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Blog :: 03-2022

The Five Essential Things to do on Martha's Vineyard

Martha’s Vineyard has so much to do that you might end up finishing your trip with some activities that you didn’t have a chance to get done. With so many different options for visitors to the island, we’re going to run down the essential activities to do on Martha’s Vineyard whether you’re making the trip in summer, fall, winter, or spring. Better yet, if you time things out just right you can do all of these in one day!

 

Visit the Gay Head Cliffs

Perhaps the single most important destination for your trip to Martha’s Vineyard, no visit to the island is complete without seeing the Gay Head Cliffs! The cliffs themselves have been a tourist attraction since the 1800s and are an enchanting blend of multi-colored clay. Wampanoag legend says that the benevolent giant Moshup would throw whales against the cliffs and cook them over his fire to provide the Wampanoag people with food, with the whales' blood staining the cliffs red and Moshup’s fire coloring them black. Visitors are treated to a truly breathtaking view of the cliffs as well as the beach and surrounding ocean beneath them. Make sure to go when it's clear skies for the best picture opportunity!

 

Find Your Favorite Island Beach

Martha's Vineyard is known for its excellent selection of beaches, so you'll need to find your favorite one before you finish your trip. Ultimately, with so many different beaches on the island, your favorite beach is going to depend on what else you’re doing on your vacation. If you’re visiting Martha’s Vineyard in the summer with your family you could fall in love with the Owen Park or Oak Bluffs Town beaches with their close proximity to downtown shopping and dining destinations. If you’re looking to come prepared with food, an umbrella and spend a long time at the beach then Edgartown’s lengthy South Beach might be the place for you. On the other hand, if you’re here in the offseason and aren’t thinking about swimming you might enjoy the more picturesque Lamberts Cove and Great Rock beaches. Regardless of what you’re looking for in a beach, don’t leave the island without picking a favorite.

 

See the Sunset at Menemsha Beach

Have you ever met anyone who doesn’t love a nice sunset? Well, the sunset view at Menemsha Beach is nothing short of legendary. While sunsets anywhere on the island are quite nice, watching the sun slowly descend below the ocean skyline in Menemsha is the perfect way to close out a day on Martha’s Vineyard. The beach around sunset draws a decent crowd and you’ll regularly hear applause when the sun finally sets. Even more so than the Gay Head Cliffs, make sure you’re here on a day with clear skies - it can be pretty disappointing watching the sun slip behind a cloud instead of the ocean skyline.

 

Drive or Bike Beach Road Connecting Oak Bluffs and Edgartown

Another uniquely Martha’s Vineyard style experience, getting up close and personal with this stretch of the island will be unforgettable whether you’re here solo, with your significant other, friends, or family. Beach Road goes on for a while on the island, but the part connecting Edgartown and Oak Bluffs is a thin stretch of road completely surrounded by water on each side. You’ll be treated to one of the best views on the island and even pass by the iconic Jaws Bridge. Also, this entire stretch of Beach Road has a dedicated bike path but be warned that you’re looking at an over two-mile bike ride one way, so you may want to take the cruise in your car if you aren’t up for a longer bike ride!

 

Make the Trip up Circuit Ave Oak Bluffs and See the Gingerbread Houses

Circuit Ave is right in the heart of Oak Bluffs and feels like the “main street” of the entire island, making it an absolute must-see for visitors to Martha’s Vineyard. Circuit Ave has the highest concentration of dining and shopping options on the island ranging from coffee spots like Mocha Motts, the Flying Horses Carousel, plenty of nightlife destinations and you can see it all in just a short stroll. Whatever you’re looking for on Martha’s Vineyard, Circuit Ave is sure to have it. After you’ve explored Circuit Ave a bit, a short detour will take you on a walking tour of the island’s “gingerbread” houses. These brightly colored cottages are all clustered together with an architectural style and colors reminiscent of an old fairy-tale village. While the hundreds of cottages all look similar, there are many unique design and color choices across them as you take a closer look at this signature island destination. Like all of our other activity recommendations, make sure you have space on your phone because you’ll definitely end up with a lot of selfies by the gingerbread houses.


These ideas are all perfect if you’re visiting the island and you’re either short on time or ideas of what to do during your trip. If you’re looking for a place to stay on your upcoming trip to Martha’s Vineyard check out our many rental properties available today. We can’t wait to see you on the island this season!

What to Do on Martha's Vineyard in April 2022

Spring has sprung on Martha’s Vineyard! The days are getting longer, the weather is getting warmer, and the island is starting to look like its iconic summer self. However, even though we’re still a few months away from summertime activities there’s still plenty happening on the island during April. So what is there to do on Martha’s Vineyard next month? Let’s take a look!

