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When we tell first-time visitors to leave the car at home, it’s not because we expect them to stay put at our downtown Edgartown hotel. One step off our porch puts you at the center of the action, and walking is our preferred way to get around. Put on your walking shoes (or just your sandals) to explore 10 absolutely essential Martha’s Vineyard attractions within one square mile (read: one easy walk) of Vineyard Square.

 

 

Actual Steps from Our Edgartown Hotel

If you can’t see one of these Edgartown staples from our porch, just look the other direction.

 

1. Chesca’s Restaurant

It’s not uncommon for the aroma of linguine and clams to waft right past our front desk, and we’ll never get tired of bragging about it. Chesca’s has everything we like in a restaurant: spectacular food, an attentive staff, and a comfortable, upscale atmosphere where we always feel welcome.

 

2. Eisenhauer Gallery

Our next-door neighbors have a taste for large-scale paintings with bright colors. Art enthusiasts and casual onlookers alike leave the Eisenhauer Gallery raving about Carol Bennett’s paintings of swimmers and Michel Brousseau’s work with antique boats and automobiles, just two of the many talented artists represented here.

 

Mikel Hunter boutique Edgartown MA 3. Mikel Hunter Boutique

With 25 years in fashion under his belt, Mikel hand picks funky and artisanal clothing, accessories, and artwork that are responsibly sourced and manufactured. Don’t be afraid to ask for suggestions—he has a keen eye for each customer’s style and loves to chat. This storefront is directly out our back door.

 

4. Vineyard Vines

At Vineyard Vines, pastel plaid, pink shorts, and big smiles are the name of the game. Find this authority on island attire right across the street from our Edgartown hotel.

 

5 & 6. Murdick’s Fudge and Mad Martha’s Ice Cream

These sweet neighbors belong together like peanut butter and chocolate. Get your hands on some freshly made fudge at Murdick’s, then stroll over to Mad Martha’s for a specialty sundae like the Oreo Cookie Nookie: Oreo ice cream, hot fudge, marshmallow, and whipped cream topped with a Hershey kiss.

 

Less Than Half a Mile

These Martha’s Vineyard attractions dot the blocks of downtown. All are within five-or-six-minute walk from Vineyard Square Hotel & Suites.

 

7. Martha’s Vineyard Museum

The story of Martha’s Vineyard comes to life at this interactive museum. Our island’s whaling history is front-and-center with permanent exhibits that include a replica of a whaling ship’s tryworks and the Fresnel lens originally installed on Gay Head Lighthouse in 1856.

 

view of Edgartown Harbor from Memorial Wharf8. Memorial Wharf

When you look out at Edgartown Harbor from our hotel’s fourth-floor veranda, you’re looking directly over the top of Memorial Wharf. Walk down Kelly Street, hang a left onto Dock Street, and then climb the stairs of the wharf’s public waterfront pavilion for a panoramic look at the island of Chappaquiddick and the Martha’s Vineyard shoreline.

 

Still Under One Mile

Stretch your legs and venture to the edges of downtown, which are still pretty darn close.

 

9. Lighthouse Beach

The walk up North Water Street to Edgartown Lighthouse is just over half a mile, and with stunning views along the way, it feels even shorter to us. Stately whitewashed colonials give way to tall grasses and sand, with our town’s iconic lighthouse out at the tip of the beach.

10. Bad Martha

Clocking in at .9 miles from our hotel in downtown Edgartown, Bad Martha rewards walkers with refreshing Martha’s Vineyard beer on tap and plenty of seating on the patio and in the tap room. Live music and fierce corn hole competition make this an especially fun afternoon stop.

 
Vineyard Vines — Attractions Near Our Edgartown Hotel

The Ultimate Martha’s Vineyard Holiday Gift Guide
Deck The Island: An Insider’s Guide To Christmas in Edgartown
What’s Your Room Type? 4 Suggestions for Martha’s Vineyard Travelers
Pumpkin Spice and Everything Nice: 4 Ways to Celebrate Fall on Martha’s Vineyard
Scenic Back Roads of Martha’s Vineyard: A Driving Guide
Harvest Time: 6 Top Farm-to-Table Restaurants on Martha’s Vineyard
Island Water Sports: Where to Paddle, Sail, Flyboard, and more on Martha’s Vineyard
Planning a Solo Beach Vacation on Martha’s Vineyard

Whether your idea of a perfect place to propose is jumping out of an airplane or just in your living room, one thing is absolutely certain: you want your proposal to be one to remember. Polish the ring, pick out your spiffiest duds, and let your mind wander with romance because we’ve got 6 places to propose on Martha’s Vineyard sure to knock your love’s socks off.

