Your Oak Bluffs

Escape Awaits

From sandy beaches to historic landmarks, Oak Bluffs offers endless ways to enjoy Martha’s Vineyard.

This guide highlights the best experiences to make your stay unforgettable.

Landmarks & Outdoor Fun

Flavors of Oak Bluffs

Martha’s Vineyard Events

Island Treasures

Beaches

Sun, Sand, and Serenity

Where you can experience the rare beauty of a freshwater lake on one side and the ocean on the other. Rent a canoe and enjoy the stillness of the lake, surrounded by nature.

Long Point Beach

(Moshup Beach) near the Gay Head Cliffs and lighthouse, take in the spectacular red clay cliffs and panoramic ocean views that are truly unforgettable.

Aquinnah Public Beach

If you’re in the mood to unwind away from the crowds, head to Tashmoo Beach. Tucked off the beaten path, it’s peaceful, quiet, and the perfect spot to relax and recharge.

Tashmoo Beach

(Katama Beach) in Edgartown provides lively, scenic views and incredible waves lapping up on beautiful sand.

South Beach

It’s worth the long drive to a quiet, charming fishing village for spectacular sunset views with families cooking out or eating local seafood on the beach.

Menemsha Beach in Chilmark

(Between Oak Bluffs & Edgartown) is a family-friendly beach with calm, warm, and shallow water perfect for kids. Best for swimming, kayaking, and paddle boarding or a jump off the famous Jaws Bridge.

Joseph Sylvia State Beach

Saving my favorite for last, the famous Oak Bluffs hangout is perfectly located steps from all the delicious food Circuit Avenue has to offer with the gorgeous Ocean Park as its backdrop. Come as early as 8am for yoga with Christopher or for water workouts with the legendary Polar Bears during the summer, or come in the afternoon for picnics and parties.

Inkwell Beach

Explore Beyond the Shore

Flying Horses Carousel

The oldest operating platform carousel in the U.S., built in 1876. A nostalgic ride for all ages.

These colorful Victorian-style homes in the Martha’s Vineyard Camp Meeting Association are a photographer’s dream

Gingerbread Cottages

Martha’s Vineyard Museum

Dive into the island’s rich maritime and Native American history

Pirate Adventures Martha’s Vineyard

A fun, interactive treasure hunt on a pirate ship—especially great for families with kids

Martha’s Vineyard Sightseeing Tours

A 2.5-hour island tour that includes a stop at the iconic Gay Head Cliffs and lighthouse

High Tide Fishing Charters

Offers light tackle and fly fishing for striped bass, bluefish, and more.

Held Sundays at Washington Park, this market features local artisans, food, flowers, and live music

Oak Bluffs Open Market

Martha’s Vineyard

Events All Year Round

  • August 7, 2026 - First Friday Vineyard Haven

Boutiques & Vineyard Finds

Favorite keepsakes, etched stones, cards, and signs

Best and most popular souvenirs (I buy a shirt and hat annually) and unique gifts

New outpost for beautiful art, jewelry, candles, and clothing

Curated collection of ethically-made goods from global artisans and heritage brands, featuring apparel, accessories, jewelry, bedding and linens, tabletop and home décor

Annual stop for charm bracelet additions

Stylish curation of clothing, home goods, and other functional objects from all over the world

Savor the Island’s Flavor

My favorite fish sandwich, fried seafood pints and quarts (love their oysters), and great pizzas

Hot or cold lobster rolls (top 3 on island), fried seafood, fresh fish market

Hot or cold lobster rolls (top 3), hot dogs and fries, burgers are to die for

Hot or cold lobster rolls (top 3), fresh sushi, and great ocean views

Popular town center outpost with great seafood and dock views

My reward after biking from Oak Bluffs to Edgartown: great seafood and beautiful harbor views

Call your lobster order in by 1pm before heading to Mnemsha for famous views of the sunset

Pancakes, breakfast biscuits, shrimp and grits, chicken & waffles are legendary

Simply the best breakfast in the world, and try as soon as they open or right before they close

If you know, you know, and you only live once! Buy and freeze apple fritters to take home!

Dinner Spots We Love

Delicious upscale menu in laid back lovely space (+beautiful sunset water views)

Favorite upscale burger on the island, mouth-watering menu, great wine list

Expanded due to popular demand and fun with good food

Beautiful upscale 5-star dining upstairs and in the gorgeous patio, and mouthwatering burger menu, sexy bar and DJ in the cellar.

Bistro and bar where island traditions meet city sophistication

Raw bar, kitchen and cocktails with live music on weekends

Soulful African Diaspora kitchen with brunch beats, Chef’s Table dinners, and community vibes on Martha’s Vineyard