 

Exhibit Opening: Wampum - Stories from the Shells of Native America

This upcoming exhibit at the Martha’s Vineyard Museum opens on April 8th and runs through May 8th. The gorgeous purple and white-colored wampum that lucky visitors can find on some of the island’s beaches have a rich cultural significance to the Wampanoag people that have lived in the northeastern US for over 12,000 years! This exhibition is a retelling of history from the indigenous perspective and through a powerful piece of traditional art. It features a one-thousand bead wampum belt made in the style and traditions of the Wampanoag people - a definite must-see for people looking to learn a little more about the history of the island during their stay! Check out more details about the exhibit on the MV Museum website.

 

Spring Into Nature at Felix Neck

A perfect outdoor activity if you have kids ages 5 - 10 joining you on your vacation. Taking place from 4/18 - 4/22 attendees will spend the week exploring different island properties, learning about wildlife, growing food, making crafts, singing songs, listening to stories, and much more. You can register for this event on the Mass Audubon website or by calling 508-627-4850.

 

MVM Nightlife: Island History Trivia Night

Everyone’s done at least one pop culture trivia night, but how well do you know the history of our little island? Taking place on 4/22 at 5:30 PM the Martha’s Vineyard Museum is hosting its first-ever Island history trivia night. This 21+ only event is perfect for repeat visitors who really know the island (or have islander friends that can carry their trivia team). Registration opens on April 1st and each ticket includes two drink vouchers. You can find more information on the MV Museum website.

 

Visit Iconic Outdoor Locations While Avoiding the Summer Crowds

While this idea isn’t something specifically happening in April, the spring season is the prime time to get some amazing pictures at signature island locations like the Gay Head Cliffs, Edgartown Lighthouse, or a Menemsha Beach sunset while avoiding the crowds that come in the summer months! While you might need to wear a light jacket in your pictures, you can enjoy these iconic island destinations to the fullest during an April trip.

 

Bike MS: Ride the Vineyard

Biking around Martha’s Vineyard is its own reward, but on April 30th you can do it to help fight MS! The National MS Society is running one of its Bike MS events on the island offering 18, 30, and 60 mile options for a full day of biking. To date, Bike MS cyclists, volunteers, and donors have raised more than $1.3 billion dollars to put a stop MS and restore what's been lost, and you can join in to help the cause on Martha’s Vineyard! If you aren’t up for a bike ride you can still help out by volunteering too. For more information or to register check out the Bike MS website.


Our list above is just the beginning of what Martha’s Vineyard has to offer for spring time visitors. If you’re still considering whether or not you should make the journey to the island during spring check out our recent blog post on the benefits of a spring vacation to MV. If you need a place to stay for your visit, regardless of the season, take a look at our many rental properties today!

The Towns of Martha's Vineyard: An Overview for the Summer Visitor

Visiting Martha's Vineyard in the summer is something everyone should experience at least once in their lives. The beaches, the nightlife, and the quaint tranquil vibes come together unlike anywhere else in the country. While the island is very small compared to many other places you might go for vacation, each area of the island has its own unique flair and you may find yourself at the end of your vacation wishing you had spent more time in one place or another. To help guide your upcoming vacation we're going to give you an Islanders perspective of each one of Martha's Vineyard's incredible towns. By the end of this article, you’ll have a great starting idea of the unique aspects of each town to guide where you’ll want to spend your time when you visit the island during the summer!

 

Oak Bluffs

Oak Bluffs is where you'll want to spend a lot of time if you're looking to experience the nightlife scene on Martha's Vineyard. While Oak Bluffs is a far cry from any sort of happening downtown destination in major metropolitan cities in the United States, the locals of Martha's Vineyard would certainly call Oak Bluffs “the party town” of the island. Circuit Avenue,  the main downtown destination, hosts the Island's many popular restaurants, dessert spots, and bars.  There's no better place on the island where you can easily walk off a beach and within five minutes be sharing a meal or some drinks with your friends or significant other. Additionally, this is an excellent location to spend time if you're bringing your family and have younger or teenage kids with you as Oak Bluffs has the highest concentration of “kid-friendly”  activities on the island such as an arcade and the Flying Horses carousel, America's Oldest Carousel. And don't forget a freshly baked late-night donut from #BackDoorDonuts.

