Martha’s Vineyard, MA City Guide

by Sabrina Smelko


Ever since she can remember, Sarah Waldman has visited Martha’s Vineyard in the summer. She has watched the island ebb and flow for 30 years, and together with her young family, took the plunge and moved there three years ago. Sarah is a food writer who just celebrated the publishing of her first book, Little Bites by Roost Publishing, and is already working on her second. Her husband Nick is a designer who is slowly renovating their 1924 cottage.

It didn’t take Sarah and her family long to fall in love with the island’s tight-knit community, laid-back lifestyle, and beautiful landscape. As a mom to two young boys, Sarah values the adventurous spirit of the island (think year-round surfing, fishing, hiking, and pond skating), the focus on local food, and the various entertainment options, from outdoor concerts to film festivals. Today, Sarah shows us that there is “more to Martha’s Vineyard than fancy homes and presidents,” as she takes us through some of her family’s favorite spots off the beaten path. –Sabrina



Airbnb & HomeAway (all Island) For larger parties and those traveling with children, a private rental house can be ideal. Both Airbnb and HomeAway have a variety of rental options across the island.

The Beach Plum Inn (Menemsha, Chilmark) is a special occasion destination with rooms, cottages, and private homes available for rent. Amenities include bike and kayak rentals, access to Chilmark’s Lucy Vincent and Menemsha beaches, tennis courts, and complimentary homemade breakfast. You can even gather eggs from the inn’s chickens.

Family Campground (Vineyard Haven) The family campground is a good option for an affordable and adventurous stay. All campsites are shaded and have private picnic tables. Open campfires are permitted (get out the smores)!

Harborview Hotel (Edgartown) Open since the summer of 1891, the Harborview Hotel is located just outside of Edgartown center at the end of an impressive row of historic whale captain’s homes. The hotel’s rooms, cottages, and suites share views of the Edgartown Lighthouse and Chappaquiddick Island. The property offers a variety of dining options, a heated outdoor pool, fitness center, children’s activities, and yoga classes.

Lambert’s Cove Inn (West Tisbury) Located on seven acres of West Tisbury land, this inn, farm, and restaurant offers a quiet country escape. Guests can visit the pool, spa, tennis courts, or private beach. The grounds are also home to fifty chickens and two goats!


Image above: photo by Wayne Smith

Mansion House (Vineyard Haven) is smack in the middle of Vineyard Haven’s quaint main street lined with shops, restaurants, and art galleries. Many rooms have views of the Vineyard Sound. Guests have access to a harbor viewing cupola, spa, and indoor pool.

Martha’s Vineyard Hostel (West Tisbury) Voted the world’s friendliest hostel three years in a row, this casual accommodation offers free breakfast and a sand volleyball court.

The Dockside Inn (Oak Bluffs) This harbor-side inn is family friendly, affordable, and stocked with complimentary ice cream treats. If you are seeking the buzzing party atmosphere of Oak Bluffs, this is the place to stay.



Beaches (All Island) Many beaches on the Vineyard are private — either belonging to a homeowner, or requiring a town sticker — but there are still plenty of amazing beaches open to the public if you look for them. Our favorites are Long Point Wildlife Refuge, State Beach, South Beach, Gay Head Town Beach (Moshup Beach), and Menemsha Public Beach.

Cape Poge Lighthouse Tour (Chappaquiddick, Edgartown) The Trustees of Reservation offers an excursion to the Cape Poge Lighthouse. Visitors can climb the 1801 lighthouse and explore the surrounding areas. On a clear day, you can see Nantucket from the top of the light. Guests travel in the bed of a pickup truck outfitted with benches, binoculars, and information. Our boys love this adventure!


Image above: photo by Kristen Leigh Conklin

Farm.Field.Sea (All Island) offers a variety of island experiences from cheese making and wine tasting to shellfish education and farm exploration, all alongside local farmers, fishermen, and chefs. Many Farm.Field.Sea adventures end with amazing meals in unique settings (think farm-to-table dinner inside a greenhouse).

Felix Neck Wildlife Sanctuary (Edgartown), a part of Mass Audubon, is a very special spot. The property has a nature center, butterfly garden, and pond exploration events for children. Adults can sign up for moonrise kayak quests (one of my favorite wedding gifts) and birding classes. Our kids love Felix Neck so much we hosted a 4th birthday party there.


Gay Head Cliffs (Gay Head) On the far western tip of the island sits the stunning clay cliffs of Gay Head. Along the cliffs sit a small number of shops and restaurants as well as a walking path to the beach.

