Four-legged family members are always welcome on Tradewind Aviation flights, but as every dog owner knows, hotels, restaurants, beaches, and stores aren’t always as accommodating. Here, find out how you can have the ultimate stay on Martha’s Vineyard and never have to leave Fido behind.

Where to Stay

Photo: Harbor View Hotel

Photo: Harbor View Hotel

It’s a dog’s world, and we’re simply living in it at Harbor View Hotel in Edgartown. Canine guests are showered with amenities through the Island Dog Package — treats and toys by famed island retailer The Black Dog greet upon arrival (plus, mom and dad get a Vineyard Seadogs calendar.)

Pooches love the residential-style Captain’s Cottages, where a living and dining room, kitchenette, separate master bedroom, and expansive balcony offer plenty of space for discovery, indoor fetch, and cuddles.

Canine guests can also laze days away on The Great Lawn, a spacious and grassy social spot at the property’s core, or chill on the wrap-around porch of the principal 1891 historic building while human companions enjoy a good read — or simply the view — from one of the many ocean-facing rocking chairs.

Where to Eat

Photo: Alchemy

Photo: Alchemy

Begin your days at Espresso Love. Strong lattes and fresh-baked croissants (especially the almond variety) go well with mornings of doggie socializing — the patio here is equally popular with humans and canines in the morning. The café also serves light fare throughout the day.

Alternatively, hang out on the al fresco terrace of Behind the Bookstore, a pet-friendly coffee shop and bistro directly behind Edgartown Books. In the morning, opt for a “Café Shakerato,” a frothy coffee drink with orange bitters, or an iced mint latte complemented by a sandwich from the “bagel bar.” Past noon, try the poached local scallop bowl over spring pea puree, washed down with an artisanal cocktail like the “Eazy Breezy,” a refreshing mix of hibiscus vodka, lime, elderflower, ginger, and sparkling wine.

For dinner, book a table on the patio at Alchemy, an Edgartown institution that just revamped the menu and wine program on the eve of its 20th anniversary. Though Fido won’t be able to appreciate the elevated wine list (curated by noted wine advisor Jamie McNeely) or the award-winning cocktail list (recipient of “Best Cocktails on the Island” by Martha’s Vineyard magazine), he’ll likely learn new tricks for a bit of leftovers. Expect lots of tail wagging after scraps of the Pan Seared Striped Bass, the Crispy Roasted Half Chicken, or the filet of Beef Tenderloin.

Where to Shop

Retail therapy isn’t just for humans on Martha’s Vineyard. Dogs can shop for fashionable leashes, raincoats, bowls, mugs, and other trinkets and toys at Good Dog Goods in Oak Bluffs. However, the highlight of any visit here is a treat from the doggie bakery, which sells delectable — and adorable — cookies fashioned after lobsters, whales, and lighthouses.

Dogs are also welcomed at all outposts of The Black Dog stores across the island. This iconic retailer, which hails from Martha’s Vineyard, is known nationally for its black-emblazoned merchandise and has stores in Edgartown, Oak Bluffs, and Vineyard Haven as well as a circa 1971 tavern in Vineyard Haven, where dogs are welcomed outdoors.

Where to Play

A dog plays on a beach in Martha's Vineyard

You’ll need a PhD in beach rules and regulations to know which Vineyard swathes you can stroll with your dog (read: the best thing to do is to consult the concierge at the Harbor View Hotel and pay attention to the beach signs).

At Eastville Point Beach and Norton Point Beach, for example, dogs can roam free outside of tourist season and nesting season (September 15 to March 31.) From April 1 to August 30, dogs are prohibited within 100 yards of a posted nesting habitat, and from May 15 to September 15, dogs are prohibited on the beach between 9 am and 5 pm. So, it’s still entirely possible to enjoy a morning sunrise walk or early evening sunset walk down from Fuller Street Beach (right behind the Harbor View Hotel) to Edgartown Lighthouse Beach, anytime of the year.

For outdoor summertime fun without limits, head to the 72-acre Trade Wind Fields Preserve in Oak Bluffs where dogs can enjoy forested walking trails leash-free – and likely make a few new friends along the way. Alternatively, take the Chappy ferry to Cape Poge Wildlife Refuge, underscored by seven miles of barrier beach and a grove of hundred-year-old red cedars. Year-round, dogs are allowed throughout the refuge as long as they remain on-leash.


Tradewind offers regularly scheduled shuttles to Martha’s Vineyard from May through November – with up to 15 flights per day Thursday through Monday – as well as private charters year-round.


Featured Photo: Harbor View Hotel