Martha’s Vineyard Vacations in the Off-Season

Avoid the crowds and visit this idyllic Cape Cod island in the fall or winter, instead.

Everyone knows it’s better to travel to popular vacation destinations in the off-season, but sometimes there’s just no point. Why visit a water park when it’s too cold to swim? Northern Florida beaches when it’s only 50 degrees Fahrenheit? Southeast Asia during the rainy season? No thanks. I’ll brave the crowds. But sometimes an off-season destination can transcend the weather and become even more special for those who look for it.

Martha’s Vineyard for me is one such place. Yes, in the summer there are beautiful beaches, outdoor dining and all sorts of warm-weather activities available—but it also can be a zoo. You’ll be cheek-by-jowl with people on the inter-island ferries during peak season, yet have rows of seats to yourself in the fall and winter. And, truthfully, every season on the island has its own beautiful aspect to discover. As a Boston resident, I’ve been visiting the island for more than 10 years in every kind of weather and have never been disappointed. I spend every New Year’s Eve there, which is as opposite of peak as it gets!

All About Martha

The 100-sq.-mile island has drawn visitors since at least the 1800s, and visiting celebrities and politicians such as the Kennedys and the Clintons have only made it more popular. A mere seven miles off the coast of Massachusetts, visitors arrive by ferry or plane. I usually take the ferry. In less than 45 minutes, I’ve left the “real” world behind with all my cares. While the island has several towns, day-trippers and weekend visitors usually gravitate to Oak Bluffs, Vineyard Haven and Edgartown, each with its own personality.

Oak Bluffs is home to hundreds of colorful 19th century “gingerbread” cottages (really tiny Victorian homes), built by Methodist church members who set up summer camps there in the 1800s. Vineyard Haven, the main ferry port, is by far the most touristy of the Island’s towns and is where you’ll find the world-renowned Black Dog Tavern. Edgartown, where most of the 19th century wealthy whaling captains lived, features stately mansions, toy shops and trendy restaurants.

Bargain Shopping and Insider’s Spots

A common misconception is that the island shuts down as soon as Labor Day is over. While some shops start to button up and maybe cut their hours, this is the time to find bargains as shopkeepers are eager to clear out inventory to prepare for next year. Some of the more touristy restaurants close their doors for the fall and winter months, but that means you’ll gravitate to local spots, often a better choice anyway.

Through late September, even into October, swimming can be wonderful—the water can be warmer than in July. And best of all, parking is a breeze. Felix Neck Wildlife Sanctuary has two miles of hiking trails to explore. Visit the observation building to look for wood ducks and other waterfowl.

Visit During a Festival

Plan a visit around one of the many annual festivals in the fall or winter. October 2008 welcomes the 5th Annual Vineyard Artisans Columbus Day Festival, which features artists working in leather crafts, glass, painting, ceramics, botanicals, sculpture and more in West Tisbury. Other Vineyard Artisans festivals include the Thanksgiving art show and the annual Labor Day Festival.

Sign up for the annual Columbus Day 5K Road Race and one mile Fun Run (and 5K Walk) on Oct. 12. It’s a gorgeous run around East Chop in Oak Bluffs and proceeds benefit the Island Affordable Housing Fund.

The popular Martha’s Vineyard Food & Wine Festival, Oct. 17 to 19 in Edgartown, is a three-day extravaganza of wine tastings, seminars and gourmet cuisine served up by local and world-renowned chefs.

From Dec. 12 to 14, the festive tradition of Christmas in Edgartown features a parade with the jolly man dressed in red, a chowder contest and a cookie-tasting contest, as well as art gallery openings and wine tastings. There’s even a Christmas Ball.

For more details, visit the Martha’s Vineyard Chamber of Commerce Web site,

Destinations: Martha’s Vineyard

Themes: Beach Vacations, Family Travel

Activities: Sightseeing, Wine Tasting