Hikes through Cedar Tree Neck Sanctuary, Great Rock Bight Preserve, and the Menemsha Hills are some of our favorites on the island. All of these hikes are family-friendly with a mix of woodsy paths, beaches, and scenic overlooks.

Jumping from Jaws Bridge (Oak Bluffs, Edgartown) Jumping from State Beach’s bridge marking the line between Oak Bluffs and Edgartown is a right of passage. Infamous from the blockbuster Jaws, the landmark is as much a pop culture site as it is a swimming spot.


Martha’s Vineyard Camp Meeting Association (Oak Bluffs) In the 1860s and 1870s, hundreds of Methodist families began replacing their tent homes in Trinity Park with small wooden cottages. Today, the campground is made up of 300 colorful, ornate, family homes filled with rich history. The grounds are closed to heavy traffic, so a slow summer stroll is the perfect way to enjoy their beauty.

Musical Mondays at Featherstone Center for the Arts (Oak Bluffs) In the summer months, come watch local bands every Monday evening on a beautiful outdoor stage. Great for a picnic with a  bottle of wine and the kids.

Mytoi Gardens (Chappaquiddick, Edgartown) Nestled within Chappaquiddick is the intimate Japanese-style garden, Mytoi. Sheltered by a lovely pine grove, the preserve includes a small pond and island, non-native and native flowers and plants, footpaths leading past a birch walk and stone garden, and a trail winding toward Poucha Pond and the salt marsh.

Polly Hill Arboretum (West Tisbury) is a horticultural and botanical landmark of 20 cultivated acres plus 40 acres of protected woodlands. The grounds feature stone walls, meadows, and barns. If you are visiting with kids, make sure to pick up an explorer’s backpack at the visitors center full of child’s-size magnifying glasses, binoculars, and plant identification packets.

The Farm Institute (Katama, Edgartown) Ever wondered what it is like to be a farmer for a day? Kids as young as 2 can participate in the “Wee Farmers” program while older children and adults are invited to collect eggs, harvest crops, and tend to animals.

The Flying Horses Carousel (Oak Bluffs) is the nation’s oldest platform carousel. The wooden horses were built in 1876 and the carousel has been an Oak Bluffs attraction since 1884. Riders catch a ring with each round of the carousel — if you catch the brass ring you win a free ride!

The Martha’s Vineyard Film Festival (All Island) hosts summer film series, film festivals, and the beloved Cinema Circus (think artsy homespun circus followed by a parade into the theater for an amazing children’s movie — how magical is that!?).


The West Tisbury Farmer’s Market (West Tisbury) held on Saturday and Wednesday mornings is stocked with island-grown produce, meat, seafood, flowers, and treats. Among the booths are special snacks like egg rolls, freshly squeezed lemonade, raspberry ice, and popovers.

Tomahawk Fish Charters w. Captain Buddy Vanderhoop (All Island) Captain Buddy Vanderhoop has been fishing the Vineyard waters for more than 45 years. Capt. Vanderhoop comes from a long line of fishermen (his great uncle Amos Smalley harpooned “Moby Dick”). Keith Richards, Ted Danson, Spike Lee, and James Belushi have all fished from his boat.


Image above: photo by Yoga Barn

Yoga Barn (West Tisbury) What would a vacation (or long winter) be without a great yoga class, massage, or acupuncture session? The yoga barn’s idyllic rural setting is the perfect place to relax.

Do The Arts

Allen Whiting at The Davis House Gallery (West Tisbury) Allen Whiting was born on Martha’s Vineyard in 1946. He lives and works on his family’s sheep farm in West Tisbury, painting with oils in the open air.

Martha’s Vineyard Glassworks (West Tisbury) is a glassblowing studio and gallery full of gorgeous glassware and sculpture. Stop by to check out the team of artists in action.

Martha’s Vineyard Playhouse (Vineyard Haven) is a professional nonprofit theater in Vineyard Haven. The playhouse hosts year-round theater, children’s theater, and outdoor Shakespeare shows throughout the summer months.


The Field Gallery (West Tisbury), first started as an island co-op gallery in the 1970s and now represents 25 artists and showcases the enchanting sculptures of Field Gallery founder Thomas Maley.

The Granary Gallery, (West Tisbury) housed in The Red Barn Emporium, has a unique collection of antiques, sculptures, and paintings by island artists.

The Yard (Chilmark) is a contemporary dance, theater, and art space in Chilmark offering classes for children and adults. Performances from dancers and artists are held regularly throughout the season.

