Sometimes, the best escapes from New York City don’t require a plane ticket or hours stuck in bumper-to-bumper I-95 traffic.
Tucked away off the coast of Massachusetts is a storybook destination that feels worlds away from Manhattan’s concrete canyons: Martha’s Vineyard’s Oak Bluffs Campground, a collection of more than 300 intricately detailed, pastel-painted Victorian “gingerbread” cottages that look like they were plucked straight from the pages of Hansel and Gretel.
Getting there depends entirely on the season. During the balmy summer months, you can hop on a direct high-speed ferry straight out of Midtown Manhattan. But if you’re looking for a crowd-free, cozy winter escape, the journey trades a boat cruise for a scenic train ride paired with a brief ferry crossing.

How to get there: Direct summer ferry vs. winter train-to-ferry connection
Your route to the Gingerbread Cottages depends on whether you’re traveling during peak beach season or bundle-up weather:
- In the summer (Direct Ferry): You can board a seasonal high-speed catamaran directly from Manhattan. The Seastreak Martha’s Vineyard Ferry runs select summer weekends between Memorial Day and Labor Day from the East 35th Street terminal. It sails along Long Island Sound and drops passengers right at the Oak Bluffs marina in about 4.5 to 5 hours.
- In the winter (Train + Connecting Ferry): The direct Manhattan ferry does not operate during November, December, or the winter months. To visit in the off-season, take an Amtrak Northeast Regional train from Moynihan Train Hall at Penn Station to Providence, RI, or Boston’s South Station. From there, transfer to a regional Peter Pan Bus down to Woods Hole on Cape Cod. At Woods Hole, walk onto the Steamship Authority Ferry, which runs daily, year-round sailings across Vineyard Sound (a quick 45-minute crossing, $11 one-way walk-on) directly into Vineyard Haven. Once you dock, Oak Bluffs is a quick 10-minute ride via cab or the local Vineyard Transit Authority (VTA) bus.

Exploring Martha’s Vineyard’s gingerbread village
Originally founded in 1835, the grounds quickly evolved in the late 19th century into a permanent enclave of Carpenter Gothic cottages. Today, 312 of these tightly clustered, candy-colored homes remain. Each boasts ornate architectural gingerbread trim, whimsical color palettes, and flower-filled porch boxes.
- The Tabernacle: The village centerpiece is an open-air, octagonal wrought-iron pavilion erected in 1879, which hosts community gatherings and seasonal summer concerts.
- The Cottage Museum: Located on Trinity Park, this preserved 19th-century cottage allows visitors to step back in time with vintage photographs, period furnishings, and historic island artifacts.
- Local Bites & Harborfront Strolls: Beyond the cottages, stroll down Circuit Avenue for warm apple fritters from Back Door Donuts, fresh clam chowder along the harbor, or a ride on the historic Flying Horses Carousel—the nation’s oldest continuously operating platform carousel.

Plan your trip
- Direct Summer Ferry (Peak Season)
- Route: East 35th Street Terminal (Manhattan) → Oak Bluffs Harbor.
- Timing: Runs select weekends from Memorial Day through Labor Day.
- Transit time: Approximately 4.5 to 5 hours aboard a high-speed catamaran.
- Booking: Advance round-trip reservations are strongly recommended via Seastreak.
- Fall & Winter Connection (Off-Season)
- The route: Board an Amtrak train from Moynihan Train Hall at Penn Station to Providence, RI, or Boston South Station, then hop a connecting Peter Pan Bus down to Woods Hole, Cape Cod.
- The crossing: Walk onto the Steamship Authority ferry at Woods Hole, which runs daily, year-round service across Vineyard Sound to Vineyard Haven (45-minute crossing; walk-on tickets available on-site).
- Last mile: From Vineyard Haven, take a 10-minute taxi or local Vineyard Transit Authority (VTA) bus directly to Oak Bluffs.
- Holiday Exception (Thanksgiving Week)
- New Bedford departure: For late-fall travel, Seastreak operates passenger-only holiday runs from New Bedford, MA (about 3.5 hours driving from NYC) to Vineyard Haven over Thanksgiving weekend (November 25–29). MV Vacation
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