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Your wedding weekend on Martha’s Vineyard comes with more than rings and vows — you and your guests have the whole wide island to explore. At the same time, we know you’ll be extremely busy before and after tying the knot, what with makeup, photos, and making it on time to your wedding venue. That’s why we’ve come up with this sample wedding weekend itinerary for guests — feel free to include what you see fit as part of a welcome package or guide to the island.

 

 

Edgartown Harbor - Martha's Vineyard wedding weekend activities

 

Our Wedding Weekend Itinerary

Friday: Arrive and See the Island

Depending on what time folks arrive, Wedding Weekend Day One can be full of adventure or just a time to crash and relax. Just because we have island tunnel-vision, we’ll err on the side of a pretty full day of island living:
The closest beach to downtown Edgartown is Lighthouse Beach. Stroll northeast on North Water Street for about seven minutes, and there, you’ll see Edgartown Lighthouse to your right at the end of a sandy pathway. It’s a great place to set up shop for a lazy afternoon.
• For those who want to get out and stretch their legs after traveling, the gently sloping trails at the Caroline Tuthill Preserve offer stunning ocean views and natural scenery.
• Thirsty? Catch up over Martha’s Vineyard craft beers or grab an artisanal cocktail at Alchemy. If you’re ready to roam, here are six more Edgartown nightlife hotspots.

 

Cocktail at Chesca's Restaurant
Another great spot for food and drink: Chesca’s

Saturday: Get Ready on Island Time

Saturday morning doesn’t have to be a big rush just because Saturday night’s the big night — there’s plenty to do without straying too far from your hotel room.
• Start your day at the authentic locals’ diner: Dock St. Coffee Shop.
• Walk around downtown Edgartown. Memorial Wharf is a prime spot for pre-wedding selfies, and you’ll find plenty of boutique shops and galleries to peruse nearby. See our guide for more Edgartown shopping options.
• Saturday also makes a great spa day if you’re so inclined. We recommend Sea Spa Salon for wedding weekend treatments and plenty of primping.

 

Sunday Morning: More than Goodbye

Guests who spend their wedding weekend as part of a Vineyard Square room block are entitled to an upscale continental breakfast with homemade pastries and other treats in the breakfast nook just behind our lobby. We also have a small function room down the hall for some extra seating in private. Weather permitting, however, the best place to gather is on the patio.

 

One of our favorite things we’ve seen newlywed couples do recently is plan some small activity for the whole group to do together before departing. For some, it’s a walk down to the wharf led by the bride and groom. For others, it’s making sure the whole group books the same ferry back to Woods Hole. If you’re scrambling for one last-minute group photo, we’re more than happy to hop out from behind the front desk and click the shutter. Here’s a many magical wedding weekends on the island!

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Martha’s Vineyard is one showstopper of an island with a rich history to boot, and nothing reflects that quite like the island’s golf courses. From the remote allure of the Chappaquiddick Links to the pristine ocean views of Farm Neck, each course is its own beautiful patch of club-swingin’ excitement.

 

Golfing in Massachusetts, Golf Courses in Martha's Vineyard
Photo: Massachusetts Office of Travel & Tourism/CC BY-ND 2.0

 

5 Martha’s Vineyard Golf Courses

 

Royal & Ancient Chappaquiddick Links

As its name suggests, the Royal & Ancient Chappaquiddick Links (or RACL for short), is practically royal in every way. The links were established all the way back in 1887, and are often considered a hidden gem on Chappaquiddick Island. To get there, you have to hop aboard the Chappy Ferry, which runs year-round out of Memorial Wharf in Edgartown, and then aboard the greens keeper’s turquoise VW bus for the ride to the links.

 

The quirky nine-hole course is surrounded by untouched forestry, fitting for the quiet and secluded location. While not generally open to the public, weekly memberships are available, offering unlimited play. We can often arrange tee-times at RACL for guests of Vineyard Square Hotel — just ask!

 

Edgartown Golf Club

Backdropped by beautiful views of the Vineyard Sound and the Trapps Pond, Edgartown Golf Club is just the spot to put your swing to the test while getting those full-fledged picturesque views. It’s also unique in that the club is open to members and their guests year-round, weather permitting. The club also hosts many benefit tournaments during the summer, and a comprehensive junior golf program so that the kids can take a few shots on the green.