Vineyard Artisans Festivals (West Tisbury) Held every Thursday and Sunday during the summer season, the Vineyard Artisan Festivals are open-air markets full of locally made jewelry, furniture, rugs, quilts, and fine art.



Alley’s General Store (West Tisbury) is a classic Vineyard institution. Suppliers of “almost everything,” you can come here for a special hostess gift, vintage penny candy, or a new garden hose.

Bunch of Grapes Bookstore (Vineyard Haven) is a beautifully-curated bookshop filled with bestsellers for the beach, pretty cookbooks, and specialty gifts. The shop hosts author events, including those for Hillary Clinton and David McCullough. Presidents Clinton and Obama like to buy their summer reads here.

Chicken Alley Thrift Shop (Vineyard Haven) Purchases made at the thrift shop support Martha’s Vineyard Community Services, thus supporting islanders in need. Stop here for a used beach chair, book, or sun hat.


Citrine (Vineyard Haven) is a small boutique on Main Street in Vineyard Haven. The shop has women’s and children’s clothing as well as handmade bags and jewelry. My favorite items are the vaalbara bags and pieces by local jeweler Nettie Kent.

Pandora’s Box (Menemsha, Chilmark) this Menemsha boutique is the perfect spot for a new beach dress or special piece of locally made jewelry.

The Allen Farm (Chilmark) is Martha’s Vineyard’s oldest continuously working family farm, originally purchased in 1762. The farm consists of 100 acres of rolling pastures and meadows bounded by historic stonewalls, upper Chilmark Pond and the Atlantic Ocean beyond. The small farm shop offers one of a kind woolens (blankets, hats, sweaters, vests, and wool) as well as ibex, filson, and kinross products.

The Green Room (Vineyard Haven) is my favorite all-around clothing and shoe shop. I go here for new jeans, flip flops, and cute shoes for the boys. Downstairs, they have a full surf and skateboard shop with a great selection of boardshorts, sneakers, and gear.

Shop Farm Stands

Martha’s Vineyard is filled with farms growing produce, beef, pork, chicken, turkey, lamb, and eggs. Here is a list of my favorite roadside farm stands. Swing through one of these to grab just-picked goodies — your grill will thank you.

Beetlebung Farm (Chilmark) My picks – any produce.

Black Water Farm (West Tisbury) My picks – beef and pork sausage.


Fiddlehead Farm (West Tisbury) My pick – artisan cheese and dried pasta.

Ghost Island Farm (West Tisbury) My pick – all produce.

Green Island Farm (West Tisbury) My pick – eggs.


Mermaid Farm & Dairy (Chilmark) My pick – yogurt.

Morning Glory Farm (Edgartown) My pick – summer corn.

North Tabor Farm (Chilmark) My pick – salad greens.

Slip Away Farm (Chappaquiddick, Edgartown) My pick – all produce.

The Farm Institute (Katama, Edgartown) My pick – beef and pork.


The Grey Barn & Farm (Chilmark) My picks – raw milk and homemade cheese.


20 by Nine (Oak Bluffs) is a cozy restaurant just off Circut Ave in downtown Oak Bluffs. They focus on craft beer, whiskey, and small plates of locally-sourced food. Try a whiskey-based cocktail and charcuterie board after the beach.

Coop deVille’s (Oak Bluffs) motto is “any closer to the water and you’ll fall in,” which is true. If you’re looking for a festive atmosphere and great people-watching, pull up a stool here. The Coop offers an impressive beer selection along with wings, seafood, and a raw bar.

Sweet Life Cafe (Oak Bluffs) has an elegant outdoor bar tucked behind the restaurant. The atmosphere is relaxing and sophisticated with garden lights, large white umbrellas, and flowering plants. The bar has an extensive wine list as well as beer, wine, and specialty cocktails by the glass.

The Port Hunter (Edgartown) is a hip, popular bar in downtown Edgartown. Check their calendar for live music and come here to grab a drink and raw bar treat.

High-End Eating

20 by Nine (Oak Bluffs) More than a craft beer and whiskey bar (although those parts of the menu are impressive!) 20 by Nine offers small plates, large family-style dishes, charcuterie and cheese boards, and creative desserts. Grab one of the few tables outside and eat your way through the menu.

Chilmark Tavern (Chilmark) is an American bistro located up-island in Chilmark. The menu is based on island-grown produce, seafood, and meat. Just don’t forget to BYOB!

