Vineyard Haven Vs Oak Bluffs: Which Martha’S Vineyard Town Is Better?

Martha’s Vineyard is home to some charming and vibrant towns, each with its own unique character and appeal. If you’re trying to decide whether to base yourself in Vineyard Haven or Oak Bluffs during your Martha’s Vineyard vacation, this comprehensive guide will help you choose.

If you don’t have time to read the full article, here’s the short answer: Vineyard Haven is better for those looking for a quieter retreat in walkable natural surroundings, while vibrant Oak Bluffs suits travelers seeking fun attractions, dining and nightlife.

Locations and Accessibility

Vineyard Haven Location Overview

Vineyard Haven is a picturesque town located on the northeastern coast of Martha’s Vineyard. It is nestled between the towns of West Tisbury and Oak Bluffs. With its charming harbor and beautiful waterfront views, Vineyard Haven offers a serene and peaceful atmosphere for both locals and visitors alike.

The town is known for its historic Main Street, lined with quaint shops, restaurants, and art galleries, making it a popular destination for shopping and dining.

Oak Bluffs Location Overview

Oak Bluffs, on the other hand, is a vibrant and lively town situated on the northeastern tip of Martha’s Vineyard. It is known for its colorful Victorian-style houses, bustling downtown area, and the iconic Flying Horses Carousel.

Oak Bluffs is a hub of activity, with numerous entertainment options, including bars, clubs, and live music venues. The town also boasts beautiful beaches, such as Inkwell Beach, which attracts beachgoers and sun-seekers.

Getting to Each Town

Both Vineyard Haven and Oak Bluffs are easily accessible by various means of transportation. The most common way to reach Martha’s Vineyard is by ferry, with multiple ferry services operating from mainland Massachusetts.

The Steamship Authority provides year-round service to both Vineyard Haven and Oak Bluffs, making it convenient for visitors to choose their preferred town of arrival.

Additionally, for those who prefer to fly, Martha’s Vineyard has its own airport, located in the town of West Tisbury. Vineyard Haven and Oak Bluffs are both a short drive away from the airport, making it easy to reach either town after landing.

Once on the island, visitors can explore both towns by car, bike, or public transportation. Martha’s Vineyard Transit Authority operates bus services that connect Vineyard Haven and Oak Bluffs, as well as other towns on the island.

Biking is also a popular mode of transportation, with bike rental shops available in both towns.

Atmosphere and Ambience

When it comes to the atmosphere and ambience, both Vineyard Haven and Oak Bluffs offer unique vibes that attract visitors from all over. While Vineyard Haven boasts a relaxed and laid-back atmosphere, Oak Bluffs is known for its lively and energetic ambiance.

Vineyard Haven’s Relaxed Vibe

Vineyard Haven, located on the northeastern part of Martha’s Vineyard, exudes a tranquil and peaceful atmosphere. The town is known for its charming streets lined with historic houses and beautiful gardens.

Visitors can stroll through Main Street, where they will find a variety of boutique shops, art galleries, and cozy cafes. The pace of life in Vineyard Haven is slower, allowing visitors to unwind and enjoy the natural beauty of the island.

One of the highlights of Vineyard Haven is its picturesque harbor, which offers breathtaking views of the waterfront. Visitors can relax by the harbor, watch the boats sail by, or even take a leisurely cruise around the island.

The town’s relaxed vibe is perfect for those looking to escape the hustle and bustle of city life and immerse themselves in the serenity of Martha’s Vineyard.

Lively Oak Bluffs Atmosphere

On the other hand, Oak Bluffs is known for its vibrant and lively atmosphere. Located on the northeastern part of the island, Oak Bluffs is a popular destination for tourists seeking entertainment and excitement. The town is famous for its colorful Victorian cottages, which give it a unique charm.

One of the main attractions in Oak Bluffs is the Flying Horses Carousel, the oldest operating carousel in the United States. Visitors can take a ride on the beautifully restored carousel and feel a sense of nostalgia.

The town also offers a lively nightlife scene, with a variety of bars, restaurants, and live music venues.

Additionally, Oak Bluffs is home to the renowned Martha’s Vineyard Camp Meeting Association, famous for its charming gingerbread cottages. These cottages are a must-see attraction and add to the whimsical and festive atmosphere of the town.

Accommodation Options

Hotels, Inns and B&Bs in Vineyard Haven

When it comes to accommodation options in Vineyard Haven, visitors will be delighted by the variety of hotels, inns, and bed and breakfasts available. Whether you’re looking for a luxurious stay or a cozy and quaint experience, Vineyard Haven has something for everyone.

One popular option is the Harbor View Hotel, which offers stunning views of the harbor and elegant rooms with modern amenities. Another great choice is the Mansion House, a historic inn that offers a unique blend of old-world charm and contemporary comfort.

For those seeking a more intimate experience, there are also several charming bed and breakfasts scattered throughout the town.

