MV’s Best-Kept Secrets

Martha’s Vineyard is known for its stunning coastal landscapes, celebrity sightings, and classic New England charm—but beneath the picture-perfect postcards and sun-drenched beaches lies a quirky side to the island that few visitors ever uncover. Locals know it well: a tapestry of traditions steeped in eccentricity, humor, and heritage.

In this guide, we’re peeling back the curtain on the Vineyard’s most offbeat and beloved customs. Whether you're a first-time visitor or a long-time lover of the island, these unique traditions will deepen your appreciation of Martha’s Vineyard’s one-of-a-kind spirit.

1. The Edgartown Catboat Parade: Sailing in Style

Every summer, Edgartown Harbor transforms into a floating fashion show—if you’re into vintage boats, that is. The annual Catboat Parade is a celebration of these one-sail, wooden sailboats that have glided along New England waters for over a century.

Locals decorate their boats with everything from pirate flags to oversized lobsters, and the best part? The loud cheers from the harborwalk crowd as each vessel floats past, proudly quirky and uniquely Vineyard.

2. Illumination Night: Lanterns, Lore, and a Touch of Magic

A highlight of the summer social calendar, Grand Illumination Night in Oak Bluffs is both heartwarming and wildly whimsical. For one night only, the famous gingerbread cottages of the Martha’s Vineyard Camp Meeting Association are lit from within and without with colorful paper lanterns.

But what makes this tradition quirky? The fierce, silent competition among cottage owners to outshine one another—and the hush-hush family secrets behind custom lantern designs that date back generations.

3. The Chilmark Road Race Costume Craze

You’ve heard of running for a cause. On the Vineyard, some run for laughs. The Chilmark Road Race—a 5K with serious athletic cred—also doubles as an annual excuse to break out banana suits, lobster costumes, and full-on superhero gear.

It’s all about community, fun, and flair. If you can run uphill in a hot dog outfit in August, you’ve earned Vineyard cred.

4. The Black Dog Sticker: The Quiet Island Badge

If you spot a black dog decal on a car bumper, backpack, or laptop, odds are good it belongs to someone with Vineyard roots. What started as a logo for a simple tavern and bakery has become an unofficial island rite of passage.

The tradition? Score your sticker only from the Black Dog store in Vineyard Haven—never online. It’s one of those unwritten local rules, and long-time visitors and islanders know to respect the code.

5. Flying Horses and the Brass Ring Challenge

Oak Bluffs is home to America’s oldest operating carousel, the Flying Horses, and it comes with a twist. As the horses whirl, kids (and nostalgic adults) lean out to snatch a small brass ring from a dispenser. Grab the ring, and you win a free ride.

It’s a humble tradition with big heart—and a rite of passage for Vineyard kids every summer.

6. “Island Time”: More Than Just a Joke

Sure, lots of beach towns joke about running on “island time,” but on Martha’s Vineyard, it’s a lifestyle. Buses arrive when they feel like it, lunch meetings drift lazily into happy hour, and “I’ll be there soon” can mean any time today.

Locals embrace it. Visitors who learn to lean into it find the island far more magical.

Final Thoughts: The Vineyard’s True Personality

While the beaches and boutiques make Martha’s Vineyard a stunning destination, it’s the island’s quirky traditions that make it unforgettable. These offbeat customs reflect a deeper truth: that MV isn’t just a place to visit—it’s a place that lives in you long after the ferry ride home.

So next time you’re here, look beyond the obvious. Join the parade, grab the brass ring, light a lantern—and you might just find yourself part of the tradition.