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Detente (Edgartown) is a modern seasonal kitchen with an emphasis on fresh and local ingredients. The frequent menu changes and nightly specials reflect what is growing on the island. Treat yourself to something really special and try the chef’s six-course tasting menu.

Lambert’s Cove Inn (West Tisbury) The inn and restaurant sits on the picturesque Lambert’s Cove Road. The dining room is charming and many dishes use produce and eggs grown on the property.

Red Cat Kitchen (Oak Bluffs) If you like (good) loud music and a young, hip atmosphere come eat at Red Cat Kitchen. The menu is dramatic, from local fish served whole to “Fu*kin’ Great Crispy Brussel Sprouts.”

State Road Restaurant (West Tisbury) Is an island favorite for brunch and dinner. The brunch menu offers items like local pork hash and lemon ricotta pancakes. The restaurant’s location and atmosphere is classic Vineyard — imagine a homey dining room in a perfectly decorated, shingled house complete with a front herb garden.

Sweet Life Cafe (Oak Bluffs) offers modern American cuisine in a romantic setting with seating inside a charming Victorian home or outdoors in a starlit garden. The staff prides themselves on “hosting presidents and beach bums with equal aplomb.”

The Beach Plum Inn (Menemsha, Chilmark) The hilltop location, overlooking Menemsha and the Vineyard Sound, is reason enough to dine here. Ask for a table outside and pack your own wine, then dig into beautifully prepared island food.

The Port Hunter (Edgartown) offers an exciting and spirited atmosphere. The menu changes often based on island ingredients. The kitchen offers a raw bar, creative vegetable dishes, above-average burgers, fish and chips, and tacos.

Casual Eating

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Image above: photos by Jocelyn Filey

7a Foods (West Tisbury) was our home away from home our first year on the island (as we lived across the street). 7a foods is a “farm-to-take-out” restaurant serving breakfast and lunch including baked goods, farm fresh salads, homemade soups, and artisan sandwiches. You should try everything, but start with an egg sandwich on a biscuit in the morning and either a Liz Lemon (hot housemade pastrami, turkey, swiss, coleslaw, Russian dressing and potato chips on rye) or Asparagus Melt (fontina, roasted garlic aioli, basil, dried blueberries and pickled red onion on focaccia) for lunch.

Rosewater (Edgartown) Roasewater market and takeaway just opened its doors last week. The new “it spot” is beautifully decorated and offers everything from sandwiches, prepared foods, coffee, baked goods, and fresh juices at its convenient downtown Edgartown location. I’m especially smitten with the serve-yourself sparkling water station – perfect for filling those beach canteens.


Art Cliff Diner & Food Truck (Vineyard Haven) Breakfast at the Art Cliff Diner is a must. The menu has everything from peach-stuffed french toast to cod cakes and spicy chicken hash. Go early as there is often a wait (but it’s worth it!). Late night, swing by the truck for garlic fries and a sandwich.

Backdoor Donuts (Oak Bluffs) A famous island experience, Backdoor Donuts lives up to the hype. From 7 pm to 12:58 am line up behind Martha’s Vineyard Gourmet Bakery & Cafe for just-fried donuts and super-sized apple fritters.

Behind the Bookstore (Edgartown) Tucked off the main drag, this small coffee shop has a beautiful patio, unique espresso drinks, baked goods, and light lunch options. The barista created the BTBama iced latte for President Obama with four shots of espresso and topped with grapefruit zest.

Ben & Bill’s Chocolate Emporium (Oak Bluffs) This is our favorite summer ice cream spot. You can’t go wrong with the classic flavors, but if you’re feeling adventurous you can try their lobster ice cream (made with real lobster).

Blissed Out (Vineyard Haven) blends up organic smoothies, cold-pressed juices, frozen acai “superfood ice cream” and more. When it’s really hot and I’m too grumpy to cook I come here for a Paradise smoothie.

Grace Church Lobster Rolls (Vineyard Haven) Voted “Best of the Vineyard,” the lobster rolls served out of Grace Church on Friday evenings are an island treasure. Lines form around 4 pm for the 4:30 to 7:30 dining time. The lobster rolls are simply made with fresh lobster meat, a touch of mayo, and white pepper. Hot dogs, pie, and drinks are also available.

Little House Cafe (Vineyard Haven) is open year-round serving breakfast, lunch, and dinner. Our favorites are the fish tacos and the strawberry shortcake.


