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December 17, 2022
Chilmark, MA

Alexandra & JJ

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    Our Guide to the Island

Our Guide to the Island

With 96 square miles of harbor towns, lighthouses, beaches, and farmland, there's no shortage of things to do on Martha's Vineyard. Over the years, we've made special memories at and become quite attached to many places on Martha's Vineyard. Here's a (pretty exhaustive) guide to some of our favorite spots - we hope you love them as much as we do.
For Celebrity Sightings, Hippie Vibes, and Local Flavors - West Tisbury Farmer's Market

For Celebrity Sightings, Hippie Vibes, and Local Flavors - West Tisbury Farmer's Market

35 Panhandle Rpad, West Tisbury, MA

Deborah Previdi's #1 Recommendation on Martha's Vineyard! Held rain or shine since 1974, every Saturday morning in the summer you will find the Previdi family at the West Tisbury Farmer's Market. The market runs from 9am-12pm every Wednesday and Saturday from mid-June through October and features local farms, artisans, and live music. Can't miss: cheese from Grey Barn, corn from Morning Glory Farm, make-your-own-bouquets from Tea Lane Farm, honey from Island Bee Company, oysters from Spearpoint Oysters, pie bites/pie/quiche from Pie Chicks, egg rolls from Khen's Kitchen, fried chicken sandwiches from Komrade Fried Chicken (JJ's top pick), all the chocolates from Salt Rock Chocolate, popsicles from Yommi Pops, West Tisbury Traffic Jam from New Lane Sundries, Citrus Coolers from Good Tastes, and coffee from Chilmark Coffee, smoked yellowfin dip from MV Smokehouse (Richard’s favorite).

If You Love Cheese and Baby Farm Animals - The Grey Barn and Farm

If You Love Cheese and Baby Farm Animals - The Grey Barn and Farm

22 South Road, Chilmark, MA 02535
, (508) 645-4854

A Previdi family favorite since they opened in 2009, the Grey Barn and Farm is an almost-daily destination for us each summer. Sign up for a group or private farm tour, which includes a tasting of Grey Barn's award-winning cheeses and/or vegetables. Or visit the charming farmstand to buy their cheese, home-baked bread and pastries, fresh-from-the-field produce, and an array of home goods and books. Our favorite ways to enjoy Grey Barn's cheeses: Eidolon with honey and green apple; Prufrock with apricot jam or cured meat and cornichons; Bluebird with fig jam, dark chocolate or dessert wine. Can't miss: all of the cheese, all of the homemade breads and pastries (croissants, Kouign Amann, milkbread...need we say more?), fresh eggs, fresh milk, heirloom tomatoes, cutting boards crafted from MV trees by a local teen, and a well-curated selection of books.

For a Floating Raw Bar Experience - Cottage City Oyster Farm

For a Floating Raw Bar Experience - Cottage City Oyster Farm

Oak Bluffs, MA
, (508) 299-7745

Get a literal taste of New England. Tour the oyster farm and enjoy a 1-hour "floating raw bar" experience aboard a 31' open-deck boat.

If You Want to Golf like Barry O - Farm Neck Golf Club

If You Want to Golf like Barry O - Farm Neck Golf Club

1 Farm Neck Way, Oak Bluffs, MA 02557
, (508) 693-3057

Book a tee time and enjoy golf with an ocean view. We can’t promise you’ll see the Obamas - but we can’t promise you won’t.

If You Want To Do Some Water Sports - Island Spirit Kayak

If You Want To Do Some Water Sports - Island Spirit Kayak

Edgartown Oak Bluffs Road, Oak Bluffs, MA 02557
, (508) 693-9727

Island Spirit will deliver kayaks and stand-up paddle boards to you anywhere on the island if you call a day or two in advance, including any of the island's public and private beaches. They also do a number of different kayak/SUP tours for adults, families, and kids - Deborah and Richard recommend the Sunrise Kayak Tour with Island Spirit's owner Chick, which includes breakfast and coffee as you float. From experience, no one will be upset if you bring your own bubbly to make mimosas :)

For Some Peace and Quiet Off the Beaten Path - Drive on the Beach with an Over-Sand Vehicle Permit

For Some Peace and Quiet Off the Beaten Path - Drive on the Beach with an Over-Sand Vehicle Permit

Martha's Vineyard,

If you'll have a 4WD/AWD vehicle on the island, you can explore thousands of acres of open beach with an Over-Sand Vehicle Permit, available from The Trustees website. Find the perfect spot for fishing, nature viewing, beach exploration, swimming, or a family adventure. We recommend checking out Norton's Point in Katama. Note: Over-Sand Vehicle permits need to be purchased online in advance. Permits start at $70.

