytime, on any trip, as many times as you want.

$49.99

4.5/5

13 h

Martha's Vineyard Day Trip with Optional Island Tour from Boston

We are a veteran owned coach service to Martha's Vineyard. Our ease of booking, convenient pickup and drop-off locations and comfortable, air-conditioned coach will provide you with a memorable experience. Enjoy a short ride from Boston to Woods Hole where you will board the Steamship Authority with no lines or waiting in a holding area. With us, you will have time to enjoy breakfast and coffee from a local cafe before boarding. As always, round-trip ferry tickets, snacks, water, island maps, discount food cards and commentary are all included. Island tour option; Unlike other tours, THIS IS NOT A SCHOOL BUS TOUR. A wonderful 3 hour, full island tour in one of our 14 passenger, air-conditioned, high-top vans is the best way to see the island. Tour goes through all 6 towns with stops along the way for pictures and restrooms. Our guides are the best in the business!

$130.00

4.2/5

Edgartown Martha’s Vineyard Self-Guided (GPS) Audio Walking Tour

Go at your own pace, anytime! It's your tour. On our historic walking tour of the Edgartown, you will see the iconic sights and secret gems including the whaling church, the oldest buildings, underground railroad locations, the Carnegie library, filming sights of Jaws, the lighthouse and much more. And I’ll tell you this town’s stories of the settlers, natives, whaling, ghosts, myths and legends, the Kennedy’s, it’s history and much more. Pro narration and production! Best deal in town :)

$9.75

3.9/5

Martha’s Vineyard Self-Guided Driving & Walking Audio Tour

Get ready to visit one of the greatest vacation spots in the USA, a favorite among celebrities and even presidents! Martha’s Vineyard is home to stunning beaches and coastline, picturesque little towns, and plenty of fun—but this GPS-guided driving tour with walking portions will also dig beneath the beautiful surface and into the island’s surprising history. Learn about the Wampanoag, the origin of the Vineyard’s famous “gingerbread houses,” and the lost language invented by the island’s residents! After booking, check your email/text to download the separate Audio Tour Guide App by Action while connected to WiFi or mobile data. Enter the password, download the tour, and enjoy it offline. Follow the audio instructions and route from the designated starting point. New, Lifetime access, no expiry. Use it anytime, on any trip, as many times as you want. This isn't an entrance ticket. Check opening hours before your visit.