Menemsha (Menemsha, Chilmark) is a small fishing village in Chilmark. The dead-end road to the beach is lined with fish markets. For dinner, either order a simple seafood plate from a market (boiled lobster, stuffed quahogs, etc.) or bring your own picnic. Set up a blanket on the beach, pop a bottle of wine, and watch the sun set over the ocean.

Morning Glory Farm (Edgartown) More than a farm stand, Morning Glory Farm bakes up delicious homemade breakfast treats from muffins to zucchini bread. The farm also has an impressive salad bar, soup station, and prepared foods to go. This is a great place to grab provisions for the beach and dinner fixings.

Orange Peel Bakery (Gay Head) Located in remote Gay Head, the Orange Peel Bakery is a fully operating bakery making breads, granola, cookies, and treats. Pizza night is every Wednesday (May-October) and Saturday (May & November) from 5 to 8. Bring your own topping to contribute to the family-style assembly and watch the pies cook in the beautiful outdoor stone oven. Suggested donation of $10 per person.

The Scottish Bakehouse (Vineyard Haven) Open year-round, the bakehouse is a one-stop shop for homemade breads, pies, and cookies. The busy cafe turns out breakfast, lunch, and early dinner options. There are a handful of picnic tables and bench seating outside. We love the egg sandwiches, plate dinners, amaretti fingers, and brownies.

Special Summer Events: These annual events are some of our favorite days of the year. Plan accordingly to check out the The Martha’s Vineyard Agricultural Society’s Fair (in West Tisbury at the end of August), a classic country fair with livestock shows, baking contests, rides, and delicious concessions.


Grand Illumination Night (in Oak Bluffs mid-August) is when the campground “gingerbread cottages” are decorated in paper lanterns — an amazing sight.

Firework displays are held in Edgartown on July 4th and in Oak Bluffs in mid-August.

The Possible Dreams Auction (in Edgartown in late July) raises money for Martha’s Vineyard Community Services. Past auctioned “dreams” have been a private Carly Simon concert, walk across the Brooklyn Bridge with David McCullough, and a Ghostbusters set tour with Dan Aykryod.


I hope you come to visit us and when you do, rather than buying another t-shirt as a souvenir, pick up a bar of Not Your Sugar Mamas’ locally produced superfood chocolate, a round of Flat Point Farm’s goat milk soap, a bag of Chilmark Coffee, a pouch of Martha’s Vineyard Sea Salt, and one of Susie Middleton’s cookbooks to remember your stay.

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    • Hi,

      Thank you posting this place. I always want to visit there. Thank you for posting these beautiful pictures with comments on each picture. Is there any history of musuem? I understand there was once where deaf community was in there and everybody including hearing people were signing language.

      Thanks again for posting this place.

      :-) joy

  • The NYTs just ran “36 Hours on Martha’s Vineyard.” Yours is much better (based on one glorious, free summer on the island post college).

  • Is this trip something you save up for? Or if its something someone can do on a budget? Either way I would love to visit this area some day.

  • Thank you Katie! One glorious summer is enough to hook you for life!

    Carina – you can definitely visit the island on a budget if you plan accordingly. I would look into spring and fall specials and check out a few of the camping/hostel options I included. I hope you can swing it!

  • If you’re looking for amazing on-budget eats (or just love an incredible burrito) you should definitely check out La Choza in Vineyard Haven. It’s an easy walk from the boat, right on the corner of Main & State Rd. The burritos are super big, so be prepared! As a plus, it’s owned & run by a native, so you’re supporting real local business. Enjoy!

  • I’ve spent every summer on the Vineyard since I was in the womb, from the day school got out (literally) to Labor Day, and lived there full time for a year.

    This list is on point. Great recommendations, and way better than any of the lists the NYT has created.

  • Such a great, comprehensive guide with something for everyone and every budget and so many spots and things to do that most tourists would never know of. Completely agree with Katie! Much better than the NYTimes 36 Hours!

  • I loved this piece! I’ve been to Martha’s Vineyard twice and have done a lot of the things on this list but not everything — next time I go, I have the perfect list of to do’s!

  • I’ve always wanted to visit the Vineyard! Love your tour of favorite places. Thanks for sharing this. Love the pics and descriptions!

  • Thank you, very informative ! This will be very helpful. Very excited to be spending a weekend in Martha’s Vineyard very soon as we are touring Maine, Vermont and some of Cape Cod.

  • So glad I looked on pinterest. My daughter has planned a Mom daughter trip. We will be there August 30th thur Sept. 2. Thank you so much for your local flare and blessings to make our trip about
    learning and respecting your home place