 

Vineyard Haven

Vineyard Haven is the year-round “hub” of Martha's Vineyard. It's the only town where ferries arrive for the full year, and, as such, is often the location many travelers to the island see first when they arrive. Traditional travel logic in most parts of the United States would say that you don't really want to spend a lot of time in the town nearby the airport/way you traveled into the area you’re visiting. However, that is definitely not the case with Vineyard Haven on Martha's Vineyard. If you're looking for great restaurants and shopping locations with a little bit more of a low-key vibe compared to Oak Bluffs, then Vineyard Haven is a great place for you to spend time. Although Vineyard Haven isn’t a “dry” town anymore it was for many years, and consequently, Vineyard Haven doesn't really have that hustle and bustle nightlife scene you're going to find in Oak Bluffs or even Edgartown. So if you want to split the difference between a fully secluded island experience and having some convenience in shopping destinations nearby then Vineyard Haven is the place to be on your vacation. 

 

Edgartown

Edgartown is a very interesting location on the island. It probably has the best publicly-available beaches when compared to Oak Bluffs or Vineyard Haven with Island favorites, like South Beach, covering a lot of ground to relax and have some fun in the ocean with the potential for the waves to get pretty big. Some Islanders may joke and refer to Edgartown as the “preppy” town on Martha’s Vineyard, and while you might see a few more folks wearing a polo shirt,  no one in the town is looking to turn their nose up at you. Edgartown has some classic Island restaurants such as Dock Street Diner and The Wharf, offers some nightlife activities (though not as many as Oak Bluffs),  and has a great mix of shopping destinations. The vast majority of shopping and restaurant options on Martha's Vineyard are exclusive to the island but Edgartown offers a local Lululemon, in addition to many island exclusive stores, as well if you find yourself in need of some quality yoga pants on your trip!  Edgartown is a great location for shopping and dining on the island,  but unlike Oak Bluffs, and Vineyard Haven, you're not going to be able to walk from the downtown area to a beach so keep that in mind when you're planning your time.

 

Up-island (West Tisbury, Chilmark, Aquinnah & Menemsha)

Why are we combining towns here? Well, a deep dive into West Tisbury, Chilmark, Aquinnah or Menemsha would shine a light on some differences between each of them. However, for the purposes of a traveler trying to take in the feel of the different areas of the island, looking at these three towns as the collective ”Up-island” is much more productive. Staying Up-island offers the absolute peak of tranquility that you can only get on Martha's Vineyard. There's no semblance of a downtown or Main Street type area anywhere Up-island, but that could be a very big benefit depending on what you're looking for on your trip to Martha's Vineyard.  Additionally, the Up-island areas offer the best-in-class beaches Martha’s Vineyard has to offer although some of them aren't open to the public. Also, you can't forget about signature Island destinations like the Gay Head Cliffs or the legendary sunsets on Menemsha beach. If you're looking to unplug completely on your vacation spending time Up-island is the way to go, but just make sure you know that you aren’t going to be able to walk to more familiar downtown settings like Oak Bluffs, Vineyard Haven, or Edgartown from any of these Up-island towns.


Are you ready for some summertime fun and relaxation? If you're in need of a place to stay on Martha's Vineyard make sure to check out our rental properties or if you have any real estate-related questions you can reach out to us directly. We look forward to seeing you on the island this summer!

Buying a Home on Martha's Vineyard

So you’re thinking of buying a home on Martha's Vineyard. Well first and foremost congratulations! Buying a home is one of the biggest, if not the biggest, purchase in someone's entire life. When it comes to buying property on Martha's Vineyard there are some unique considerations to keep in mind compared to buying a home nearly anywhere else in the country. While there are many intricacies unique to each property you might consider there are a few general questions to keep in mind at the start of the process that can help you on your search for the right place to live on the island.

 

At the outset, it's important to understand the Martha's Vineyard real estate market is really unique. Prices from houses can vary wildly from town to town even though the island is such a small place, and the number of properties that are available at any given time that meet your criteria could be much smaller compared to many other parts of the country. Here at Grace Hagerty Real Estate our team of experts is ready to help you navigate this unique and exciting market. For starters, let's take a look at some key considerations for any kind of home purchasing journey here on Martha's Vineyard. 

Perhaps the most important thing to consider here is if this purchase is going to be for a year-round home or summer home. If this is going to be a year-round home you may consider living in areas like Oak Bluffs, Vineyard Haven, or Edgartown as each of these areas are closer to traditional “downtowns” and shopping centers. If you're looking for something more secluded, Chilmark, West Tisbury, and Aquinnah are all wonderful options but may require a bit more of a hike to any downtown style areas here on Martha’s Vineyard.

