It’s time to vote for all the things you love most about Martha’s Vineyard with Best of the Vineyard 2025. From beaches, to chowder, to charity events, to ice cream and much more, this is the time to help your Island favorites shine and we hope our Point B Realty Best of the Vineyard 2025 Our Top Picks For Martha’s Vineyard will help you get inspired and plan some fun times ahead on the Island.
The voting deadline is much earlier this year — It runs through March 1st at 11:59 PM EST. With the help of our Point B team, we’ve pulled together a bunch of our favorites. So have a read and head on over to the Best of the Vineyard voting website where you must vote in at least 10 categories in order for your votes to be counted. And if you need to change your entries, no worries, you may modify your ballot at any time prior to the end of voting!

Point B Realty Best of the Vineyard 2025 Our Top Picks For Martha’s Vineyard – Martha’s Vineyard Teddy Bear Suite Fundraiser – Best Charity Event, Best Off-Season Event
When it comes to the Best Charity Event on Martha’s Vineyard it’s our Martha’s Vineyard Teddy Bear Suite fundraiser which raises money for the Martha’s Vineyard Boys & Girls Club! For 2024, Point B hosted our in-person Teddy Bear Suite experience in Nevin Square, at 29 Winter Street, and 19 Winter Street in Edgartown, during the Christmas in Edgartown weekend. The Martha’s Vineyard Teddy Bear Suite has become a cornerstone event for Christmas in Edgartown.
For the last 15 years, we have worked hard to create this special holiday event and have raised over $467,000+ for Food Security programs for the Martha’s Vineyard Boys & Girls Club. The money goes to directly support the MV Boys & Girls Club and their transformative afterschool food programs that support hundreds of Island children and families. If this event delights and inspires you we’d love your vote for the Martha’s Vineyard Teddy Bear Suite for Best Charity Event. The Teddy Bear Suite is also nominated for Best Off-Season Event!
Point B Realty Best of the Vineyard 2025 Our Top Picks For Martha’s Vineyard – Great Outdoors: Best Beach
When it comes to the gorgeous natural landscape that makes Martha’s Vineyard such a special place, it’s hard to pick favorites, as everywhere you go feels like the best place you’ve been. Despite the stiff competition here are some of our Point B Team’s top picks among the Great Outdoors categories:
Best Beach
Check out our guide to Martha’s Vineyard beaches for extra insight and inspiration.
Quansoo Beach. This highly coveted stretch of sand is a private beach in the summer and is the favorite of Point B | Compass Associate Tina Miller.
Lucy Vincent Beach. This Chilmark gem is a favorite of our Vice President of Operations Win Baker, and Reservations Manager Susan Harman Bass.
Moshup Beach. A favorite of Point B | Compass Associate Carson Crissman, who especially loves it for the fishing.
Norton Point. One of the only beaches that allow for oversand access is the top pick for Point B | Compass Senior Associate Jennifer B. DaSilva, Point B | Compass Associate Erin Hegarty, and Point B | Compass Associate Erin Leighton Huckins.
Lamberts Cove. This beloved West Tisbury beach is a favorite of our Social Media Manager Guinevere Cramer.
Menemsha Beach. This Up-Island beach offers some of the best sunsets on the Vineyard and is a favorite of Rental Client Services Manager Heather Kochin. There’s also great fishing and it’s close to some of the Island’s best seafood restaurants.

Point B Realty Best of the Vineyard 2025 Our Top Picks For Martha’s Vineyard – Great Outdoors: Best Nature Walk
Martha’s Vineyard is home to two hundred-plus miles of trails, plus acres and acres of conservation land that make for ultimate outdoor exploration. When it comes to Best Nature Walk our team is hard-pressed to choose between all of our picturesque trails, but the ones that lead to the beach are our favorites! A few personal picks include:
Long Point Wildlife Refuge according to Wendy Harman and Win Baker. We love it for kayaking too!
The Brickyard at Menemsha Hills is a favorite among Carson Crissman and Andrew Noble.
Great Rock Bight is a favorite of Jennifer DaSilva and Erin Leighton Huckins.
Blackwater Pond, located off of Lambert’s Cove Road in West Tisbury is the go-to place to explore for Valerie Hart.
Other staff picks include: Wasque Reservation; Short Cove Preserve; Cedar Tree Neck; Waskosim’s Rock; Caroline Tuthill Preserve; and Felix Neck. Be sure to download the TrailsMV app where you can explore all of the incredible trails of Martha’s Vineyard.
Point B Realty Best of the Vineyard 2025 Our Top Picks For Martha’s Vineyard – Best Real Estate Company Point B Realty
Point B | Compass and Point B Realty Vacation Rentals have been named Best Real Estate Company in the Best of the Vineyard competition for 10 years in a row (and a runner-up in 2014!) and we are so proud of that honor and would love for you to help us make it 11 years.
What sets us apart and makes Point B the Best Real Estate Company on Martha’s Vineyard? A big part of what makes Point B so special is our dynamic and diverse team, who care deeply about serving their clients and their community. They’re passionate and professional. They are some of the best in the business, engaging, supportive, and determined to help make dreams come true on Martha’s Vineyard. As we head into our 16th year as a real estate company, being named Best of the Vineyard continues to be an important accolade for this vision.
We’d love your help in making sure we earn Best of the Vineyard for the Best Real Estate company again this year! You can cast your vote online here through March 1, 2025 at 11:59 pm EST. Please note you must vote in at least 10 categories for your vote to be counted.
Thank you again for helping to make Point B Realty the Best Real Estate Company on Martha’s Vineyard and for sharing your love of all things Martha’s Vineyard!
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