Once the site of a major whaling station, Vineyard Haven Harbor is a popular destination for summer vacationers and year-round adventurers. The Martha's Vineyard Seafaring Center in Vineyard Haven Harbor is a popular museum that exhibits historic maritime artifacts. There are also many opportunities for biking and hiking on the island.

Vineyard Haven Harbor has a humid continental climate with huge temperature differences from season to season. Summers can be hot and humid, and winters can be very cold. Precipitation is fairly evenly distributed throughout the year. Summer rain comes in thunderstorms and the occasional tropical system. The wettest month of the year is March, and the driest month is July. Temperatures range from an average high of 26°C (80°F) in July to an average low of -4°C (24°F) in January.

Vineyard Haven Harbor is home to many beautiful classic sailing vessels. Tisbury Wharf is a place to stop for a bite or some shopping where you can enjoy an old-fashioned wooden boatyard. Within a short walk from Vineyard Haven Harbor's Tisbury Wharf are beaches, theaters and other entertainment, shops, and restaurants.

Chicama Vineyards in Vineyard Haven Harbor offers free tours of its winery from May through October from 11am until 5pm (Monday-Saturday) and 1pm until 5pm (Sunday). It was the first bonded winery in the State of Massachusetts. This family-owned and -operated vineyard provides a main tasting room for wine sampling, and visitors are invited to walk through the vineyards that stretch to the surrounding forest.

The Martha's Vineyard Glassworks in Vineyard Haven Harbor makes high-quality and unique hand-blown glass created by master craftsmen while visitors watch the work. The studio was created for glassblowers to work daily, develop their skills, and create beautiful glasswork. Each beautiful piece available for sale in this Vineyard Haven Harbor glassworks is individually hand-blown by experienced artists.

The Long Point Wildlife Refuge Beach in the Vineyard Haven Harbor is open daily from 9am until 5pm. The refuge contains nature trails that travel from shore to forest to grassland. Containing over 600 acres, the Refuge Beach is one of the island's biggest publicly-accessible natural areas.

With beaches, dunes, woodlands, and sandplain heath, the Refuge in Vineyard Haven Harbor is popular in season and off season. Just over three kilometers (two miles) of easy-walking trails move through oak forest, open savanna, and beachfront. Open from mid-June through mid-September, this Vineyard Haven Harbor Refuge has public restrooms, picnic tables, bike racks, and a visitor center. Admission is $3 for adults. Parking is $9 per car. Children can enter free of charge.

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