From lighthouses to lawn chairs, beaches to bungalows, Martha’s Vineyard oozes with historic charm.  There’s a bit of everything on this large Massachusetts island that is a summer and fall resort for so many New England families.

For many, it’s simply the climate and the beaches.  It will be ten degrees cooler here than in Boston or New York City during a hot summer’s day. Yet, the waters are warm enough to swim – about the temperature you’ll find further south in Virginia.  If the crashing waves on the south or ocean side are not to your liking, there’s much calmer bays that are much smoother.

Unique Charms

Plus, there’s the charm of huge guest houses, tiny bungalows, full-service inns, parks with gazebos, and unique historic architecture.

For example, the nation’s oldest carousel is found here inside of a wooden building.  It may be small, but judging from the lines of children, it was as popular as any Disney ride.

Then, there’s Wesleyan Grove, 34 acres of gingerbread cottages run by the Martha’s Vineyard Camp Meeting Association. It’s the site of the nation’s first Christian summer camp and in the midst of the cottages lies a huge, 2,000 seat open-air tabernacle where revival meetings were held in the late 1800’s and early 1900’s.  

Both the tabernacle and the cottages have been remarkably preserved as a part of the Oak Grove community. You can take a tour of one of the cottages, attend an evening concert, and, if you’re lucky, go to a special event like the children’s Fourth of July parade. 

Picture Perfect Plus Activities

Moving back to the water, around every corner is a captivating scene worthy of a photo. There are coves and harbors full of every type of watercraft imaginable – plus jetties with fishermen and peculiar car ferries and even a ferry for bicycles.

For rainy days, there’s the Martha’s Vineyard Museum in Tisbury housing an old Fresnel (lighthouse) lens with a spectacular harbor view (see cover photo). Exhibits center on the whaling and fishing past along with hurricanes and winter storms that wreaked havoc.

For shopping, there’s tony Edgartown with it’s colonial style architecture and specialty shops.  Come early in the day because of narrow streets and restricted parking.

Outside of Edgartown, there’s an old grass field aerodrome (Katama Airfield) where visitors can climb aboard a Red Baron style biplane. Even if you’re not up for a flightseeing tour, you can watch their takeoffs at an adjacent diner.

Inland, Martha’s Vineyard turns rural with vineyards and sheep farms.  There’s a few places here that are tourist worthy such as the Polly Hill Arboretum, the Island Alpaca Company, and the Field Gallery and Sculpture Garden. The flower filled arboretum highlights landscape architecture in a natural setting. Island Alpaca is a farm where the kids get in the act of helping to groom and feed the animals – plus they sell quality Alpaca knits.


At the far west end of the island is Gay Head light sitting atop an eroded bluff with a panoramic view of the sea. There’s some adjacent craft shops and eateries that are worth a look.  However, parking is timed and somewhat limited.

Important Travel Tips

But with everything going in its favor, this favorite island getaway is hardly known to those south of New York.  And, there’s some good reasons why.

The peak summer season, from late June through Labor Day, is crazy crowded and expensive.  One of my New England friends told me I was “brave to attempt going there then”.  Indeed, hotel reservations in January were filling up for June. 


And it’s not just hotel rooms that sell out well in advance, it’s the transportation.  There are limited flights to the island, mostly out of New York and Boston. The other option is to take a car ferry from Woods Hole, Massachusetts or a passenger ferry from Rhode Island.  Even those are expensive and fill up well before summer.

Which brings me to a key point:  The best time of year to go is September (after Labor Day) to mid-October. The crowds vanish and the prices drop. Early September is usually still warm enough for a swim while you will see some fall foliage in mid-October. The spring season tends to be cool and foggy and these conditions can last well into June.

There are two ways I’d suggest a visit.  First, do your own fly-drive vacation. You could plan a side trip to Nantucket for a day or two since a ferry connects both places.

Second, small boat cruises in the fall stop here as a port-of-call. These cruises often start or end in Boston or New York and combine Martha’s Vineyard with places like Provincetown, Boothbay Harbor, Maine, and Bar Harbor, Maine.

Regardless, if New England is on your bucket list of travel destinations, I’d be privileged to help you plan a vacation there.