The Best Fall Hikes & Bike Rides on Martha’s Vineyard

As the summer crowds thin and the crisp ocean air rolls in, Martha’s Vineyard in the fall transforms into a haven for outdoor adventurers. With vibrant foliage, quieter trails, and mild temperatures, it's the perfect time to explore the island’s natural beauty on foot or by bike. Whether you're a seasoned hiker or a casual cyclist, these top fall hikes and bike rides on Martha’s Vineyard offer breathtaking views, colorful woods, and coastal serenity.

Why Fall is the Ideal Season for Outdoor Adventure

Fall on the Vineyard is often called the island’s “secret season.” The weather is cool but comfortable, the bugs have (mostly) disappeared, and the island is awash in reds, oranges, and golden yellows. It’s an unmatched setting for hiking and biking. Plus, you’ll enjoy the peace of the off-season and the chance to reconnect with nature on uncrowded trails.

 Best Fall Hiking Trails on Martha’s Vineyard

1. Menemsha Hills Reservation (Chilmark)

This rugged preserve offers a diverse trail network through forest, wetland, and open coastal bluffs. The highlight? Prospect Hill, the island’s second-highest point, which provides panoramic views of the Elizabeth Islands and Vineyard Sound. During fall, the changing colors across the hillsides are picture-perfect.

Trail tips:

Bring water-resistant hiking shoes – parts of the trail can be muddy.

Don't miss the Brickyard Trail for a glimpse into the island’s industrial past.

2. Cedar Tree Neck Sanctuary (West Tisbury)

Nestled on the island’s north shore, this sanctuary offers wooded trails lined with oak, beech, and — you guessed it — cedar trees, which turn vibrant shades in October. The trails lead to a serene beach and offer a true escape into nature.

Trail tips:

Quiet and family-friendly

Great for birdwatching in the fall migration season

3. Long Point Wildlife Refuge (West Tisbury)

Managed by The Trustees, Long Point is a stunning mash-up of coastal pond, beach, and woodland trails. In fall, the open landscapes and salt marshes glow under soft golden light, making this one of the best spots for sunset walks.

Trail tips:

Open Thursday–Sunday in fall

Bring a camera for golden hour photography near the ponds

 Scenic Fall Biking Routes on Martha’s Vineyard

1. State Forest Loop

This paved bike path winds through Miles of forest with blazing fall foliage. It’s part of the 10-mile paved network in the Manuel F. Correllus State Forest and is ideal for beginners and families.

Route highlights:

Flat, easy terrain

Connects with Edgartown and Vineyard Haven for a longer adventure

2. Vineyard Haven to Oak Bluffs Coastal Ride

Hugging the shoreline along Beach Road, this ride delivers expansive ocean views on one side and sweeping marshlands on the other. Early morning or late afternoon rides here are spectacular.

Route tips:

Best for sunrise views over Vineyard Sound

Stop at East Chop Light for photos

3. Katama to South Beach (Edgartown)

This scenic 3-mile stretch leads through open farmland and rolling fields, ending at the crashing surf of South Beach. In autumn, the surrounding golden grasses and open skies make it feel like a ride through a painting.

Route tips:

Bring layers—it’s breezy near the beach

Pack a picnic for a relaxing post-ride meal by the dunes

 What to Pack: Fall Hiking & Biking Gear Tips

Layering is key for outdoor fall adventures on Martha’s Vineyard. Here’s what to bring:

Base Layer: Moisture-wicking long-sleeve shirt

Insulating Layer: Fleece or lightweight puffy jacket

Outer Layer: Windbreaker or rain jacket (the weather can shift quickly)

Footwear: Waterproof hiking shoes or sturdy trail runners

Accessories: Gloves, beanie, and a backpack with snacks and water

For biking, consider full-finger gloves and a windproof shell to stay comfortable in breezy conditions.

 Best Fall Sunrise & Sunset Spots on the Vineyard

Sunrise: Joseph Sylvia State Beach (perfect morning colors over Nantucket Sound)

Sunset: Menemsha Beach or Aquinnah Cliffs (unbeatable golden-hour lighting)

Pro tip: Check the tides and sunset schedule before you go, and plan your hike or ride to catch the best light

Final Thoughts

From leaf-strewn trails to wind-swept coastal rides, fall on Martha’s Vineyard is an outdoor enthusiast’s dream. Whether you're seeking solitude in the woods or ocean views from your handlebars, the island’s trails and bike routes deliver unforgettable experiences.

So lace up your boots, grab your bike, and discover the best fall hikes and rides Martha’s Vineyard has to offer.