Martha’s Vineyard doesn’t have to be a summer-only destination. As the crowds thin and beach towels give way to sweaters, families can discover a quieter side of the island. Fall invites a different kind of getaway, filled with beach walks, animal encounters, and time to enjoy the cooler weather.
Start the Adventure on the Ferry
The fun begins before you even reach the island. The Steamship Authority offers year-round service from Woods Hole to Martha’s Vineyard, with a crossing of approximately 45 minutes. Watch the shoreline recede and let kids look for boats as the island comes into view. If you’re bringing a car, reserve its passage in advance.
Trade Beach Bags for Sweaters
A beach day takes on a different meaning in autumn. Pack layers and head to the shore for a walk, watching the waves and searching for shells along the sand. Invite kids to compare their discoveries: the tiniest shell, an unusual pattern, or a color they haven’t noticed before. For another perspective on the island, contact Island Spirit Kayak about getting out on the water. September and October are shoulder season, with equipment deliveries available by reservation. Ask about options suited to your children’s ages and the day’s conditions.
Leave Room for Island Discoveries
Build each day around one main outing, then leave space for discoveries along the way. Choose a few favorites from these stops rather than trying to fit everything into one weekend.
At Island Alpaca, families can meet dozens of woolly residents and learn about these curious animals. Open year-round, the farm offers a chance for little ones to watch alpacas graze and observe them up close. Leave time to browse the farm shop for cozy alpaca-fiber souvenirs.
The Martha’s Vineyard Museum introduces families to the island through history, art, changing exhibitions, and hands-on displays. For toddlers, the Discovery Room offers tactile exhibits, interactive play areas, and rotating activities designed for young children.
In Oak Bluffs, take a ride on the historic Flying Horses Carousel, where wooden horses and an automatic band organ playing traditional music add to the nostalgic charm. After your ride, stroll down Circuit Avenue and stop for ice cream or a warm cup of cocoa. Confirm fall operating dates before making it part of your plans.
For a taste of the island, stop at Morning Glory Farm in Edgartown. Browse the farmstand for seasonal produce and baked goods and let everyone choose a treat to enjoy together.
Set aside time to explore Mytoi, a Japanese-style garden on Chappaquiddick cared for by The Trustees of Reservations. Follow winding paths and pause by the garden’s pond to look for turtles, frogs, and fish. Along the path to nearby Poucha Pond, watch for ospreys fishing overhead. Getting to Chappaquiddick adds another ferry ride to the adventure.
End the day in Menemsha, where a working fishing harbor meets a beach facing west over Vineyard Sound. Arrive before sunset to watch the boats and stroll along the waterfront. On the jetty, children trying out new fishing poles stand beside seasoned anglers, their silhouettes framed by the fading light. Bring an extra layer and find a spot on the beach as the sky changes color.
Make Lunch an Outing
For an unexpected lunch stop, head to the airport. Plane View Restaurant sits inside Martha’s Vineyard Airport, before security, so you don’t need a flight booked to visit. The restaurant serves breakfast and lunch year-round, with sandwiches, burgers, and seafood among the choices. For children fascinated by airplanes, the setting can make a simple lunch feel like an adventure. Check current hours before heading over.
Find a Comfortable Home Base
For families considering a luxury resort stay, Winnetu Oceanside Resort in Edgartown’s Katama neighborhood offers suites, cottages, and home rentals near South Beach. Check availability for your fall dates and confirm which amenities and children’s activities will be offered, as programming changes with the season.
Pack a favorite card game, bring books for a quiet afternoon, and make dinner a chance to share everyone’s favorite discovery. A fall weekend on Martha’s Vineyard can be as simple as searching for shells, meeting an alpaca, sharing lunch somewhere unexpected, and watching the sun disappear over the water.