If You Want to Take in Some Views/History While Raising Your Heart Rate - Hike the Brickyard

If You Want to Take in Some Views/History While Raising Your Heart Rate - Hike the Brickyard

Chilmark, MA

Visit the remains of New England's first commercial brickyard that built much of downtown Boston. Most of the brickyard has been reclaimed by nature, but you can enjoy beautiful ocean and nature views peppered by old machinery along this 3-mile roundtrip hike. Note: the uphill hike on the way back is mildly strenuous.

For a Private Adventure on the High Seas - Island Girl Excursions

For a Private Adventure on the High Seas - Island Girl Excursions

7 Great Plains Road, West Tisbury, MA 02575
, (774) 563-8323

Eamonn and Rebecca of Island Girl Excursions will pick you up via boat in Vineyard Haven, Oak Bluffs, Edgartown, or West Tisbury, and take you for a private journey around the island or nearby sites like Naushon Island (privately owned by the Forbes family), Cuttyhunk, Tarpaulin Cove, Kettle Cove, and Nashawena Island (famous for its Scottish Highland cattle who like to hang out in the ocean).

For the Very Best Wine, Beer, and Spirits - Vintage MV Wine & Spirits

For the Very Best Wine, Beer, and Spirits - Vintage MV Wine & Spirits

29 Winter Street, Edgartown, MA 02539
, (774) 549-9287

An amazing selection of beer, wine, and liquor in downtown Edgartown. Owner John Clift is incredibly knowledgeable about wine and beer, and curates the store's assortment himself - tell him JJ sent you ;) Can't miss: Washashore Ale (John's own beer label), an excellent selection of rosé wines, and hard-to-find wines and spirits from all over the world

If You Want Food, Drinks, Music, and Lawn Games - Nomans

If You Want Food, Drinks, Music, and Lawn Games - Nomans

15 Island Inn Road, Oak Bluffs, MA 02557
, (508) 338-2474

The outdoor dining area at Nomans is like a big backyard where everybody is welcome. Guests come for the food but stay for the lawn games and picnic tables – it’s a great place to meet your friends or bring the entire family, and often has live music. Nomans also makes their own very delicious rum. Dogs are welcome! Can't miss: poke bowl, painkiller. **No reservations.**

For the Very Best Burgers and a Speakeasy Vibe - Brick Cellar Bar

For the Very Best Burgers and a Speakeasy Vibe - Brick Cellar Bar

137 Main Street, Edgartown, MA 02539
, (508) 627-5850

A swanky bar/restaurant in the brick-walled basement of Atria serving the best burgers you'll ever have. It will be closed for dinner the Friday of our wedding, but Brick Cellar is perfect for dinner on Thursday or Sunday. Can't miss: All of the burgers are spectacular (JJ’s go-to is the Fast Eddie, Alexandra favors the Atria Classic), so definitely get a burger and opt for the truffle fries, then order a side of the off-menu lobster mac and cheese. **Reservations Required.**

If You Want a Jaw-Dropping Sunset and Romantic Dinner - The Outermost Inn

If You Want a Jaw-Dropping Sunset and Romantic Dinner - The Outermost Inn

81 Lighthouse Road, Aquinnah, MA 02535
, (508) 645-3511

The best fine dining and most famous sunsets on the island, make a reservation to dine at this romantic inn owned by the Taylor family. With a gorgeous view right at the foot of the Aquinnah lighthouse, you'll want to arrive early for your reservation and enjoy a glass of champagne at the backyard bar as the sun sets. Heck, might as well get some oysters too and really enjoy yourself. **Reservations Required.**

For Sit-Down Oysters and Lobster Rolls - 19 Raw Oyster Bar

For Sit-Down Oysters and Lobster Rolls - 19 Raw Oyster Bar

19 Church Street, Edgartown, MA 02539
, (774) 224-0550

A quaint restaurant in downtown Edgartown that's owned by John Clift of Vintage MV (so you know the drink selection is on point) and is perfect for lunch or dinner. Can't miss: all of the oysters, any of the crudos, the lobster roll is our favorite on the island (but only available at lunch). **No Reservations** but plan for a bit of a wait once you put your name on the waitlist, it's very popular.

