Why September Is the Martha’s Vineyard’s Best-Kept Secret

Ask any Vineyarder and they’ll tell you: September is the true sweet spot for visiting Martha’s Vineyard. The buzz of summer crowds gives way to peaceful beaches, golden light, and a slower island rhythm. Known as “second summer,” this early fall stretch offers warm waters, cool evenings, and a more relaxed Vineyard vibe—making it the perfect time for your Martha’s Vineyard vacation rental getaway.

Why September Shines on Martha’s Vineyard

While July and August often steal the spotlight, September offers some of the island’s best weather. Ocean temperatures are at their warmest, perfect for swimming, paddleboarding, or just dipping your toes in the surf. Days are still sunny and warm, but with less humidity, and evenings are crisp—ideal for strolling through charming towns or enjoying a cozy dinner with friends and family.

Fewer Crowds, More Vineyard

By September, the peak-season crowds thin out, giving you room to breathe on beaches, biking trails, and ferry rides. Reservations at popular restaurants become easier to snag, ferry schedules are less hectic, and island roads are calmer. You’ll experience Martha’s Vineyard as the locals do—unhurried and authentic.

Events & Activities to Enjoy

Second summer doesn’t just mean quiet beaches—it’s also packed with culture, flavor, and fun:

• 🎬 Martha’s Vineyard International Film Festival: An early September highlight, this festival brings global cinema and discussions to island screens.
• 🎨 Vineyard Artisan Festival: Meet local artists and shop for handmade goods at this late-summer tradition.
• 🎣 Fishing: Book a fishing charter to join the action.
• 🌾 Farmers’ Markets: Island farms and markets overflow with late-summer produce and fall harvests.
• 🐐 Local Favorites: Wander the eclectic aisles at Alley’s General Store or spend a charming afternoon with the alpacas at Island Alpaca.

Find the Perfect Stay for Your Group

Whether you’re planning a romantic getaway or a family reunion, you’ll find plenty of options for Martha’s Vineyard vacation rentals in September. Looking for space to gather multiple families under one roof? Check out our large homes for rent. Or, if you prefer staying close—but not all in one place—our group accommodations are a perfect solution for keeping everyone together, but with plenty of privacy.

Make the Most of Martha’s Vineyard’s Second Summer

If you love the Vineyard but prefer a calmer pace, September is your season. Between the warm ocean, vibrant island events, and peaceful nights under the stars, second summer offers the best of both worlds. Book your Martha’s Vineyard vacation rental now and discover why locals say September is the island’s best-kept secret.