Vineyard Haven’s accommodation options cater to a range of budgets and preferences, ensuring that every visitor can find a place to stay that suits their needs. With its charming accommodations and picturesque surroundings, Vineyard Haven is a wonderful choice for those looking for a tranquil and relaxing getaway.

Oak Bluffs Accommodation Choices

Oak Bluffs is another popular town on Martha’s Vineyard that offers a wide range of accommodation choices. From luxury resorts to cozy cottages, Oak Bluffs has something to suit every traveler’s taste.

One notable option is the Winnetu Oceanside Resort, which is located just steps away from the beach and offers spacious suites and cottages with breathtaking ocean views. Another popular choice is the Wesley Hotel, a charming inn known for its friendly staff and cozy rooms.

In addition to hotels and inns, Oak Bluffs also offers a variety of vacation rentals and guesthouses, perfect for those looking for a more independent and private stay. These options provide visitors with the flexibility to create their own itinerary and enjoy their vacation at their own pace.

Dining and Nightlife Scenes

Vineyard Haven’s Dining Options

Vineyard Haven, located on the northeastern coast of Martha’s Vineyard, offers a diverse range of dining options that cater to various tastes and preferences. From cozy cafes to upscale restaurants, this charming town has something for everyone.

One popular eatery in Vineyard Haven is The Black Dog Tavern, known for its delicious seafood dishes and waterfront dining experience. Visitors can savor mouthwatering lobster rolls while enjoying breathtaking views of the harbor.

Another must-visit spot is Waterside Market, which offers a delightful selection of fresh sandwiches, salads, and artisanal products.

For those seeking a more casual dining experience, look no further than the ArtCliff Diner. With its retro vibe and mouthwatering comfort food, this local favorite never disappoints. And if you’re in the mood for some international flavors, Thai Cuisine is a fantastic choice, serving up authentic Thai dishes that will transport your taste buds straight to Thailand.

Oak Bluffs: Fun Dining and Nightlife

When it comes to dining and nightlife, Oak Bluffs on Martha’s Vineyard is a hub of excitement and entertainment. This vibrant town offers a plethora of options for food enthusiasts and night owls alike.

One of the standout dining spots in Oak Bluffs is the Martha’s Vineyard Chowder Company, where you can indulge in a hearty bowl of chowder or feast on fresh seafood dishes. If you’re in the mood for some Italian cuisine, Giordano’s Restaurant is a fantastic choice, known for its delicious pasta dishes and cozy atmosphere.

After a satisfying meal, Oak Bluffs comes alive with its lively nightlife scene. The Ritz Cafe is a popular gathering spot, offering live music performances and a wide selection of craft beers. For a more laid-back vibe, head to the Lookout Tavern, where you can enjoy a refreshing cocktail while taking in stunning views of the harbor.

Whether you’re looking for a fine dining experience or a night out on the town, Oak Bluffs has plenty to offer, ensuring that you’ll never be bored during your visit.

For more information on dining options in Vineyard Haven, visit

Things to Do and Attractions

Activities and Sights in Vineyard Haven

Vineyard Haven, located on the northeastern coast of Martha’s Vineyard, offers visitors a charming and laid-back atmosphere with a variety of activities to enjoy. One of the must-visit attractions is the Martha’s Vineyard Museum, where visitors can learn about the island’s rich history and culture.

Take a stroll along Main Street and explore the unique shops, art galleries, and boutiques that offer a wide range of handmade crafts and locally sourced products. For nature lovers, a visit to Owen Park is a must.

This beautiful waterfront park offers stunning views of the harbor and the perfect spot for a picnic or a relaxing walk. Don’t forget to check out the Vineyard Haven Public Library, which hosts various cultural events and exhibits throughout the year.

Top Oak Bluffs Attractions and Entertainment

Oak Bluffs, located on the northeastern tip of Martha’s Vineyard, is known for its vibrant and lively atmosphere. One of the most popular attractions in Oak Bluffs is the Flying Horses Carousel, the nation’s oldest operating platform carousel.

Step back in time and enjoy a ride on one of the beautifully hand-carved horses. The picturesque Oak Bluffs Harbor is another must-visit spot, offering breathtaking views of the boats and the charming Gingerbread Cottages.

These colorful and intricately designed cottages are a unique sight to behold and are a testament to the town’s rich history. For those looking for entertainment, the Martha’s Vineyard Film Center in Oak Bluffs showcases a variety of independent and international films.

Additionally, the town is known for its vibrant nightlife, with a host of bars, restaurants, and live music venues offering a lively atmosphere for visitors to enjoy.


Both Vineyard Haven and Oak Bluffs have distinct atmospheres and their own unique attractions that make them delightful home bases for exploring Martha’s Vineyard.

For a relaxed retreat surrounded by nature, Vineyard Haven is the best fit. Meanwhile, visitors looking for vibrant nightlife, attractions and dining will prefer lively Oak Bluffs.

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