If You Want Lobstah and Chowdah - The Net Result

79 Beach Road, Tisbury, MA 02568
, (508) 693-6071

A fish market and a takeout operation in one. We love to grab a picnic table out front for takeout on a laidback night, or hit the Net Result right when we get off the ferry and are starving for some chowder. The Net Result is BYO, so grab a bottle of wine and a picnic table out front, and enjoy some local seafood. Can't miss: New England clam chowder, whole steamed lobster, peel & eat shrimp, fried clams, steamers, swordfish sandwich, sushi, key lime pie by the slice. Their fries are also really, really good. **No Reservations** Order at the counter.

For a (BYO) Drink in a Dry Town - Chilmark Tavern

For a (BYO) Drink in a Dry Town - Chilmark Tavern

9 State Road, Chilmark, MA 02535
, (508) 645-9400

A tavern in a dry town? Only in Chilmark. BYO wine, beer, or liquor (or all three, we’re here to celebrate!) to Chilmark Tavern and they’ve got the mixers to whip up just about any cocktail you can think of. We love their Basil Lime Martini if you want to bring vodka or gin, or their Painkiller is fantastic if you've got rum. Can't miss: Point Judith squid salad (a must for calamari lovers), mussels (great as an appetizer, even better with a side of fries as an entree), ice cream sundae. The pistachio pretzel crunch on the sundae is out of this world. **Reservations Required**

For "Farm-to-Takeout" Lunch-on-the-Go - 7A Foods

For "Farm-to-Takeout" Lunch-on-the-Go - 7A Foods

1025 State Road, West Tisbury, MA 02575
, (508) 693-4636

An upisland hotspot for sandwiches and baked goods using ingredients from local farms, 7A is most famous for the Liz Lemon sandwich (house-made pastrami, turkey, Swiss cheese, Russian dressing, and potato chips on rye bread), but it's hard to go wrong with any of their sandwiches. We stop by 7A multiple times a week during the summer for breakfast sandwiches on the way to golf and lunch to take to the beach. Insider's tip: If you call ahead to place your order, you can skip the wait. Can't miss: breakfast sandwich (add everything), chicken salad sandwich, Asian pulled pork sandwich, Liz Lemon sandwich, Umami Tsunami (gotta order right when they open, they go fast), homemade brownies.

If You're In the Mood for Donuts, Day or Night - Back Door Donuts

If You're In the Mood for Donuts, Day or Night - Back Door Donuts

1-11 Kennebec Avenue, Oak Bluffs, MA 02557
, (508) 693-3688

A Vineyard tradition. Doughnuts after dark might sound a little scary, but chocolate coconut doughnuts and apple fritters from the back (or front) door are something you’ll only want to run toward. Can't miss: Apple fritters, Chocolate-frosted party sprinkles donut, Maple bacon donut.

For a Jersey-Approved Diner - ArtCliff Diner

For a Jersey-Approved Diner - ArtCliff Diner

39 Beach Road, Tisbury, MA 02568
, (508) 693-1224

Since 1943, ArtCliff Diner has been serving creative diner food made from scratch. And we're from New Jersey, so you can trust our recommendations when it comes to diner food. Can't miss: Huevos rancheros, banana pancakes, and really anything on the menu. They're all classics.

For Some Fancy Cocktails Downtown - Alchemy Bistro & Bar

For Some Fancy Cocktails Downtown - Alchemy Bistro & Bar

71 Main Street, Edgartown, MA 02539
, (508) 627-9999

For stiff cocktails in an upscale environment, skip the downstairs and grab a seat at the second-floor bar at Alchemy.

For Lunch or Drinks with a Water View - The Atlantic Restaurant

For Lunch or Drinks with a Water View - The Atlantic Restaurant

2 Main Street, Edgartown, MA 02539
, (508) 627-7001
If You’re Looking for the Late Night Scene in Edgartown - The Port Hunter

If You’re Looking for the Late Night Scene in Edgartown - The Port Hunter

55 Main Street, Edgartown, MA 02539
, (508) 627-7747
For local produce - Morning Glory Farm

For local produce - Morning Glory Farm

Edgartown, MA 02539
, (508) 627-9003

The biggest and busiest local farm stand - you can do pretty much all of your grocery shopping at Morning Glory. They’re especially famous on the island for their corn. Can’t miss: 7-Layer Magic Bar, Brownies, any produce but especially corn, homemade quiche, blueberry muffins, goldbud peaches.

