🌿 RelaxedWeekend · from Boston, MA
Martha's Vineyard: Island Villages & Gay Head Cliffs
Martha's Vineyard is accessible only by ferry from Woods Hole — a 45-minute crossing to an island that has maintained a distinct culture despite decades of celebrity association. The Aquinnah Cliffs at the island's western tip are 150-foot polychrome clay formations, sacred to the Wampanoag Tribe; the village of Edgartown preserves the whaling-era Federal architecture intact; Menemsha is the working-class fishing village that served as the filming location for Jaws.
Day 1 — Edgartown, MADay 2 — Aquinnah & Menemsha, MA
Day 1 — Edgartown, MA
Day 1 — Edgartown, MA
🚗 1 hr 30 min driving📍 6 stops
🌅
Morning
🚗
Drive
Boston, MA → Woods Hole Ferry Terminal
1 hr 30 min8:00 AM → 9:30 AM
Martha's Vineyard Ferry — Edgartown
★ 4.6The Steamship Authority ferry from Woods Hole takes 45 minutes to Vineyard Haven; from there, a 30-minute bus ride reaches Edgartown, the island's Federal-era whaling capital. The ferry carries vehicles; foot passengers have the same bus access. The Edgartown waterfront and the adjacent Chappaquiddick Island are accessible without a car.
9:30 AM📍 See location
🍽️
Lunch
Edgartown Historic District
The most intact Federal-era whaling port in New England — a dozen Greek Revival captains' houses on North Water Street, a working lighthouse on the harbor point, and the 1843 Whaling Church (now a performing arts center) on Main Street. The Martha's Vineyard Museum in the 1845 Thomas Cooke House traces the island's whaling history through logs, charts, and scrimshaw.
10:30 AM📍 See location
The Newes from America Pub
★ 4.4Edgartown's oldest tavern in a 1742 building that has served as a pub continuously for 280 years, with a menu of New England pub food — chowder, lobster rolls, fish and chips — and an extensive New England craft beer selection. The low-ceilinged rooms and wide-plank floors are original to the 18th-century building.
11:30 AM📍 See location
☀️
Afternoon
Edgartown Lighthouse & Harbor Walk
★ 4.7The 1939 cast-iron lighthouse at the Edgartown Harbor entrance is accessible via a 200-foot footbridge causeway from the town beach — the view from the gallery encompasses the entire Edgartown Harbor, Chappaquiddick Island, and the Nantucket Sound opening south. The harbor walk connects the lighthouse to the main street through the waterfront park.
12:30 PM📍 See location
🌙
Evening
Among the Flowers Cafe
★ 4.5A Edgartown institution since 1978, serving breakfast and dinner in a cottage garden setting behind the main street. The dinner menu features Martha's Vineyard farm produce and local seafood; the sunset light through the garden makes it the island's most atmospheric evening option.
5:00 PM📍 See location
🛏️
Charlotte Inn
A 19th-century mansion compound on South Summer Street in Edgartown, with the most attentive service on the island. The inn's English garden, art gallery, and Edgartown's walkable historic district make it the most civilized base on the Vineyard.
Day 2 — Aquinnah & Menemsha, MA
Day 2 — Aquinnah & Menemsha, MA
🚗 2 hr 37 min driving📍 4 stops
🌅
Morning
🚗
Drive
Edgartown, MA → Aquinnah Cliffs
30 min8:00 AM → 8:30 AM
Aquinnah Cliffs — Gay Head Light
★ 4.8The 150-foot polychrome clay cliffs at the Vineyard's western tip are a National Natural Landmark and sacred land of the Wampanoag Tribe — the layered strata of red, orange, black, and white clay were formed 100 million years ago and exposed by glacial action 12,000 years ago. The 1844 Gay Head Lighthouse at the cliff's edge was moved 135 feet from the eroding cliff edge in 2015. The beach below the cliffs is accessible by a steep trail.
8:30 AM📍 See location
🍽️
Lunch
🚗
Drive
Aquinnah Cliffs → Menemsha, MA
15 min9:30 AM → 9:45 AM
Larsen's Fish Market
★ 4.6A working fish market on Menemsha Harbor that has sold lobsters, steamer clams, and fish directly from the lobster boats since 1969 — the setting for the Quint's fish market scenes in Jaws. The harbor is still a working fishing village; wooden lobster traps are stacked on the dock, and the charter boats depart at 5 AM. Eat at the picnic tables facing the harbor.
9:45 AM📍 See location
☀️
Afternoon
Cedar Tree Neck Sanctuary
★ 4.9A 300-acre wildlife sanctuary in the island's interior with 2.5 miles of trail through pitch pine, scrub oak, and a freshwater pond before reaching a bluff above the Vineyard Sound with views to the Elizabeth Islands. The sanctuary is managed by the Sheriff's Meadow Foundation; the neck's undeveloped shoreline is one of the last undisturbed stretches on the island's north shore.
12:00 PM📍 See location
🌙
Evening
🍽️ Dinner5:00 PM
The Black Dog Tavern
A Vineyard Haven institution since 1971, The Black Dog Tavern serves chowder, fish and chips, and grilled swordfish in a cozy nautical dining room steps from the Vineyard Haven ferry dock. One of Martha's Vineyard's most recognizable names, and a fitting final stop before the Woods Hole crossing.
4 options · tap to switch
🚗
Drive
Menemsha, MA → Woods Hole Ferry Terminal
22 min6:00 PM → 6:22 PM
🚗
Drive
Woods Hole, MA → Boston, MA
1 hr 30 min6:22 PM → 7:52 PM
Return via US-6 east and I-95 south through Providence.
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