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Martha's Vineyard vacation

There’s nothing better than a Martha’s Vineyard vacation during the summer months. Our idyllic weather, picturesque scenery, and quaint New England charm beckon to tourists from across the globe. Most people may not know that our lovely island hosts a plethora of hiking trails in the Massachusetts countryside. Our staff at Vineyard Square Hotel & Suites highly recommend that you enjoy the summer weather and natural scenery while walking the best hiking trails in Martha’s Vineyard. 

Explore the Best Hiking Trails on Martha’s Vineyard

There’s no better way to start your Martha’s Vineyard romantic getaway than with a tranquil trail around our beautiful island:

  • Caroline Tuthill Preserve Loop is less than two-and-a-half miles long and features a marvelous arrangement of wildflowers.
  • Menemsha Hills Reservation Trail is a moderately trafficked trail that features a staircase leading to the beach. While we advise against swimming, it does provide an opportunity for a pleasant walk along the shoreline. 
  • Tisbury Great Pond Trail is perfect for hiking, trail running, and walking. Take a few moments to survey the pristine lake and keep an eye out for birds and wildlife. 
  • Woodland Wonderland Trail features a leisurely walk around a lake just outside of Edgartown, MA.

While these represent only a few of the best hiking trails on Martha’s Vineyard, there’s a whole list of other walking paths near Edgartown, MA at AllTrails.com.

Our Staff’s Favorite Trails

As you know, a quick Google search can only procure so much information regarding hiking trails in Massachusetts, which is why our staff has put together a list of our favorite paths in the area:

A Massachusetts Getaway You’ll Never Forget 

When you embark on a Massachusetts getaway on Martha’s Vineyard, you’re in for relaxation, rejuvenation, and romance. Luxuriate in our lovely rooms, explore the vineyard, and treat yourself to decadent takeout or delivery dining options. For more suggestions on the best hiking trails on Martha’s Vineyard, please give us a call at 508-627-4711.

Go Exploring with the Best Martha’s Vineyard Tours
Treat Yourself to Fine Dining at the Top Edgartown Spots
Check Out Things to Do in Oak Bluffs on a Memorable Day Trip
Celebrate the Fourth of July with Martha’s Vineyard Events
Live like a New England Local This Spring
Martha’s Vineyard vs. Nantucket: Which One Comes Out on Top
Treat Yourself to Something New at Martha’s Vineyard Shops
A Guide to Martha’s Vineyard Weather through the Seasons

There’s no place like Martha’s Vineyard in the summer: peaceful, green meadows, gorgeous ocean views, fresh seafood, and picturesque lighthouses. You may feel overwhelmed by all of the things you’ll want to do and see when you visit. Consider going on one (or a few!) Martha’s Vineyard tours when you stay at Vineyard Square Hotel. Book a guide for your Martha’s Vineyard vacation or conduct your very own self-guided walking tour. Regardless, you’re sure to learn everything you want to know (and more!) about our Martha’s Vineyard towns.

Learn about Martha’s Vineyard on Foot

One of the best ways to get out and explore a new place is by booking a walking tour. Luckily for you, there are several Martha’s Vineyard walking tours from which to choose. Instead of feeling like a spectator, you’ll be an active participant at places you visit. Plus, it’s a great source of exercise. Edgartown, MA, should be at the top of your list of places to explore. One of the best ways to get an accurate feel of Martha’s Vineyard towns is to book an Edgartown walking tour. Edgartown, MA, is a historical village with a fascinating past and a lively downtown hub of excitement and activity.

Martha’s Vineyard Bus & Trolley Tours

Understandably, not everyone can swing a walking tour. Also, it’s your Massachusetts getaway, so by all means, take it easy. There are plenty of excellent bus and trolley tours (and even a few private charters!) from which to choose. After you’ve narrowed down which Martha’s Vineyard tour (or tours) you want to book, make your way down to Oak Bluffs Harbor, and cruise around our beautiful island.

