It doesn’t matter how many years you’ve lived on Martha’s Vineyard, unless you’re born there, you’re a “wash ashore.”

The island off the New England state of Massachusetts occupies 100 square miles of rugged coastline.   And while cars aren’t banned, bikes are encouraged, with paths criss-crossing the towns “up-island” and “down-island.”

The more rural towns to the west are “up,” while the more populous towns in the east are “down.”

Martha’s Vineyard IS Main Street, USA.  The ever-present stripes and stars weren’t just a nod to President Obama, who was among the most famous guests on the island when I visited.  This is the sort of place depicted in classic scenes from America; white picket fences, flags swaying above front porches and chairs rocking while the sun sets over the Vineyard Sound.

We took a fast, one-hour ferry from New Bedford, Massachusetts, but there are several options, including flights and ferries from New York.  If all you’ve got is a couple of days, it’ll be plenty to get a feel for things, but a week would be perfect, especially if you’re the outdoorsy type.

Our boat arrived at Oak Bluffs, the busiest town on the island, and, admittedly, my favourite for its ease of use (read: choice).  Busy on the Vineyard is different from busy anywhere else.  Most of the Vineyard’s bigger towns can be walked about in roughly an hour, so nothing is terribly overwhelming.  And Oak Bluffs is rich with history.  It attracted Methodists in the 19^th century, who created a charming area known as “The Campground,” an enclave of winding streets, lined with gingerbread cottages, each one decorated with ornate mouldings and bright colours, with different themes.  They are captivating, cherished landmarks, handed down from generation to generation.

Most have heard lots about the Kennedy’s history on the Vineyard, and the Clintons visits, but Oak Bluffs, in particular, has an interesting African-American history.  A long line of affluent Black Americans (does the name Spike Lee ring any bells?) preceded Obama on the island.  White locals sold land to freed slaves, laborers and sailors, mostly from Boston, in the 18^th century, paving the way for middle-class blacks to continue the trend, buying or renting summer homes in the 19^th and 20^th centuries.  Descendants return to the island annually and many live here year-round.    The local beach has even earned the nickname, “Inkwell.”  This background, and diversity, make the island far more fascinating than many of New England’s traditionally homogeneous coastal towns.    For those who want to dig deeper, there are tours and trails exploring the African-American past.

An efficient bus system moves people around the island easily, though I’m told the best beaches are difficult to access without a bicycle or a car.   Boats can be chartered, but if you want to keep up your fitness levels, kayaking is the way to go.  Chick Dowd has been running Island Spirit Kayaks, on the edge of Oak Bluffs, for years, and recently paddled out with the Obama family.

I figured if it was good enough for them, it’d be good enough for me.  The kayak shack is located right near a bus stop, and there are tours at sunrise, sunset, mornings and afternoons.  The 2 1/2  hour tour seemed just right for me.  I lucked out with just one other person on my tour, and a terrific guide named Phil, who kept an eye out to make sure neither of us were carried too far out.    Tours are catered for beginners, novices, and more experienced paddlers.  We were treated to a beach break, with snacks, and a lovely walk down a deserted stretch of sand where we collected shells and compared sea glass.   Phil grew up spending summers on the Vineyard, and became more of an unofficial island guide, giving interesting background about the island and its residents, in addition to terrific tips for staying afloat, even in a stronger current.   The kayak tour was a real highlight, and a different way to view the island.

Five working lighthouses look out over the Vineyard and Nantucket sounds and you could spend a couple of hours exploring each one.

We stayed in Edgartown, a small town six miles from Oak Bluffs.  It was quaint, and delightful, if a little removed from the action.   Restaurants have been called both “expensive and unimpressive” and I have to agree.  Oak Bluffs offered the best dining options.  There are plenty of upscale, boutique hotels, but we stayed at The Edgartown Inn, one of just two remaining historical and traditional inns in Edgartown.   Built in the late 18^th century, it has hosted Nathaniel Hawthorne and JFK throughout its time.    The inn is less than a 5-minute walk into town, and evenings were spent reading on the front porch, to the sounds of a bluegrass band playing on the lawn next door.   It’s a place where one can find it quite easy to slow down.

If you’ve got some time to spare from a home base in New York, or southern New England, spend a few days washed ashore.

Ferry:

www.seastreak.com

Kayaks:

www.islandsspirit.com

Accommodation:

www.edgartowninn.com

www.mvol.com