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Lifestyle
Gray's Guides
Martha's Vineyard

Martha's Vineyard

Tucked just south of Cape Cod, Martha’s Vineyard is a quintessential New England escape—known for its windswept beaches, charming villages, and timeless summer nostalgia. Sailing past Edgartown harbor or watching the sunset over Menemsha, every corner of the island feels like a postcard come to life.

Stay

From family-run inns to world-renowned luxury resorts, find a welcoming home away from home.

Harbor View Hotel

Iconic Edgartown property with luxe updates, unbeatable views, and classic island elegance.

Lambert's Cove Inn

A romantic, tucked-away hideout with serene coastal vibes and a dreamy on-site restaurant.

Edgartown Collection

A chic group of boutique stays in the heart of Edgartown—modern meets historic charm.

Winnetu Oceanside Resort

Perfect for families, with beach access, lawn games, and an easygoing summer energy.

Summercamp

A playful, retro-inspired hotel overlooking the harbor, blending nostalgia with modern comforts.

Faraway

A stylish boutique property in the heart of Edgartown, offering chic coastal décor and a laid-back, luxurious vibe.

Beach Plum Inn

A romantic escape with sweeping views of Vineyard Sound that describes itself as “Summercamp for grown-ups.”

Oak Bluffs Inn

A charming Victorian inn just steps from the beach and the vibrant shops and restaurants of Oak Bluffs.

Eat

Dining out is an essential part of any travel experience. Explore our favorite restaurants, bars, and more.

The Black Dog Tavern

An iconic Vineyard Haven staple serving hearty New England classics with harbor views and a side of local history.

7a Foods

A cozy West Tisbury staple known for its breakfast sandwiches, freshly baked pastries, and picnic-perfect lunches.

Beach Road

Elevated coastal fare in Vineyard Haven—don’t skip the gourmet hot dog, it’s a local favorite.

State Road

The sister spot to Beach Road, this intimate restaurant is ideal for a slow, delicious meal in the up-island countryside.

Outermost Inn

Perched above the cliffs in Aquinnah, it’s a stunning destination for a romantic dinner or special occasion.

Chilmark Tavern

Upscale but relaxed, with a hyper-seasonal menu and a cozy, community-driven vibe.

L’étoile

A fine-dining experience set inside a stately captain’s home, with an elegant menu to match.

The Terrace

Elegant fine dining with classic Vineyard charm.

Larsen’s Fish Market

A Menemsha favorite for ultra-fresh seafood—don’t miss their famous lobster roll enjoyed dockside.

Iggy’s Bread

Beloved for its freshly baked breads, pastries, and treats, perfect for breakfast on the go or a picnic spread.

Drink

Dining out is an essential part of any travel experience. Explore our favorite restaurants, bars, and more.

Harbor View Hotel

Sip craft cocktails or chilled rosé on the veranda with sweeping views of Edgartown Lighthouse and the harbor.

Nancy’s

A lively Oak Bluffs institution where the Donovan's Dirty Banana cocktail is practically mandatory.

Nomans

Great spot for casual drinks with live music most nights.

Alchemy

Alchemy is a stylish spot in Edgartown serving fresh coastal dishes and creative cocktails in a warm, inviting atmosphere.

What to do

Immerse yourself in local activities — including world-class golf courses, beaches, spas, parks, and more.

Jaws Bridge

A rite of passage for locals and visitors alike—equal parts thrilling and nostalgic.

Morning Glory Farm

A beloved family-run farm stand offering fresh produce, baked goods, and flowers, perfect for a morning visit or picnic supplies.

Catboat Charters

Set sail on a beautifully restored wooden catboat and take in Edgartown’s harbor from the water.

Island Alpaca Farm

Stop by to feed and pet these friendly alpacas just a short drive from Vineyard Haven.

West Tisbury Farmers Market

Live music, fresh flowers, and some of the best bites on the island, all under the trees. Stop by Fire Cat Farm for beautiful, fresh flowers!

Edgartown Village Market

A Tuesday favorite filled with artisan crafts, handmade goods, and farm-grown produce.

Nomans

A family-friendly spot with lawn games, live music most nights, and plenty of room for pups to sprawl.

Vineyard Sound

Catch this all-male a cappella group performing at local spots—fun, musical, and very MV.

Nell and Nell Home

A beautifully curated home store offering coastal-inspired décor, textiles, and unique accents.

Island Outfitters (Oak Bluffs)

A go-to for casual Vineyard style, from beachwear to everyday essentials.

Sea Legs (Edgartown)

A chic boutique with stylish resort wear, accessories, and vacation-ready looks.

Green Room

A laid-back surf and lifestyle shop carrying apparel, gear, and Vineyard-branded favorites.

Back Door Donuts

A legendary Oak Bluffs bakery serving warm, oversized donuts and fritters from its late-night back door.

Tote-Ally Yours

A charming shop for Vineyard-inspired tote bags, accessories, and gifts.

The Arcade

A nostalgic, family-friendly spot for classic games, skee-ball, and rainy-day fun.

Culture

Discover local art museums, theaters, landmarks, festivals, and more.

Aquinnah Cliffs

Stunning multi-colored clay cliffs overlooking the ocean, with a beach below for exploring.

The Tabernacle in Oak Bluffs

An iconic open-air venue for concerts, community gatherings, and the beloved Grand Illumination Night.

The Vineyard Playhouse

The island’s professional theater presenting plays, readings, and live performances in the heart of Vineyard Haven.

Old Whaling Church

A striking 19th-century Greek Revival building now hosting concerts, lectures, and community events.

The Campgrounds

A charming cluster of colorful, Victorian-era homes in Oak Bluffs that feel straight out of a storybook.

Flying Horses Carousel

Ride the oldest platform carousel in the country and try your luck at grabbing the brass ring.

Gallery Hopping

Martha’s Vineyard is known for its vibrant arts scene and exceptional local and national talent, with must-visit stops including Untamable Gallery, Granary Gallery, and North Water Street Gallery.

Martha’s Vineyard Museum

The island’s flagship museum chronicling Vineyard history, art, and culture through engaging exhibits and programs.

MVAAFF

Martha’s Vineyard African American Film Festival- Held every August, this acclaimed festival showcases powerful storytelling from Black filmmakers and industry leaders.