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Discover the Quiet Charm of Winter: Travel Tips for Visiting Martha’s Vineyard

Blog #60 Featherstone in WInter Time (PC Marnely)

When people ask if Martha’s Vineyard is worth visiting in the winter, the answer is always a resounding yes! The island may be quieter during the colder months, but this is when its peaceful charm truly shines. Winter on Martha’s Vineyard offers a unique experience: uncrowded beaches, cozy accommodations, and opportunities to connect with friendly locals. Plus, visiting during the off-season means better rates, exclusive access to coveted spots, and a more relaxed pace. Here’s your ultimate guide to planning a magical winter getaway to Martha’s Vineyard.

Getting to Martha’s Vineyard in Winter

Traveling to Martha’s Vineyard in the winter is convenient and often less hectic than during peak summer months. Here are your options:

By Ferry: The Steamship Authority operates year-round, with multiple daily trips between Woods Hole and Vineyard Haven. For those walking onto the ferry, park at one of the Steamship Authority’s designated lots, which includes a complimentary shuttle service to the terminal. Parking costs $10 per day through March, and passenger tickets are $10 each way. If you plan to bring a car, make reservations in advance—winter rates are often discounted, making this a budget-friendly option.

By Bus: Peter Pan Bus Lines provides direct routes to Woods Hole from Boston and other locations. Their user-friendly app allows you to book tickets in advance, making it a convenient choice for car-free travelers. Another bus option is Plymouth & Brockton, with daily bus service to and from Cape Cod, the South Shore, Logan Airport, Woods Hole, Falmouth, Provincetown, and Downtown Boston.

By Air: Cape Air operates year-round flights from Boston, Nantucket, and Westchester County to Martha's Vineyard Airport. Flying offers breathtaking aerial views of the island and is the quickest way to arrive.

Where to Stay

Winter visitors to Martha’s Vineyard will find plenty of cozy lodging options that remain open year-round, each offering warm hospitality and excellent amenities.

Mansion House (Vineyard Haven): Located just steps from the ferry terminal, Mansion House provides convenience and comfort with a variety of rooms and suites. Guests can enjoy the on-site fitness center, spa, and indoor pool—perfect for a relaxing winter retreat.

Harbor View Hotel (Edgartown): Overlooking the Edgartown Lighthouse, this luxury hotel combines elegance with prime access to local galleries, boutiques, and dining. The Harbor View Hotel’s beautiful amenities and charming setting make it a top choice.

Vineyard Square Hotel and Suites (Edgartown): Offering boutique accommodations in the heart of Edgartown, this hotel is an excellent option for travelers seeking charm and convenience.

Nobnocket Boutique Inn (Vineyard Haven): The Nobnocket Boutique Inn is a luxurious and contemporary bed-and-breakfast in Vineyard Haven on Martha’s Vineyard. Nestled in a peaceful setting just minutes from the ferry terminal, the inn offers an elegant blend of modern design and classic New England charm. 

For a complete list of year-round accommodations, visit the island's hotel directory to find your ideal winter escape.

Getting Around the Island

Even in winter, Martha’s Vineyard remains easy to navigate. Here’s how to get around:

Vineyard Transit Authority  (VTA): The island’s reliable bus system connects all six towns and runs year-round. Purchase a 1-day, 3-day, or 1-week pass for unlimited travel. Buses are equipped with bike racks and are handicap accessible.

Taxis and Uber: Local cab companies like Lighthouse Taxi and Stagecoach Taxi operate year-round, and Uber is also available. Taxis are often stationed at the Steamship Authority terminal in Vineyard Haven for easy access.

Car Rentals: Hertz offers car rentals at Martha’s Vineyard Airport throughout the year, ideal for visitors who prefer driving.

Things to Do in Winter

Despite the seasonal closures of some businesses, there are still plenty of activities to enjoy on Martha’s Vineyard during the winter months.

Arts & Entertainment: Featherstone Center for the Arts hosts year-round classes, exhibits, and events, making it a hub for creativity. Movie lovers can catch the latest blockbusters at Edgartown Cinema or enjoy indie films at the Martha's Vineyard Film Center.

Outdoor Adventures: The island’s conservation lands and trails remain open year-round, offering a serene setting for hiking and exploration. Popular trails like Menemsha Hills and Long Point Wildlife Refuge are particularly stunning in the crisp winter air. Download the TrailsMV app for a detailed map of trails across the island.

Dining: Winter is a great time to savor the Vineyard’s culinary scene. Many year-round restaurants offer cozy atmospheres and seasonal menus. Be sure to check out some of the year-round favorites including:

Holiday Magic on Island in December

Christmas in Edgartown is a cherished holiday tradition on Martha’s Vineyard, bringing festive charm to the island with a series of seasonal events and celebrations. Held annually in early December, this beloved weekend-long festival transforms the picturesque town of Edgartown into a winter wonderland, complete with twinkling lights and beautifully decorated storefronts. Highlights include the iconic Christmas parade, a holiday stroll through the town’s quaint streets, and the lighting of the Edgartown Lighthouse. Visitors can enjoy caroling, craft fairs, holiday-themed activities, and special sales from local shops and restaurants. Rooted in community spirit, the event also supports local charities, making it a heartwarming way to celebrate the holiday season. Whether you're a local or a visitor, Christmas in Edgartown captures the magic of the holidays with small-town charm and coastal beauty.

Tis the Season in Tisbury” is a festive celebration that transforms the charming town of Vineyard Haven on Martha's Vineyard into a magical holiday wonderland. Held annually in early December, this event invites locals and visitors alike to revel in the holiday spirit with a variety of family-friendly activities. The streets of Tisbury come alive with twinkling lights, carolers, and decorated storefronts, creating a warm and inviting atmosphere. Highlights include a holiday stroll, where guests can enjoy live music, shop for unique gifts from local artisans, and indulge in seasonal treats like hot cocoa and freshly baked goods. Santa often makes an appearance, adding to the festive cheer, while community traditions such as tree lightings at the Black Dog Tavern and a Giving Tree Lighting and special performances enrich the experience. For travelers, it’s a perfect opportunity to immerse yourself in the Vineyard’s close-knit community charm while kicking off the holiday season in style.

Light Up Oak Bluffs” is a beloved holiday event that brings the vibrant seaside town of Oak Bluffs on Martha's Vineyard to life with festive cheer. Typically held in early December, this annual celebration features the official lighting of the town’s holiday decorations, including a dazzling Christmas tree and colorful displays throughout the streets. The event offers a cozy and joyous atmosphere, with carolers spreading holiday melodies in Healy Square, local shops hosting open houses with special deals, and food vendors serving seasonal treats like hot cider and cookies. Families can enjoy activities such as ornament-making and visits with Santa, creating magical memories for children. For travelers, “Light Up Oak Bluffs” is a heartwarming way to experience the island's unique blend of community spirit and holiday magic, making it an unforgettable seasonal highlight.

Why Visit Martha’s Vineyard in Winter?

A winter trip to Martha’s Vineyard offers tranquility, charm, and unique experiences that are hard to replicate during the busy summer months. Without the crowds, you can truly connect with the island’s natural beauty, explore its vibrant arts scene, and enjoy authentic interactions with locals. Whether you’re seeking outdoor adventures, delicious dining, or a peaceful retreat, Martha’s Vineyard in winter is an unforgettable destination.

So pack your bags, bundle up, and discover the magic of Martha’s Vineyard this winter. It’s a getaway you’ll cherish for years to come.

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