Martha's Vineyard, MA
New England Islands
Gingerbread cottages, lighthouse cliffs, and the ferry ride is half the fun
Martha's Vineyard is 2.5 hours from Fairfield County plus a ferry — and it delivers exactly what you hope: gingerbread cottages painted in pastels at Oak Bluffs, dramatic red clay cliffs at Aquinnah, a working Flying Horses carousel that grandkids obsess over, and beaches of every character for every age. The Vineyard moves at exactly the right pace for grandparents and toddlers.
2.5 hrs drive to Woods Hole · 45 min ferry to Oak Bluffs or Vineyard Haven · No passport required
Why Grandparents Love It
The Vineyard has a well-maintained bike path network connecting all the main towns — rent bikes for any ability level
Every town is compact and walkable — Edgartown, Oak Bluffs, and Vineyard Haven each fit in a morning
The ferry ride from Woods Hole with grandkids is a memorable experience in itself — 45 minutes with views of Vineyard Sound
Flying Horses Carousel (Oak Bluffs): the oldest operating platform merry-go-round in the United States, 1876 — $3/ride
Aquinnah Cliffs: dramatic 150-foot red, orange, and white clay cliffs above the Atlantic — no charge to walk the path
The Gingerbread Cottages of Oak Bluffs: 300 Victorian Gothic cottages in every color in one of the country's oldest Methodist camp meeting grounds
Joseph Sylvia State Beach: a long, calm, warm lagoon beach perfect for young swimmers — free, on the bike path
Top Free Pick
Oak Bluffs Gingerbread Cottage Walk
Walk the Wesleyan Grove at the center of Oak Bluffs — 300 Victorian Gothic cottages painted in every possible color combination, each barely larger than a large room. Free to walk through the entire neighborhood. The Trinity Park Tabernacle, a massive iron open-air church at the center, hosts events all summer.
Top Activities (4)
Flying Horses Carousel
Ages 2–12 (height minimum for unassisted)The oldest surviving platform merry-go-round in America (1876), with hand-carved horses and glass eyes. Each horse has a real horse-hair tail. The brass ring tradition — reach out and grab rings from a dispenser as you pass — gives kids a reason to ride again and again.
Grandparent note: The carousel is in the center of Oak Bluffs circuit park — walk to it from the ferry dock in 5 minutes. It is the most charming carnival ride in New England.
Aquinnah Cliffs & Lighthouse
All agesThe far western tip of the island with 150-foot multicolored clay cliffs — red, orange, white, and ochre — above a dramatic beach. A lighthouse sits at the top. The Wampanoag Tribe of Gay Head has managed this land for centuries; their story is told at the interpretive center.
Grandparent note: The path from the parking area to the cliff viewpoint is a gentle 10-minute walk on paved and gravel surfaces. The beach below requires a steep (but short) descent — beautiful but not for all mobility levels. The view from the top is completely sufficient.
Joseph Sylvia State Beach
All agesA 2-mile barrier beach between Nantucket Sound and a warm saltwater lagoon. The lagoon side has calm, warm, shallow water — ideal for toddlers and nervous swimmers. The sound side has gentle waves. A bike path runs the entire length. Free with no reservation required.
Grandparent note: The lagoon side is the best bet for young grandkids — the water is bath-warm by July and stays calm in any wind. Arrive before 10am to park on the shoulder.
Edgartown Walking Tour
All agesThe most elegant town on the Vineyard — white captain's houses from the whaling era, a beautiful harbor, the Vineyard Museum, and Edgartown Harbor Light (1828). Walk from the center of town to the Memorial Wharf and back in an hour. Ferry to Chappaquiddick leaves from the wharf for $4 each way.
Grandparent note: Park on the outskirts of Edgartown and walk in — downtown parking is impossible in July. The town has exceptional ice cream at Edgartown Creamery and excellent lunch spots on Water Street.
Where to Stay
Harbor View Hotel (Edgartown)
Historic Hotel · $400–700/night
A Victorian grand hotel overlooking Edgartown Harbor — the most beautiful lodging on the island
Vacation Rental (VRBO)
Cottage · $250–600/night
Best for 4+ night stays — kitchen saves on the Vineyard's expensive restaurants, more space for grandkids
Where to Eat
Menemsha Fish Market
$$Seafood/Takeout
The best lobster and clam chowder on the island, eaten outside at picnic tables while watching fishing boats
The Black Dog Tavern (Vineyard Haven)
$$Casual
The Vineyard institution since 1971 — everyone gets the sweatshirt, the clam chowder is excellent
Offshore Ale Company (Oak Bluffs)
$$Pub
The Vineyard's best brewpub — the nachos are enormous, kids are welcome, casual and fun
Grandparent Tips
Book ferry reservations for your car 4–6 months ahead — the Steamship Authority fills completely in July and August
Consider going car-free: take the ferry as a foot passenger and rent bikes or use the VTA bus system on-island
September is the best month — the island empties after Labor Day, restaurants are less crowded, and it's still beautiful
The Vineyard has no Uber/Lyft — taxis and the VTA bus are the alternatives to renting a car
The bike path from Oak Bluffs to Edgartown (5 miles, completely flat) is the single best family activity on the island
Bring layers for evenings — even in July, Vineyard evenings can drop to 60°F
Sample Itinerary
Day 1 — Ferry & Oak Bluffs
Morning: Drive to Woods Hole, ferry to Oak Bluffs (45 min)
Afternoon: Gingerbread Cottage walk, Flying Horses Carousel
Evening: dinner in Oak Bluffs
Day 2 — Aquinnah & Beach
Morning: Drive to Aquinnah Cliffs (far west tip)
Midday: Menemsha Fish Market lunch — eat on the dock
Afternoon: Joseph Sylvia State Beach lagoon swim
Evening: Edgartown dinner
Day 3 — Edgartown & Ferry Home
Morning: Edgartown walking tour, Chappy Ferry side trip
Lunch: Water Street, Edgartown
Afternoon: Ferry from Vineyard Haven back to Woods Hole
Printable PDF Guide
A 2–5 page travel guide for Martha's Vineyard — formatted for printing or saving to your phone.
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