For Picnic Supplies - Black Sheep

For Picnic Supplies - Black Sheep

17 Airport Road, Edgartown, MA 02539
, (508) 338-7770
For fine dining away from the hustle and bustle, but not too far away - State Road Restaurant

For fine dining away from the hustle and bustle, but not too far away - State Road Restaurant

688 State Road, West Tisbury, MA 02575
, (508) 693-8582

One of the few island restaurants open year-round, State Road is reminiscent of an old tavern, with a great stone fireplace, rough-hewn beams, artwork from local artists, and whimsical antiques. The contemporary American cuisine is sourced from regional farmers and fishermen, with many herbs, fruits, and vegetables harvested from its own gardens. The coffee bar and pastries are a big draw on weekend mornings as well - and if you’re closer to Vineyard Haven, check out their sister restaurant Beach Road. Can’t miss: homemade ricotta, mussels, duck, burger. **Reservations Required.**

For “Sea-to-Table” dining and a lagoon view - Beach Road Restaurant

For “Sea-to-Table” dining and a lagoon view - Beach Road Restaurant

79 Beach Road, Tisbury, MA 02568
, (508) 693-8582

With its ample windows looking out to the serene lagoon, lofted ceilings, and mellow globe lighting held aloft by sturdy ropes, the decor aptly reflects the kitchen's "sea-to-table" theme for its seasonally inspired and locally sourced offerings. The massive bar is a popular spot for dining and cocktails, especially during the $1 oyster happy hour. Can’t miss: oysters, blue crab lettuce cups, fried chicken, hot dog. **Reservations required.**

For the Best Ice Cream - Mad Martha's Edgartown

For the Best Ice Cream - Mad Martha's Edgartown

7 North Water Street, Edgartown, MA 02539
, (508) 627-8761

Don't be fooled by any other ice cream places on the island - Mad Martha's is THE place. Locations in downtown Edgartown, Oak Bluffs, and Vineyard Haven. Be warned: they're a cash only operation. Can't miss: Lotsa Dough (ice cream and froyo), MV Sea Salt Caramel, Sinful Chocolate, Black Raspberry

To Get Your “Jaws” Fix and a Lobster Roll - Menemsha Galley

To Get Your “Jaws” Fix and a Lobster Roll - Menemsha Galley

515 North Road, Chilmark, MA 02535
, (508) 645-9819

Menemsha is a charming fishing community within Chilmark that is the inspiration for Amityville in “Jaws” and the Menemsha Galley is one of the go-to spots in the neighborhood. Line up at this charming family-owned spot, around for more than 70 years, for everything from chowder to fresh swordfish sandwiches to soft serve ice cream. Once you pick up your order, enjoy it sitting on the rocks at the harbor or head to the beach around the corner. Parking can be tough at night, but it’s worth it to enjoy a dipped cone while watching the sunset over the harbor. It’s also a great place to pick up lunch if you’re up island in the middle of the day. Can’t miss: swordfish sandwich, lobster roll, fried clams, French fries, clam chowder, dipped cone. **No Reservations** you order from the counter and can take your food to go or eat at the picnic tables around back overlooking the harbor

To Rent Some Wheels - Edgartown Bicycles Rental

To Rent Some Wheels - Edgartown Bicycles Rental

212 Upper Main Street, Edgartown, MA 02539
, (508) 627-9008
If You're Up for Leisurely Wandering - Explore Downtown Edgartown

If You're Up for Leisurely Wandering - Explore Downtown Edgartown

Edgartown, MA

There's no shortage of quaint shops, galleries, and restaurants in Edgartown. Some of our favorite shops: Nell, Slate, Salte, CB Stark Jewelers, Backwater Trading, Portobello Road, North Water Gallery, and the flagship Vineyard Vines store. If you're looking for the iconic Over-Sand Vehicle Permit shirts, those can only be purchased at Wish U Were Here on Dock Street. We recommend wrapping up with a walk along North Water Street - lined with charming, historic whaling captains' homes from the 1600s and 1700s - to the Harbor View Hotel (about an eight minute walk), where you can grab a drink at Bettini.

TigerHawk Sandwich Co.

TigerHawk Sandwich Co.

12 Circuit Avenue, Oak Bluffs, MA 02557
, (508) 338-7306

Can’t miss: Beach Please breakfast sandwich, K-Pop in the Morning breakfast sandwich, Bahn Mi, Pole Bowls.