 

Farm Neck Golf Course, Links in Martha's Vineyard
Farm Neck Golf Course. Photo: Massachusetts Office of Travel & Tourism/CC BY-ND 2.0

Farm Neck Golf Club


Finally, a golf club with the
presidential seal of approval! Nestled up in Oak Bluffs, Farm Neck Golf Club features 18 holes with a reputation for championship-level quality. Follow the greens through intimate woodlands, beautiful open meadows, salt marshes, and fantastic ocean views.

 

You can satisfy your hunger at the cafe and enroll in lessons if you’re looking to take your first swing. Technophiles, you’ll have a leg up on the competition with a complimentary smartphone app called YamaTrack — it shows your position on the course and yardage to go. You might want to look up while you’re swinging, though!

 

Mink Meadows Golf Club

Away off in the far north (Tisbury), Mink Meadows is conveniently positioned just beyond Vineyard Haven. The clearings of trees that form Mink Meadows were originally made in 1928 as fire lines to prevent wildfire spread. The owner of the property, Robert Bigelow, realized that the clearings looked like fairways and decided to transform the land into a golf course.

 

Mink Meadows caters to both both seasoned and novice players with varying degrees of difficulty in their nine holes. They host a wide variety of events and tournaments with a Ladies’ Day each Thursday, and offer pro shop services and lessons for all ages.

 

Vineyard Golf Club

Vineyard Golf Club may be the newest game in town, but it still has classic design elements that provide fun challenges — take the third hole, which features a devilish sand trap just before the fairway. Just outside of Edgartown, the club was named by GOLF Magazine as the “Best New Private Course” of 2015. The course also draws visitors for being the only organic golf course in the U.S. — no chemical pesticides, herbicides, or fertilizers on these greens.

 

With all of the options to take a swing at, you’ll definitely want to add golf clubs to your packing list for Martha’s Vineyard. The folks at Vineyard Square are more than willing to give you more tips for your trip, so don’t hesitate to ask.

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What do you think of when you think The Vineyard? Playing in the surf, catching some rays, shopping in Edgartown, dining at Chesca’s, and spending a luxurious night at Vineyard Square may all come to mind, but what about hitting Edgartown’s bars? Believe it or not, Edgartown boasts a H-O-P-P-I-N nightlife. Live music, dancing, and wildly creative cocktails abound when the sun sinks below the shoreline. Slip on your dancing shoes and get ready to experience the best of Edgartown nightlife.

 

Martini Glass at Chescas Restaurant | Edgartown Nightlife

 

Dance The Night Away At These 6 Edgartown Nightlife Spots

The Port Hunter

The Port Hunter’s music calendar is always packed with exciting, diverse acts. From rock to folky bluegrass to jazz, nothing is off the table at The Port. Pick up the daily special at the raw bar, throw back a signature cocktail, and get ready to get down at The Port Hunter.

 

The Wharf

Three doors, three different vibes. Behind door number one at The Wharf, find a cozy pub atmosphere, boasting twelve different beers on tap and a relaxed, social energy. Behind door number two is The Restaurant: family-friendly and offering lunch and dinner seven days a week. Finally, behind door number three is one of the most hoppin’ spots in town: The Back Bar. Offering a full bar, live music, DJs, parties, karaoke, and more all summer long, head to the Back Bar after dinner to to get the real lowdown on Edgartown nightlife.

 

Beer Taps At An Edgartown Martha's Vineyard BarAlchemy

Winner of Martha’s Vineyard Magazine’s Best Cocktail, Alchemy in Edgartown offers top notch drinks and an upstairs porch with a view of Main Street. Order an Autumn Old Fashioned, a Benni Bellini, or an Espresso Martini, and relax in this upscale eatery and bar.

 

The Newes From America Pub

A genuine New England pub and classic Edgartown bar, the Newes offers a huge selection of beers and cocktails. This popular dive is right in the middle of Edgartown, and just across the street from Vineyard Square Hotel. Have drinks at the bar after dinner, chat with old friends, and make some new ones at this laid-back spot.

 

Seafood Shanty

Hit up the Seafood Shanty for live music and DJs on the weekends. Enjoy dancing and frequent themed parties, accompanied by a classic cocktail, such as a Mojito or a Dark and Stormy, or maybe something a little wild, like the signature Stumbling Islander (we know, you may have earned this title a time or two). The Shanty is a staple of Edgartown nightlife — every townie knows it!

