(Click on the map below to enlarge)   The western end of the Island consists of three rural towns: West Tisbury, Chilmark and Aquinnah. This part of the Vineyard is called "Up-Island" because as you travel west you move up the scale of longitude; the expression is a holdover from the days of seafarers.

Up-Island's beautiful vistas encompass the wildness of wind, tide and space. Ancient paths and structures inform the traveller of times when the Wampanoag Indians hunted for white-tailed deer and colonists farmed the land. South Road is in part the Indian footpath made before English settlement. The King's Highway established in colonial days still runs unpaved in places, offering ideal trails for horseback riding. Stone fences, protected by law, are reminiscent of the sheep farming prevalent during the 17th century.

1. Christiantown

The Indians called this place Mackkonnetchasqua, and it was included in the bounds of Christiantown, given by Sachem Josias in 1659. The Township was governed by the tribesmen under England's Society for the Propagation of the Gospel. Many of the Wampanoag Indians adopted Christianity through the ministry of Thomas Mayhew Jr., one of the original colonists. Indian graves here reflect both pagan and Christian beliefs. A tiny chapel, dating from 1828, still stands. The tribe bought the cemetery back from the county in recent years.

2. Liberty Oak Tree

When farming dominated the area, most trees were cleared, but this one was spared. Although it sustained major damage in 1993, the tree, with its massive, sagging limbs, is an Island landmark.

3. Town of West Tisbury

With the old general store, town hall, Congregational Church, Music Street, and Grange Hall all in a row, this town still typifies the old New England village. The name Music Street comes from whaling days when Capt. George A. Smith bought a piano — the first in town — for his daughter. Shortly thereafter, seven more pianos were purchased by his sea captain neighbors for their daughters.

4. Brookside Farm

Amid spectacular views of rolling hills, and lying between two ridges, this Middle Road farm is lined with stone fences. Brookside Farm is not open to the public.

5. Keith Farm

This farm off South Road offers a beautiful view of the Atlantic Ocean beyond its green, well-mowed fields. Cattle and horses walk near the barn, and Canada geese visit the lovely ponds. Keith Farm is not open to the public.

6. Menemsha Hills

Owned by The Trustees of Reservations, this nature walk boasts the highest elevation of any conservation area on the Island. From the top of the sandy bluffs to the rocky north shore below, a beautiful stroll.

7. Menemsha

With its lobster pots, nets, rigging and other gear used in Vineyard fishing, Menemsha is an artist's paradise. It is also a working fishing village; fishing boats dock and unload their catch here at fish markets.

8. Nashaquitsa Lookout

Stop here for a lovely view of Menemsha and Quitsa Ponds and the undulating shoreline, Chilmark woods and small craft spread out below. On a clear day, the Elizabeth Islands can be seen in the distance.

9. Aquinnah Spring

This water rises from an underground water source. All Island water comes from the rain that soaks the sand and soil. Hard clay underneath the sand channels the water to the surface in some places.

10. Gay Head Cliffs

Bartholomew Gosnold, who named the Island, called this colorful head of land Dover Cliffs, but British sailors preferred the name Gay Head. The sailors' name stuck. Steeped in natural history — covering millions of years — these Cliffs have yielded fossils of ancient flowers, sharks and camels. Gay Head Lighthouse stands like a sentry by the Cliffs. Descendants of the Wampanoag Indians still live in Aquinnah.

11. Old Mill Pond

Geese and swans munching bread crumbs by the pond or sauntering across the road are notorious for forcing cars to stop. The pond was called Factory Pond, back when the building next to it manufactured a local woolen material called satinet, used to make sailors' pea jackets.

12. Manuel F. Correllus State Forest

Centrally located and covering 5,100 acres, this forest is criss-crossed by fire trails — ideal for trekking. Paved bike paths stretch for miles amid plants, wildflowers and small birds. In 1908, part of the forest was set aside to protect the heath hen, but in 1916 a fire killed most of these birds on their nests; the last one died in 1933.

13. Grange Hall

The recently renovated Grange Hall still stands, and is the site of the Farmers' Market. But during 1994, legions of volunteers went to New Hampshire, dismantled a historic barn, brought it back to the Panhandle in West Tisbury, not far from the Grange Hall, and reassembled it as one of the Island's glories.

14. The Mayhew Monument/Place by the Wayside

On this spot Rev. Thomas Mayhew Jr. gave his last sermon to the Indians before leaving for England in 1647. His ship was lost at sea. The Indians honored his memory by placing a stone on the spot each time they passed by. Later, the pile was replaced with this monument which marks the location.