 

Photo: Unsplash
Photo: Unsplash

 

Places To Propose On Martha’s Vineyard For Every Personality

For the Travel Buffs

If your love gets a thrill from planes, trains, and automobiles, grab lunch or breakfast alongside an unofficial airshow at the Right Fork Diner, located at the edge of the grassy airstrips of Katama Airfield. Chow down as the planes fly overhead, then catch a biplane for a scenic tour from the air and pop the question while flying through the sky.

 

rarebrick_20110403_4230For the Kids at Heart

Embrace your inner child with a proposal on the Flying Horses Carousel. This Martha’s Vineyard fixture is the oldest operating platform carousel in the U.S. — which is just a lovely metaphor for your impending marriage, doncha think?

 

For the Thrill Seekers

Before your hearts beat as one, get them pumping with a thrilling pre-proposal activity. Hop aboard or charter Mad Max Catamaran for a seaworthy excursion across the blue waters of the Nantucket Sound. Looking for a bit more adrenaline? Leap into your future together as you jump from the Memorial Bridge at State Beach. Sure, it’s only a 15 foot jump, but we hear there are sharks in these waters…

 

For the Foodies

For some people out there, deliciousness is next to romance. Grab your foodie significant other and treat them to a tasty morsel before treating them to forever. Our favorite foodie places to propose? Stay in the heart of Edgartown and pop the question on the front porch of Chesca’s Restaurant. For the future fiance with a sweet tooth, stop by the classic Martha’s Vineyard ice cream shop Mad Martha’s for a truly “sweet” moment.

 

Aquinnah Cliffs
Photo: Massachusetts Office of Travel & Tourism

 

For the Traditionalists

If you’re aiming for classic romance, look no further for a place to propose than the beach cliffs at Aquinnah. Pack a romantic picnic and take a stroll. As the sun falls behind the horizon and the water glistens yellow and red, pull the ring out and ask your love for forever.

 

For the Homebodies

Combine the best of Martha’s Vineyard’s romance with the comfort of home. Pop the question in a Vineyard Square Hotel & Suites luxury suite with friends and family waiting outside the door. Then, walk down the stairs to Chesca’s or our outdoor courtyard for a toast to your beautiful future together.

The Ultimate Martha’s Vineyard Holiday Gift Guide
Deck The Island: An Insider’s Guide To Christmas in Edgartown
What’s Your Room Type? 4 Suggestions for Martha’s Vineyard Travelers
Pumpkin Spice and Everything Nice: 4 Ways to Celebrate Fall on Martha’s Vineyard
Scenic Back Roads of Martha’s Vineyard: A Driving Guide
Harvest Time: 6 Top Farm-to-Table Restaurants on Martha’s Vineyard
Island Water Sports: Where to Paddle, Sail, Flyboard, and more on Martha’s Vineyard
Planning a Solo Beach Vacation on Martha’s Vineyard

After months of planning and waiting, it’s finally that time of year again. You’re on your way to your Martha’s Vineyard vacation and nothing can stop you now — well…except for that pesky Woods Hole ferry. Even with the best of intentions, we’ve all missed the ferry to Martha’s Vineyard once or twice. Luckily, your vacation doesn’t have to wait for the next ferry. Jump start your Vineyard vacation with these engaging things to do in Woods Hole.

 

Things to do in Woods Hole Massachusetts
Flickr/Doug Kerr/CC BY 2.0)

Things To Do In Woods Hole, Massachusetts

Embrace the Ocean

Settled over 300 years ago as a fishing and farming community, Woods Hole is internationally known as a center for marine, biomedical, and environmental science. Ocean lovers of all shapes and sizes should head straight for the Woods Hole Science Aquarium, the oldest operating aquarium in the United States. Press your nose against the glass tanks and watch over 140 species of fish waves their tails and flap their fins. Plus, you may even get to graze your fingers across the backs of lobsters, quahogs, spider crabs, horseshoe crabs, hermit crabs, and starfish in the touch tanks — just don’t let the experience turn you off of eating seafood.

 

Nobska Light Woods Hole
Flickr/Mass Travel/CC BY 2.0)

Walk To Nobska Point

Take the long view on your Martha’s Vineyard vacation with a walk down to Nobska Point. Just over a mile away from the Woods Hole Steamship Authority, this gorgeous spot boasts a stunning lighthouse that you may have spotted from the ferry once or twice. Climb to the top of Nobska Point Lighthouse and enjoy panoramic views of Vineyard Harbor and Martha’s Vineyard. Keep an eye on your time though — we wouldn’t want you missing a second ferry, would we?

