Fall on Martha’s Vineyard: The Island at Its Best

When the summer crowds depart, Martha’s Vineyard reveals a quieter, more soulful side. The pace slows, the air turns crisp, and locals savor a season that feels like a well-kept secret. Autumn here is about golden sunsets over empty beaches, long bike rides on peaceful paths, and hikes that take you through meadows, woodlands, and out to breathtaking overlooks. Add in seasonal festivals, farm stands piled high with pumpkins, dog-friendly beaches, and even a world-famous fishing derby, and it’s easy to see why fall is one of the most rewarding times of year on-Island.

Biking the Vineyard in Autumn

Cycling is one of the best ways to experience the Vineyard in the fall. With lighter traffic and cooler air, it’s easy to ride for miles.

• Manuel F. Correllus State Forest offers more than 14 miles of paved bike paths winding through the 5,300-acre preserve. While it’s more about open pine woods than foliage, it’s perfect for a crisp-weather ride at your own pace.

• Beyond the forest, the Island’s network of paved trails links Edgartown, Oak Bluffs, and Vineyard Haven. Ride along the beach at State Beach, or head inland for quiet farm views and winding lanes.

• For the most dramatic fall color, nothing beats up-Island backroads like Middle Road, North Road, and Lambert’s Cove Road. These routes open to rolling hills, stone walls, and woodlands that truly glow with fall hues.

Whether you’re looking for a short loop or a full day of exploring, biking gives you a front-row seat to the Island’s changing season.

Hiking Trails Worth Exploring

Autumn is prime hiking season on the Vineyard. Trails are less crowded, the air is cooler, and the landscapes are vibrant with seasonal change.

• Menemsha Hills & The Brickyard: One of the Island’s most fascinating hikes, combining woodland trails, open ridges, and the remnants of a historic brickyard along Vineyard Sound. The views from the top are especially rewarding this time of year.

• Waskosim’s Rock Reservation: Rolling meadows, quiet woods, and the iconic glacial boulder that gives the reservation its name. Stone walls wind through the property, offering a glimpse of the Island’s agrarian past.

• Felix Neck Wildlife Sanctuary: A gentler walk, perfect for families or birdwatchers. Trails loop through marshes, shoreline, and woodlands — and fall migrations bring plenty of bird activity.

Fall’s Best Sunset Spots

Few places rival the Vineyard for sunsets, and fall makes them even better: the colors are richer, the beaches are quieter, and there’s room to spread out.

• Menemsha Beach: The quintessential Vineyard sunset. In fall, the crowds are gone, leaving you free to bring a picnic, a blanket, and watch the sky blaze over Vineyard Sound in peace.

• Lambert’s Cove Beach via Land Bank Trail: A newer gem. From Lambert’s Cove Road, the Land Bank has opened a trail that winds past James Pond and leads to the Sound. Parking is limited, but in fall that’s part of the charm. Arrive near dusk and you’ll be rewarded with one of the Island’s most tranquil sunset experiences.

Pet-Friendly Beaches in the Off Season

One of the best perks of fall? The Vineyard’s beaches open up to our four-legged friends. Once the summer restrictions lift, you and your pup can enjoy wide stretches of sand and surf.

Some of our favorite off-season dog-friendly beaches:

• Joseph Sylvia State Beach (Edgartown/Oak Bluffs): Open to dogs October–March, with early morning/evening access in September.
• Lobsterville Beach (Aquinnah): Quiet and remote, perfect for a long, scenic dog walk.
• Lambert’s Cove Beach (Vineyard Haven): Off-season, it’s fully open to dogs and ideal for sunset strolls.
• Norton Point & Eastville Beach: Both allow dogs after summer restrictions lift, offering plenty of open shoreline to explore.

Fishing & The Derby

Fall on the Vineyard means one thing to anglers: the Martha’s Vineyard Striped Bass & Bluefish Derby. This legendary fishing tournament has been running since 1946 and is a cornerstone of the Island’s autumn. For five weeks each September and October, fishermen from near and far cast lines from boat and shore, competing for prizes while celebrating the Vineyard’s fishing heritage.

Even if you’re not an angler, the Derby is fun to experience — from watching the daily weigh-ins in Edgartown to simply feeling the energy it brings to the Island. For many Islanders, fall isn’t complete without it.

Sailing & Golf: Autumn Recreation

Just because summer has ended doesn’t mean the Vineyard’s outdoor recreation stops.

• Sailing & Charters: Many operators still run into fall, offering harbor sails or sunset cruises. Seeing the coastline bathed in golden autumn light is unforgettable.

• Golf: Fall is prime time for a round — clear skies, crisp air, and far fewer players on the greens. Courses like Farm Neck combine natural beauty with challenging play, making it a favorite among both locals and visitors.

Fall Festivals & Island Traditions

The Island’s community spirit shines in autumn, with gatherings that celebrate harvest and local flavor.

• Pumpkin Festival at Morning Glory Farm: A beloved tradition featuring pumpkins, hayrides, baked goods, and plenty of seasonal charm.

• Food & Wine Events: From chef dinners to vineyard tastings, fall is a foodie’s dream on the Island.

• Agricultural Society Harvest Events: Celebrate the Vineyard’s farming roots with family-friendly activities and local produce.

Why We Love Fall on Martha’s Vineyard

At The O’Hanlon Group, we often say fall is when the Vineyard truly belongs to those who love it most. The bustle of summer fades, the beauty feels more intimate, and it’s easy to picture what Island living could mean for you — whether it’s a seasonal retreat or a year-round lifestyle.

Curious about making Martha’s Vineyard your home? Reach out to The O’Hanlon Group | Compass. We’d love to share more of our favorite spots and help you find your perfect place on-Island.