For "Fun for All Ages" - Flying Horses Carousel

For "Fun for All Ages" - Flying Horses Carousel

15 Oak Bluffs Avenue, Oak Bluffs, MA 02557
, (508) 693-9481

A National Historic Landmark, this is the nation's oldest continuously operating merry-go-round. Handcrafted in 1876—the horses have real horsehair and glass eyes—and brought from Coney Island in 1884, the ride gives children a taste of entertainment from an era before smartphones.

For Casual Eating and Drinking with a Stunning View - The Seafood Shanty

For Casual Eating and Drinking with a Stunning View - The Seafood Shanty

31 Dock Street, Edgartown, MA 02539
, (508) 627-8622
For a romantic dinner in Edgartown - Detente

For a romantic dinner in Edgartown - Detente

15 Winter Street, Edgartown, MA 02539
, (508) 627-8810

A dark, intimate wine bar and restaurant with hardwood floors and richly colored banquette seating, Détente serves more than a dozen wines by the glass as well as numerous half bottles. Even if you're not much of an oenophile, it's worth a trip just for the innovative food, much of it from local farms and seafood purveyors. Detente also offers outdoor dining in their courtyard. Can’t miss: Heirloom tomato panzanella, grilled octopus, any pasta.

For a beach that’s walking distance - Fuller Street Beach & Edgartown Lighthouse

For a beach that’s walking distance - Fuller Street Beach & Edgartown Lighthouse

Edgartown, MA 02539

Originally built in 1828, the current Edgartown Lighthouse stands on shore, accessible by a walking path in front of the Harbor View Hotel on North Water Street.

If you’re looking for something to eat in Aquinnah - Orange Peel Bakery

If you’re looking for something to eat in Aquinnah - Orange Peel Bakery

22 State Road, Aquinnah, MA 02535
, (508) 645-2025

A micro bakery producing breads, pastries, and pizza from scratch.

For the freshest fish on the island - Larsen's Fish Market

For the freshest fish on the island - Larsen's Fish Market

56 Basin Road, Chilmark, MA 02535
, (508) 645-2680

Newly renovated for Summer 2022, Larsen’s Fish Market is both a fish market and a restaurant, with the option to have fresh seafood prepared for you or take something home to cook yourself. The Larsen Family has been fishing in Martha’s Vineyard for generations and they are our go-to for fresh fish. We also love to order oysters from the “raw bar” - shucked and served on paper plates - to eat outside on the dock. Can’t miss: raw oysters and clams, lobsters, fresh fish.

Chilmark General Store

Chilmark General Store

7 State Road, Chilmark, MA 02535
, (508) 645-3739

Can’t miss: Road Race sandwich, meatball sub, turkey cranberry sandwich, Tuscan kale salad, Asian chicken salad, Island Grown pizza, Stonewall pizza.

Alley's General Store

Alley's General Store

1045 State Road, West Tisbury, MA 02575
, (508) 693-0088
Pie Chicks

Pie Chicks

395 State Road, Tisbury, MA 02568
, (508) 693-0228

Can’t miss: homemade quiche, strawberry rhubarb pie, peach blackberry lattice pie, triple berry crumble, chocolate cream pie, key lime pie, pie bites, chocolate chip cookies.

Island Alpaca Company

Island Alpaca Company

1 Head of the Pond Road, Oak Bluffs, MA 02568
, (508) 693-5554
Mermaid Farm & Dairy

Mermaid Farm & Dairy

9 Middle Road, Chilmark, MA 02535
, (508) 939-0140
North Tisbury Farmstand

North Tisbury Farmstand

632 State Road, West Tisbury, MA 02575
, (508) 696-4664
For Hiking Aficionados - Download the TrailsMV App

For Hiking Aficionados - Download the TrailsMV App

TrailsMV is a free app available for iPhone and Android, and provides you with up-to-date information on the more the 200 miles of public trails across Martha’s Vineyard. Google Maps can be a bit off when it comes to island trails, so TrailsMV can help you not only discover a variety of places to explore, but help you safely navigate them as well.

Aquinnah Cliffs Overlook

31 Aquinnah Circle, Aquinnah, MA 02535

A National Historic Landmark, the spectacular Aquinnah Cliffs are part of the Wampanoag Reservation land. These dramatically striated walls of red clay are the island's major attraction, as evinced by the tour bus–filled parking lot. Native American crafts and food shops line the short approach to the overlook, from which you can see the Elizabeth Islands to the northeast across Vineyard Sound and Nomans Land Island, a wildlife preserve, 3 miles off the Vineyard's southern coast.

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