 

Grab a Snack

If you ask us, one of the best things to do in Woods Hole is to chow down on a delicious snack. Looking to satisfy a deep hunger? Stop into Wood Hole’s favorite pirate bar, the Captain Kidd. Decked out in nautical pirate flair, this spot will get you in the maritime spirit with its decor and decadent fresh seafood. A mere five minutes from the Woods Hole ferry, you’ll find Candy Go Nuts, an old fashion sweets store with a mouthwatering selection. We highly recommend their any of their penny candies for a classic candy store experience. The best part? After all this candy, your kids (and maybe you, too) will crash and nap during your Martha’s Vineyard ferry ride.

 

Take the Shining Sea Bike Path

Bringing your bikes to the island? Scrounge up your helmets and unpack your bikes for a quick trek along the Shining Sea Bike Path. Built along an old railway path, this bike path begins in Woods Hole and extends 11 miles to Falmouth. Unless you’re a very speedy biker (or you’re looking to miss another ferry), we suggest just getting your feet wet, biking along the Cape Cod shore and stopping at the region’s beautiful beaches for a quick dip.

 

With all the quiet corners and maritime gems to discover in Woods Hole, your hour to wait will no longer be wasted. Don’t dilly dally, though. The folks at Vineyard Square are eager to welcome you to your island home.

The Ultimate Martha’s Vineyard Holiday Gift Guide
Deck The Island: An Insider’s Guide To Christmas in Edgartown
What’s Your Room Type? 4 Suggestions for Martha’s Vineyard Travelers
Pumpkin Spice and Everything Nice: 4 Ways to Celebrate Fall on Martha’s Vineyard
Scenic Back Roads of Martha’s Vineyard: A Driving Guide
Harvest Time: 6 Top Farm-to-Table Restaurants on Martha’s Vineyard
Island Water Sports: Where to Paddle, Sail, Flyboard, and more on Martha’s Vineyard
Planning a Solo Beach Vacation on Martha’s Vineyard

If beach time and party time are competing at the top of your vacation to-do list, you’re in luck—Martha’s Vineyard events go on almost around the clock in the warmer months. For those who really want to be at the center of the action, though, a few extra-special dates stand out. These four Martha’s Vineyard summer festivals are just the ticket to add some spice to your days in the sand and sun.

 

Martha's Vineyard summer festivals

 

Martha’s Vineyard International Film Festival

The world’s finest new films make their way to the island toward the tail end of summer, thanks to the Martha’s Vineyard Film Society. The group’s state-of-the-art viewing center in Vineyard Haven hosts favorites from festivals like Sundance and Cannes and screens a few premieres of its own, too. Keep an eye out for works shot on the island—the Film Society nurtures local filmmakers with its “Think Globally, Shoot Locally” campaign. If you can’t visit during the festival but you’re just dying to catch something on the big screen while you’re here, the Film Society and other Martha’s Vineyard movie theaters keep plenty of reels rolling all summer long.

 

MV Book Festival and Author Series

If books are going extinct, we haven’t noticed here on the island. Started in 2009, the Martha’s Vineyard Book Festival is a pretty young tradition for us compared to, say, bass fishing, but it’s fitting in just fine. Writers love the beach as much as anybody, so we’re lucky to have readings, Q & A-sessions, and book signings with famous authors you’d normally have to see in a big city. Note this festival’s alternating formats: every other year, it converges as one big event, while in opposite years, individual readings are presented as a weekly series.

 

Edgartown Fourth of July ParadeEdgartown’s Annual Fourth of July Parade, Barbecue, and Fireworks

This might just be our favorite summer event on Martha’s Vineyard, and that’s only partially because it passes right by us on North Water Street. As a way of saying thanks for spending America’s birthday with us, we reserve our porch and its shaded rocking chairs for registered guests during the parade. Once the flags have gone by, head over to the Dr. Daniel Fisher House lawn, where the Martha’s Vineyard Preservation Trust will be grilling burgers and dogs. Then, after night fall, head down to Memorial Wharf or up to our fourth-floor veranda to watch the fireworks over Edgartown Harbor.

Martha’s Vineyard Agricultural Society Fair

Known to many as a popular Martha’s Vineyard wedding venue, the Ag Hall in West Tisbury hosts a completely different kind of party just once a year, usually in mid-to-late August. We’re talking old-fashioned, farm fresh fun all across the Agricultural Society grounds. In addition to skillet tossing, a shucking contest, and other classic games and rides you’d expect at a top-notch county fair, we highly recommend visiting the Antique Power Museum. It’s full of early engines, tools, and machines that helped island-dwellers get by a century ago, and it doesn’t keep regular open hours except during special events like the fair.

 

These four Martha’s Vineyard summer festivals might be the stars of the event schedule, but the running joke at our Edgartown hotel is that June, July, and August are just one continuous holiday. If you’re feeling festive, give us a call, hop on a ferry, and join the party—any time.

