At a Glance: Martha’s Vineyard in September
- Weather: Ocean temps and sunshine extend right into September — warm enough for beach days, crisp enough for sweaters at night.
- Crowds: Fewer than peak season, letting you experience the Vineyard at a slower, more authentic pace.
- Top Events: MV International Film Festival, MV Striped Bass & Bluefish Derby, Tivoli Day, Vineyard Artisan Festival.
- Travel Tip: September is ideal for reunions, weddings, and group getaways — book large Martha's Vineyard rentals early.
- What to Pack: Layers, comfortable walking shoes, and an appetite for farm-fresh food and local festivals!
September on Martha’s Vineyard is what locals call “Second Summer” — and it might be the island’s best-kept secret. I’ve been to the Vineyard in September several times and it really is a treat. The warm sunshine still makes for proper beach days, the traffic is lighter if you’re driving, and the restaurants — which had you waiting an hour all summer — suddenly have open tables again. The island settles into something quieter, more genuine, and more beautiful than you’d expect.
Behold the incredible views at the Aquinnah Cliffs.
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.
Enjoy the beaches without the peak-summer crowds.
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.
- The Striped Bass & Bluefish Derby: An 80+ year island tradition that transforms the fishing community and is fascinating to witness even if you've never picked up a rod. One of the oldest fishing tournaments in New England.
- 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. I’ve enjoyed both myself and highly recommend adding them to your itinerary!
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.
A second summer stay means more space, less stress, and unbeatable island charm. Find your perfect vacation rental with WeNeedaVacation and enjoy NO booking fees!
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.