Martha’s Vineyard Vacation Tips from a Longtime Visitor

We dedicate a healthy chunk of this blog to helping first-time visitors learn island basics for planning a classic Martha’s Vineyard vacation — but what about those of you coming back for your second, third, or 30th year? For all who hope to expand their horizons, perfect their timing and planning, and master Martha’s Vineyard like locals, we sat down with a good friend who’s been returning season after season. Sue rides the ferry with the same group of friends every year, and, like many Vineyard veterans, she mixes new adventures into her classic routine on every visit. Even if you’ve heard of some of the Martha’s Vineyard activities below, Sue’s personal tips just might help you get the most out of them.

Sue’s Staples: Classic Martha’s Vineyard Vacation Activities

In addition to the usual downtown Edgartown attractions, Sue’s group usually heads over to Oak Bluffs for at least an afternoon. She insists that Cottage City, home of the island’s famed gingerbread houses, is genuinely worth an afternoon jaunt. We agree — if you haven’t taken a stroll to look at these colorful 19th-century cottages up close, you’ve been missing out (although we certainly understand the urge to stay in Edgartown). It really does feel like you’re in Candyland (minus the threat of Lord Licorice and Glumpy), and you’ll notice new architectural oddities with each visit. The best part? It’s free. Stop in to the Cottage Museum for all the details on how this unique neighborhood came to be.

The Martha’s Vineyard Concert Series is another perennial favorite. Serious artists play to small audiences at the Old Whaling Church, just around the corner from Vineyard Square. Authors, comedians, and other non-musical acts keep the schedule fresh and fun. The MV Playhouse, too, is more than just a rainy day aside — its professional performances belong front-and-center to any Martha’s Vineyard vacation.

A New Discovery: Bowling On-Island

This year, Sue’s group found its way to The Barn in Oak Bluffs and had a ball (many, in fact). This modern bowling alley has quite the cocktail list and is an ideal spot for indoor fun. To the delight of serious bowlers and non-New-Englanders alike, the lanes here use regulation bowling pins and balls — no candlepins in sight.

Sue’s Martha’s Vineyard Restaurant Tips

If a restaurant has lasted more than a year or two on the Vineyard, you can pretty safely bet that it’s excellent. To narrow down your dining list, Sue’s found a couple of stand-outs over the years: she usually eats at Chesca’s at least once or twice — the convenience and creative fare make it irresistible (and it doesn’t hurt that it’s right next door to our Edgartown hotel). The second Martha’s Vineyard restaurant on Sue’s list is less obvious: venture inland from downtown Edgartown and grab a seat at Sharky’s Cantina. Don’t let the casual, unassuming vibe fool you — Sue swears by their steamed cod fish tacos.

Seasonal Hours at Chilmark Chocolates and Other Island Small Businesses

This is neither the first nor the last time you’ll catch us raving about this up-island gem, but Sue had a few sweet ideas even we hadn’t thought of. Sue’s Martha’s Vineyard vacation falls in June, and she usually arrives Saturday or Sunday for a fairly long visit. It’s a perfect time of year to come — we get prime summer weather, and things haven’t hit full-crazy yet since kids are still in school. The only catch is that some businesses, like Chilmark Chocolates, don’t switch to their longer summer hours till later in the month. Sue likes to stop there twice: once at the very beginning of her trip for treats to enjoy on-island, and once right before leaving to pick up gifts and a couple of extra chocolates for the road (a foolproof way to make sure you don’t eat the gifts). The trick, she says, is to time your ferry so you can get to the shop right before their offseason early closing time, while traveling to or from your Edgartown hotel. You’ll avoid crowds and skip making an extra car or bus trip.

P.S. Those seasonal business hours can vary from year to year, and some websites and Facebook pages don’t always keep up. If you’re not sure what’s going on with your favorite shop or restaurant, give us a call while booking your stay and we’ll get you the confirmed local scoop.