The Ultimate Martha’s Vineyard Holiday Gift Guide
Deck The Island: An Insider’s Guide To Christmas in Edgartown
What’s Your Room Type? 4 Suggestions for Martha’s Vineyard Travelers
Pumpkin Spice and Everything Nice: 4 Ways to Celebrate Fall on Martha’s Vineyard
Scenic Back Roads of Martha’s Vineyard: A Driving Guide
Harvest Time: 6 Top Farm-to-Table Restaurants on Martha’s Vineyard
Island Water Sports: Where to Paddle, Sail, Flyboard, and more on Martha’s Vineyard
Planning a Solo Beach Vacation on Martha’s Vineyard

This probably doesn’t come as a surprise, but our internal compasses are pretty much always pointed towards the beach. Few things are as craveable or satisfying as warming your skin in the hot sun or letting your feet sink deeper and deeper beneath the surface of the sand. No matter what the season, a Martha’s Vineyard beach getaway should always be on the schedule.

 

Martha's Vineyard Beach Vacation

 

5 Martha’s Vineyard Beaches To Explore

South Beach

Known also as Katama Beach, this gorgeous three-mile stretch of sand and ocean is located just three miles away from the Square. Hop aboard your bike or take a stroll down to the water — you’ll find continuous paths the entire length of your journey. Plus, if you travel with your surfboard, ride Katama’s rough waves into surfing glory. Maybe we’re biased because it’s our neighborhood beach, but if you can only hit the sand at one spot on the island, be sure to stop at South Beach on your Martha’s Vineyard beach getaway.

 

Wasque Beach & East Beach

Though our neighboring island, Chappaquiddick, is only a few miles away, it feels like it’s a world apart. Take your bikes or your car across the ferry to Chappy and head to Wasque Beach, located in the Wasque Reservation. Relatively uncrowded and easily accessible, you can enjoy gorgeous, unobstructed views of sand, sea, and sky. Looking for a little more privacy? Make the trek to East Beach, only accessible by bike, hike, or car with four-wheel drive (or minivans with a lot of heart).

 

Menemsha Beach Fish MarketMenemsha Beach

It’s not a Martha’s Vineyard beach vacation without a lobster roll on the beach (and a good, solid sunburn). Just steps from Menemsha Beach, you’ll find food vendors in tiny grey houses selling everything from ice cream to shrimp cocktail. Menemsha just happens to be a working fishing village, so, trust us, you’re in for a treat no matter which vendor you visit. Take your spoils down to the beach during sunset and soak in the colors of the island at this family-friendly spot.

 

Joseph A. Sylvia State Beach

Conquering the island via bike? Joseph A. Sylvia State Beach (aka State Beach) just happens to run along the paved bike path between Edgartown and Oak Bluffs. Ditch the car and pedal to this popular stretch of Martha’s Vineyard beach (some would argue it’s too popular, but trust us, it’s a dream in the shoulder seasons). With smooth waters and (relatively) warm waters, State Beach makes an ideal stop when you’re craving a dip in the ocean. Plus, if you happen to be a movie buff, you can jump off of Jaws Bridge and swim in the Great White’s waters (if you dare).

 

Vineyard Square Beach EquipmentLobsterville Beach

This Aquinnah Beach certainly lives up to its name — a quiet, two-mile stretch of Martha’s Vineyard beach, this spot boasts ample wildlife from sea critters to birds. There’s no parking available on-site, so while it’s not ideal for every Martha’s Vineyard beach-goer, it makes a lovely end to a bike ride or hike to its shores. Wade into the shallow, calm waters of Lobsterville Beach and take in the rainbow colored cliffs of Aquinnah.

 

Your Martha’s Vineyard beach vacation shouldn’t be just sand and surf. After a day warming yourself in the sun, breathing in the salt air, and swimming in the island’s crisp waters, take shelter and relax inside Vineyard Square Hotel. Recharge in your room and then head out for another day of beach fun with our complimentary beach chairs and umbrellas in tow.

The Ultimate Martha’s Vineyard Holiday Gift Guide
Deck The Island: An Insider’s Guide To Christmas in Edgartown
What’s Your Room Type? 4 Suggestions for Martha’s Vineyard Travelers
Pumpkin Spice and Everything Nice: 4 Ways to Celebrate Fall on Martha’s Vineyard
Scenic Back Roads of Martha’s Vineyard: A Driving Guide
Harvest Time: 6 Top Farm-to-Table Restaurants on Martha’s Vineyard
Island Water Sports: Where to Paddle, Sail, Flyboard, and more on Martha’s Vineyard
Planning a Solo Beach Vacation on Martha’s Vineyard