Many first-time visitors to Chilmark compare it to the rolling meadows and winding lanes of Britain, but to those of us who live here, Chilmark's beauty stands apart. No visit to the Island can be complete without a driving tour through Chilmark, where unparalleled vistas greet you at every turn - from the view of South Mountain and the Atlantic across the Allen Farm sheep fields, to the breathtaking site of Nashaquitsa and Menemsha Ponds spreading out below you from the Quitsa overlook.
On that driving tour, you will want to stop at the Allen Sheep Farm on South Road to admire the beautiful woolens loomed from the sheep grown on the farm. In Beetlebung Corner, the town center, is our community center which bustles with activity all summer long – from camp programs for children every morning to lecture and film series in the evenings. Also in the center is our newly renovated and enlarged public library, the Chilmark Elementary School, our historic Town Hall and, of course, the Chilmark Store, where you will stop for a cold drink, suntan lotion and maybe even lunch to enjoy on the covered porch. If you stay on State (South) Road, drive slowly so that you don’t miss the Menemsha Schoolhouse on your right. Generations of Chilmarkers studied in this two-room schoolhouse, which is now the police station. Just beyond is Chilmark Chocolates! No visit to the Island will be complete without a sample of their yummy fare. From here the road will dip and climb – low across the Quitsa Bridge (don’t miss Stonewall Pond to the left) and then climbing up until you reach the overlook. Be sure to stop and really enjoy this view before driving on to Aquinnah.
On your way back “down-Island”, turn left at Beetlebung Corner and take the Menemsha Crossroad. Look for the beautiful Methodist Church on your right. Left again on North Road will take you to the fishing village of Menemsha. You will want to park and walk about Dutchers Dock and around to the Coastguard Pier. On the way, stop at The Galley for an ice cream. If it is late in the day, get a backdoor dinner from the Homeport Restaurant and watch the sunset – or plan ahead and make a reservation at the Beach Plum Inn where you will enjoy a lovely dinner looking out at the sea. If you have daylight to spare, there are many Martha’s Vineyard Land Bank properties that you can visit on your way east on either North or Middle Roads. Look for the green signs with white lettering. Each of these properties has been purchased through a transfer fee on properties sold here and are held as open, public space in perpetuity. There are well-marked walking trails at each property and each is uniquely different. The Land Bank owns and maintains thousands of acres across the Island. An alternative route down-Island from Beetlebung Corner is Middle Road, with its vistas over the Keith Farm to the Atlantic. Middle Road is thought by many to be one of the loveliest and most unspoiled roadways on the Island.