Martha’s Vineyard: An End of Summer Daytrip from Cape Cod

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We treated ourselves to a “farewell to summer” trip to Martha’s Vineyard the other day, much like we greeted the summer with a daytrip to Nantucket in the spring. After a wonderful season of warm weather, bright sunshine, and our inn full of guests from near and far, we enlisted the help of our innsitter for a day and set sail for the island via the Island Queen ferry out of Falmouth Harbor.

We took the 9:00 AM ferry, along with a few other early birds, and landed in Oak Bluffs less than 45 minutes later. Looking to circumnavigate the entire island in a day, we opted to rent a mini-Cooper convertible and enjoy the late summer sunshine in style. We drove towards Edgartown via the Beach Road as soon as all the paperwork for the rental was complete, but instead of going into town, which we had done on many previous excursions to the island, we took the Katama Road to South Beach. The beach was just beginning to fill for the day with late summer sun worshippers eager to hit the beach for a day that promised wall-to-wall sunshine. On any other day we would have opted to join them, but our mission was to see as much of the island as we possibly could so that we could advise our guests of the best things to see and do on a day trip to the island.

Our route took us past the airport via the Edgartown-West Tisbury Road and down towards Aquinnah and Gay Head via the South Road. Martha’s Vineyard is extremely rural and lush with farms and fields, as well as wooded areas of scrub oak and pine. Many dirt roads and long winding drives branched out from the main roads, leading I assume to lovely waterfront estates and secluded beaches. But without a local guide to point the way to the Vineyard’s hidden treasures, we were left with just a rudimentary map of the island to navigate our course to the east end of the island.

The view from the lighthouse at Gay Head is absolutely inspirational–sparkling sea and dramatic heath-covered cliffs that lead to secluded sandy beaches. However, the walkway to the scenic overlook is lined with concessioners selling everything from fast food to tee shirts. It is a stark contrast betwixt inveterate commercialism and stunning natural beauty. I chose not to let the blur of tacky tourist traps mar my experience and simply drank in the vista before me: all blue sky and an ocean of next to navy in color lined with dramatic cliffs of golden sand. It reminded me in many ways of the Greek islands and the Mediterranean Sea.

We lingered only a short while before retracing our steps to the tiny fishing village of Menemsha. Our plan was to have lunch at either The Bite or Larsen’s, as their reputation for fresh seafood is of near historic proportions around these parts. Unfortunately, The Bite was closed on the Tuesday we visited, and Larsen’s menu was limited to steamed shellfish, which didn’t suit my husband’s penchant for all things fried. So we pressed on, eventually landing in Vineyard Haven where we dined at the infamous Black Dog Tavern while watching the boats bobbing in the harbor. After a good, but unremarkable lunch, we shopped a bit for the logo sportswear that has become world famous at the eponymous gift shop next door.

We ended the day as it began, with a return drive to Oak Bluffs, past the lighthouses of both East and West Chop, a quick spin through the gingerbread cottages on the grounds of the Martha’s Vineyard Camp Meeting Association, and a peek at the Flying Horses Carousel, the nation’s oldest operating platform carousel and a National Historic Landmark.

The ferry trip back to the mainland was uneventful, and as we exited the parking lot to start our journey home to the Inn, we were filled with a sense of anticipation at what the fall would bring and an overwhelming gratitude for this wonderful region we call home.