What to Do in Martha's Vineyard in the Offseason

{The Hob Knob Inn}

In all the times I've spent back east on the South Shore in Massachusetts, I had never ventured beyond Cape Cod. Last October, we decided to change that and booked a long-weekend stay on Martha's Vineyard. I loved the hotel we stayed at in Edgartown, The Hob Knob Inn, and we were lucky enough to be able to take advantage of the low-season prices.  They serve a lovely, delicious breakfast and afternoon tea/snacks (there's lemonade in the warm season).
Tip: If traveling by car to the island, you must buy/reserve your ticket in advance through Steamship Authority (well in advance if during the high season).
Where to stay: Hob Knob- a luxury boutique hotel in Edgartown- the main town on the island. Rates are steep during the high season (between Memorial Day Weekend and Labor Day Weekend.) Try booking an off-season stay.  Enjoy an afternoon on the porch with a glass of lemonade and an intriguing book.  
What to Do: Take a drive around the island for scenic views. Don't confine yourself to the picturesque yet touristy towns like Edgartown and Vineyard Haven. Wander into a local, independent bookstore and be charmed by the local authors, including a personal favorite, Susan Branch.  Be sure and check out Oak Bluffs and its beautiful "gingerbread" style homes.  Go off the beaten path and head towards a less inhabited part of the island- venture down to Aquinnah, a beautiful seaside village with a spectacular view, a historical lighthouse, and a bit of history to go along with it.
Where to Eat: Despite the well-to-do crowd of vacationers it attracts, Martha's Vineyard is unfortunately lacking in restaurant choices- both in terms of quality and variety.  Waterside Market in Vineyard Haven was one of the few places that satisfied- go there for lunch- they have a large soup and sandwich menu.

{Gingerbread-style architecture in Oak Bluffs}

{Ferry from Woods Hole, Cape Cod}

{Gay Head lighthouse in Aquinnah}