Martha's Vineyard without making travel feel impossible.
A practical plan to get parents from Buffalo, and the rest of us plus the dog, onto the island with Friday off, a calmer ferry plan, and lodging that feels like a worthwhile family compromise.
Simple version
Buffalo Drive east
New Bedford or Woods Hole Park on mainland
Oak Bluffs / Vineyard Haven Walk-on ferry
Sep 4-7Friday to Labor Day Monday, using one day off.
3 nightsMore island time and much less punishing travel.
Dog okUse ferry and lodging options with explicit pet policies.
The Short Answer
The best balance is to make this a Friday-to-Monday island weekend, drive to the mainland ferry, walk on with luggage and the dog, and stay in Oak Bluffs or Vineyard Haven so nobody needs an island car.
Recommended
Family plan: Friday, September 4 to Monday, September 7
Everyone takes Friday off. Parents leave Buffalo early Friday, park on the mainland, take an evening ferry, and stay three nights on the Vineyard. The extra night costs more, but it turns Saturday into a real island day instead of another logistics day.
Best mainland ferry target for Buffalo travelers: New Bedford Seastreak, because parking is straightforward and it avoids the deepest Cape traffic.
Best dog-safe fallback: Steamship Authority from Woods Hole, because its pet policy is very clear and the crossing is short.
Best lodging style: a two-bedroom suite, townhouse, or small pet-friendly rental in Oak Bluffs or Vineyard Haven.
Budget fallback
Shorter version: Saturday, September 5 to Monday, September 7
If lodging is painfully expensive, this can compress to two nights. It saves one hotel night, but it makes Saturday a long Buffalo-to-ferry travel day and leaves only Sunday as a full island day.
Better for budget, worse for comfort.
Parents need an early start and a generous ferry buffer.
Only choose this if the three-night lodging cost is the deciding issue.
Why Walk On Instead Of Taking A Car
The island car sounds convenient until the vehicle reservation, ferry cost, and holiday-weekend logistics show up. For this trip, mainland parking plus walk-on ferry is the cleaner family compromise.
Choice
Why it works
Tradeoff
Walk-on ferry
Cheaper, flexible, dog-compatible on the right ferry, and avoids vehicle reservation scarcity.
Pack lighter and stay somewhere walkable or bus-friendly.
Bring one car
Useful if someone has mobility limits or the lodging is far from town.
Steamship Authority vehicle reservations are required in advance, and Labor Day weekend space can be tight.
Fly to MVY
Fastest for your household if schedules and pet rules line up.
Usually not budget-friendly for Buffalo parents, and pet booking needs airline confirmation.
Important: if anyone wants a car on the island, decide early. Steamship Authority says advance vehicle reservations are required for Martha's Vineyard vehicles, while passengers without vehicles can buy traditional ferry tickets at the terminals or digitally.
Suggested Itinerary
This is written so the in-laws can picture the trip without needing to decode ferry systems.
Travel day: Buffalo to ferry, ferry to Oak Bluffs or Vineyard Haven
Parents leave Buffalo early, plan for a full driving day with stops, and aim for New Bedford or Woods Hole with a healthy buffer. The practical goal is to arrive on the island Friday night, check in once, and wake up Saturday already on vacation. If using Steamship Authority from Woods Hole, the crossing to Martha's Vineyard is about 45 minutes; if using Seastreak from New Bedford, re-check the exact Friday holiday-weekend sailing times before buying.
First full island day: settle in, keep it easy
Use Saturday for a slow start, groceries or breakfast near the lodging, Oak Bluffs gingerbread cottages and harbor, and a low-effort beach walk. This is the big reason Friday is worth taking off: nobody has to spend Saturday anxiously watching traffic and ferry times.
Second full island day: Edgartown or beach day
Make Sunday the one planned outing: Edgartown for a stroll and dinner, State Beach or Inkwell Beach, or a longer scenic loop if the group has energy. If staying in Vineyard Haven, start there and use the bus or a taxi for one clean excursion.
Return day: leave enough room for holiday traffic
Take a mid-day or afternoon ferry back to the mainland. Seastreak's current holiday schedule for September 7 shows several Oak Bluffs to New Bedford options, including 1:00 PM, 3:45 PM, 5:10 PM, and 7:45 PM departures. For the Buffalo drive, earlier is kinder.
How Everyone Gets There
There are two serious ferry paths. Pick based on dog policy comfort, parking preference, and available sailing times.
Best for Buffalo budget
Option A: Drive to New Bedford, take Seastreak to Oak Bluffs
This is likely the easiest mental model for the parents: one long drive, park in New Bedford, fast passenger ferry, arrive directly in Oak Bluffs.
Seastreak lists 2026 New Bedford to Martha's Vineyard tickets as available and seasonal service from April 16 to October 12, 2026.
Current one-way adult fare listed: $49; round trip: $84, before booking/fuel/surge details.
New Bedford parking: valet is listed at $30 per day, with holiday valet at $40 per day for September 4-7, 2026; offsite parking is listed at $15 per day with shuttle.
Pet note: Seastreak's general onboard pet FAQ welcomes dogs and cats on many trips, but says pets must stay on outdoor decks unless small dogs are in carriers. Reconfirm for this exact route before buying.
Dog-safe fallback
Option B: Drive to Woods Hole, take Steamship Authority
This is the most official, year-round route and the only ferry operator to carry vehicles if you later decide one car must come along.
Steamship Authority says Woods Hole to Martha's Vineyard takes about 45 minutes.
It says pets are welcome on ferries free of charge, leashed or in a container, with no pets on seats/tables or in food service areas.
Walk-on passengers can buy Martha's Vineyard traditional ferry tickets at terminals on the day of sailing or via eFerry.
Tradeoff: driving deeper onto the Cape can be more traffic-sensitive on a holiday weekend.
For your household plus dog: use the same ferry target as the parents unless flights are dramatically better. A shared ferry arrival makes luggage, check-in, and the first dinner much easier.
Where To Stay
The sweet spot is not the fanciest hotel. It is a place that lets four adults and one dog sleep comfortably without needing a car every time someone wants coffee.
First check
Island Inn, Oak Bluffs
Good compromise profile: suites and townhouses, kitchens or kitchenettes, pet-friendly stays, pool, and near Oak Bluffs without feeling like everyone is squeezed into hotel rooms.
Very practical if arriving by Steamship Authority into Vineyard Haven. The site says it is a stroll from the ferry and has a limited number of dog-friendly rooms.
For four adults plus dog, a two-bedroom rental can beat two hotel rooms. Search Oak Bluffs or Vineyard Haven first; only go farther out if you are comfortable using buses/taxis.
Booking rule: choose lodging before ferry tickets if you are not bringing a car; choose ferry vehicle space before lodging if you decide to bring a car. Labor Day is too tight to leave the dependency fuzzy.
On-Island Transportation
The goal is to avoid needing a rental car for every small move.
Stay down-island
Oak Bluffs, Vineyard Haven, and Edgartown are the practical towns for this trip. Oak Bluffs is best for Seastreak arrivals; Vineyard Haven is best for Steamship Authority arrivals; Edgartown is beautiful but may add transfer friction.
Use VTA, taxis, and short walks
The Vineyard Transit Authority says it provides year-round public transit bus and paratransit service on Martha's Vineyard. Use it for town-to-town movement, then taxis/rideshare when timing matters or luggage is involved.
Booking Links
Use these to verify live availability, fares, policies, and pet rules before anyone buys anything.