 

Another closely related topic is whether or not you're buying a home for yourself, you and your significant other, or your family. If you’re living solo or are with your significant other, you may really enjoy the added tranquility and private nature of the “up Island”  towns like West Tisbury, Chilmark and Aquinnah.  However, if you're raising a family on Martha's Vineyard, as the kids get older they will undoubtedly want to meet up with friends at downtown destinations in Oak Bluffs, Vineyard Haven, or Edgartown. It’s important to emphasize that the island is small enough that everything is really just a 20-30 minute car ride away, but you may not enjoy shuttling your teens from Aquinnah to Oak Bluffs regularly if you're thinking of a year-round purchase.

 

A major consideration for any home purchase, but especially one on Martha's Vineyard is if you're looking for a house that's essentially ready for you to move in at the time of purchase or more of a fixer upper. Both of these are totally valid options and naturally a fixer-upper more often than not will carry a much lower price point when compared to a house that's ready to move into on the spot.  However, one thing to keep in mind about a fixer-upper property is that on Martha's Vineyard there are no mega home improvement stores like Lowes or Home Depot for those of you that are looking to do work on a fixer-upper yourself. Instead you will be looking at local non-chain stores for your renovation needs which often carry a higher price compared to the super stores like Lowes or Home Depot.

 

If a lot of this sounds overwhelming, the specifics of Martha's Vineyard life and home purchases feeling a bit foreign to you, then a wonderful option that many folks do before buying a house on the island is renting a place longer-term during the summer season. During an extended rental period you'll be able to get a feel for each of the Island's towns and the unique life-style that comes with living on Martha's Vineyard, whether it's for the summer season or year-round.  You can check out our number of rental properties on our website -  any of which would be perfect for your stay.

 

If you're ready to take the next step in the process of owning property on Martha's Vineyard, please reach out to us on our website or check out our properties available to buy online. The team at Grace Hagerty Real Estate is here to help you on this exciting journey!

 

Why You Should Vacation on Martha's Vineyard During Spring

While Martha’s Vineyard is known as one of the greatest summer time vacation spots, it's all too often that travelers disregard a trip to the island outside of the summer months. With the spring season just around the corner, Martha’s Vineyard is an excellent destination for families, couples, or solo travelers looking for some rest and relaxation. If you’re asking “why should I visit Martha’s Vineyard in the spring?” then we have the answers you need.

 

First let’s address the elephant in the room: the beaches. Perhaps more than anything else, Martha’s Vineyard is known for its array of incredible beaches and many of you might be wondering what’s the point of coming to the island if you can’t enjoy the beaches to the fullest. While we definitely wouldn’t recommend a dip in the ocean during March or April, there's way more to the Martha’s Vineyard beaches than swimming. You can stock up on delicious food in downtown Oak Bluffs and take a 5 minute walk to set up a beach picnic at the Oak Bluffs Town Beach for example. You can skip stones and search for wampum at the Lighthouse Beach in Edgartown, and there’s never a bad day to watch the sunset on Menemsha Beach. So yes, swimming is off the table but just about every other benefit is waiting for you on the shore!

The absolute best reason to visit Martha's Vineyard during the spring is the major difference in population on the island outside of summertime. Since the island is so well-known as a summertime destination things can get very very crowded. The Martha’s Vineyard Chamber of Commerce estimates that the island is “home to roughly 17,000 year-round residents. During the summer months, the population increases to nearly 200,000. Sixty-three percent of all homes on the Vineyard belong to seasonal residents”. That is over a 10x increase in population during the summer months! When you decide to visit Martha's Vineyard in the offseason you get an entirely different level of tranquility compared to the summer, and after the past few years a vacation should be a relaxing time above all else!

 

In the springtime, now that the weather is starting to get much nicer, the many outdoor activities offered by Martha's Vineyard are ready for you to explore -  without the crowds that come with a summertime visit! The famous Gay Head cliffs are open to the public year-round and getting there with your friends and family for some once-in-a-lifetime photos is just so much better when there's no one else in the background. Take a stroll around the gingerbread houses in the campgrounds of Oak Bluffs, or take a bike ride up beach road connecting Edgartown and Oak Bluffs. These are just a few classic outdoor activities that can make your vacation perfect during a spring time visit.


If you're looking for a place to stay on your springtime getaway to Martha's Vineyard make sure to check out our many rental properties or you can reach out to us on our website with any rental inquiries and we'll help you out with whatever you need. If you're already planning a trip to Martha's Vineyard this March make sure to check out our recent blog post on some fun activities you can do on the island during your stay.