Martha’s Vineyard Tours & Excursions

If you’re looking for more of a comprehensive sightseeing tour list, then make your way to Martha’s Vineyard Tours & Excursions. Choose between tours that vary by length, create a custom tour, or special request a Jaws tour. Martha’s Vineyard Tours & Excursions will give you an insider’s look at the most beautiful sights and finest attractions our island has to offer.

Self-Guided Martha’s Vineyard Tours

Some people prefer to have structured, guided tours. Others prefer to take tours into their own hands. If you fall into the latter category, consider formulating a self-guided walking tour. Meander the streets of Edgartown or create a lighthouse tour to view our island’s historic structures at your own pace.

Get the Most out of Your Martha’s Vineyard Vacation

Our Martha’s Vineyard towns have so much to offer that will shape your Massachusetts getaway. If you’d like more information on Martha’s Vineyard tours, please contact us. Our knowledgeable staff is happy to assist you.

Go Exploring with the Best Martha’s Vineyard Tours
Treat Yourself to Fine Dining at the Top Edgartown Spots
Check Out Things to Do in Oak Bluffs on a Memorable Day Trip
Celebrate the Fourth of July with Martha’s Vineyard Events
Live like a New England Local This Spring
Martha’s Vineyard vs. Nantucket: Which One Comes Out on Top
Treat Yourself to Something New at Martha’s Vineyard Shops
A Guide to Martha’s Vineyard Weather through the Seasons

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.

Go Exploring with the Best Martha’s Vineyard Tours
Treat Yourself to Fine Dining at the Top Edgartown Spots
Check Out Things to Do in Oak Bluffs on a Memorable Day Trip
Celebrate the Fourth of July with Martha’s Vineyard Events
Live like a New England Local This Spring
Martha’s Vineyard vs. Nantucket: Which One Comes Out on Top
Treat Yourself to Something New at Martha’s Vineyard Shops
A Guide to Martha’s Vineyard Weather through the Seasons

by Rick Conti

Most people, even those too young to remember the show before it went into syndication, recognize those iconic lyrics from the theme song for the iconic Boston-based sitcom “Cheers.”

Martha's Vineyard Beach
It’s not just the beaches! The friendly vibe and sense of place keeps the author coming back to Martha’s Vineyard.

Here’s the line in partial context:

Wouldn’t you like to get away?
Sometimes you want to go
Where everybody knows your name,
and they’re always glad you came.

I have to tell you, that reminds me far more of Martha’s Vineyard than any watering hole.

When I want to get away, that’s where I want to go.  Sure enough, one of the reasons is because, maybe not everybody but, enough people know my name.

One of the many (many, many) great things about Martha’s Vineyard is its manageable size.  It might not seem so when you’re driving from Chappy to Aquinnah, but it’s a small island.  If you spend enough time there, you’ll get to know people: store clerks, business owners, waiters, residents, and, if you misbehave, the local police.  Get familiar with folks, be friendly, and people will get to know your name.  Then (unless you’re a jerk) they’ll be glad you came.

What a great feeling when you walk into a business or other public establishment and people greet you as if you’re Norm from “Cheers”.  It’s as it you’re a celebrity in that little space.  They know you because you come in and you keep coming in because they know you.  That’s pretty cool for everyone involved from my perspective. I must confess I love it when Joanne greets me with her Scottish lilt every time I walk into Vineyard Square Hotel & Suites.

So, I think I’ll keep going back – to the island and the hotel – getting to know more people each time.  Once everybody knows my name, I’ll move on to some other vacation spot, but not a moment before.

If you run into me, make sure to say hello and introduce yourself.

 

Go Exploring with the Best Martha’s Vineyard Tours
Treat Yourself to Fine Dining at the Top Edgartown Spots
Check Out Things to Do in Oak Bluffs on a Memorable Day Trip
Celebrate the Fourth of July with Martha’s Vineyard Events
Live like a New England Local This Spring
Martha’s Vineyard vs. Nantucket: Which One Comes Out on Top
Treat Yourself to Something New at Martha’s Vineyard Shops
A Guide to Martha’s Vineyard Weather through the Seasons