 

The Atlantic Fish and Chop House

If you’re looking for things to do in Edgartown, look no further: this is the place to go for a night of great live music and killer drinks. The Atlantic’s cocktail and wine menu is prolific, and they offer the best in local seafood dishes with an haute cuisine twist. Not feeling fishy? No worries. Order one of their killer chophouse classics like the Filet au Poivre or the Cajun Ribeye, or maybe go for the Foie Gras Burger or the Osso Bucco. Whether you’re there to eat, drink, or party (or, c’mon, all of the above), The Atlantic offers a little bit of everything, adding some spice to Edgartown nightlife.

 

No matter where you end up, make your way back to a comfy bed at Vineyard Square Hotel, right in the heart of Edgartown. There’s nothing like soft sheets and the promise of a fresh breakfast to cure what ales you after a wild night out on the town!

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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

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.

 

Gingerbread Cottages in Oak Bluffs | Martha's Vineyard Vacation Attractions

 

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

Sharky's Cantina Martha's Vineyard restaurant
Photo: 6SN7 via Flickr

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.

A Guide To: Martha’s Vineyard Beaches Around Edgartown
Dig In and Dine Out: A Guide to Year-Round Edgartown Restaurants
The Spa Next Door: Services From Our Favorite Martha’s Vineyard Spa
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

With so many things to do in downtown Edgartown, it can be tough to justify straying very far from North Water Street, especially on a shorter visit. Still, if you’re a veteran of these parts or just looking for a change of scenery, a trip up-island is well worth your time. When we say up-island, we mean the western part of Martha’s Vineyard: West Tisbury, Chilmark, Menemsha, and Aquinnah. Confused yet? The phrase “up-island” dates back to our whaling days, when latitude and longitude were crucial for navigation. The further up-island you go, the higher your coordinate of longitude.

 

Gayhead Light Atop The Aquinnah Cliffs

Getting Up-Island from Edgartown

We’ll admit that heading up-island takes a bit more planning and travel time than a stroll to Edgartown Lighthouse, but, trust us — the extra effort pays off. These smaller towns run at a slower pace, with natural scenery as their main focal point. For a quick ride out of town, your best bet is to check out the Vineyard Transit Authority bus schedule — day passes are inexpensive, and buses run regularly from town to town all day during the summer. For total freedom at a higher price, you can charter your own Stagecoach Taxi for your person tour-de-island. Guests can always stop by the front desk for personalized help planning a day up-island.

 

There’s a lot of ground to cover over in those parts, but we consider these up-island attractions essential:

 

West Tisbury

A perfect stop on the way to or from the island’s western tip, West Tisbury’s limits reach the shore both north and south of downtown, covering a huge swath of central-western Martha’s Vineyard. With the people here scattered few and far between, this hamlet provides the perfect opportunity for a meandering stroll through nature.  Just outside the village lies the 70-acre Polly Hill Arboretum, where tree species from around the world thrive amidst beautiful stone walls and meadowlands. Split your outdoor time between the Arboretum and the Field Gallery, whose whimsical sculptures live in harmony with a green landscape.menemsha beach light guard stand

 

Menemsha

For hundreds of years, the island’s freshest catches have been arriving daily from the tiny fishing village of Menemsha. Larsen’s Fish Market menu has all the classics cooked to order from clam chowder and lobster to stuffed scallops. Visit for lunch or stop by mid-afternoon to avoid the evening rush that accompanies Menemsha’s famous sunsets. A walk around this sand-swept town promises rewards in the form of lesser-known storefronts, ocean views, and solitude.

 

Chilmark

Chilmark chocolates sign on Martha's VineyardJust southeast of Menemsha, Chilmark is the place to stock up on farm-fresh up-island produce and treats. Chilmark Chocolates make a sweet gift (if you can resist eating them yourself), and the Chilmark General Store serves up top-notch breakfast sandwiches and gourmet pizza with seating on their covered porch. Expect a fair amount of company at both places — they’ve earned the fuss.

 

Aquinnah

Home to the famed Gay Head Lighthouse, Aquinnah marks the westernmost tip of Martha’s Vineyard. You’ve probably seen photos of this historic beacon atop copper-colored clay bluffs, but a camera just can’t do it justice. The shoreline changes constantly with the tides—so much so that the lighthouse has actually been moved back from its more precarious original location.

A Guide To: Martha’s Vineyard Beaches Around Edgartown
Dig In and Dine Out: A Guide to Year-Round Edgartown Restaurants
The Spa Next Door: Services From Our Favorite Martha’s Vineyard Spa
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